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Bile acid

(total 674)
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No Structure COMMON NAME NAME DATA No INFORMANT SYMBOL FORMULA MOL.WT(ave) Download BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINT BOILING POINT DENSITY REFRACTIVE INDEX OPTICAL ROTATION SOLUBILITY UV SPECTRA IR SPECTRA NMR SPECTRA MASS SPECTRA OTHER SPECTRA
1
Ursocholanic Acid
5b-Cholan-24-oic Acid
 BBA0001
Takashi Iida
C24H40O2 360.573 Download ChemDraw structure file

164degC, (Me ester; mp, 86degC)(Ref. 0001/0002)
[a]14D: +21.74deg (CHCl3)(Ref. 0001/0002)
[a]D: +23.2deg (dioxane) (Me ester)(Ref. 0001)
nmaxm: 9.68, 10.58(Ref. 0003)
Me ester: nmaxm: 9.65, 9.88, 10.60(Ref. 0003)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 21-Me 0.90(d), 19-Me 0.91(s)(Ref. 0004/0005)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.2, C-3 26.9, C-4 27.4, C-5 43.6, C-6 27.1, C-7 26.4, C-8 35.7, C-9 40.4, C-10 35.2, C-11 20.7, C-12 40.2, C-13 42.6, C-14 56.5, C-15 24.1, C-16 28.0, C-17 55.8, C-18 11.9, C-19 24.1, C-20 35.2, C-21 18.1, C-22 30.8, C-23 30.8, C-24 174.2, C-25 51.1(Ref. 0004/0006)
Me ester (22eV) m/z: 374(M+), 359(M-CH3, 100%), 343(M-CH3O, 2%), 325(M-CH3O-H2O, 5%), 317(4%), 278(M-ring A, 5%), 264(M-ring A and C-6, 12%), 259(M-SC, 1%), 257(M-SC-2H, 1%), 249(M-ring A and C-6-CH3, 1%), 232(ABC ion, 15%), 217(ABC-ring ion, 100%), 203(11%)(Ref. 0039)
The spectrum (70eV) was shown as the Me-ester derivative(Ref. 0007)


Isolated from the embryo of the jequirity bean, Abrus precatorius.(Ref. 0001)
Detected as a trace component of human feces.(Ref. 0101)




[0001] / [0002] / [0003] / [0004] / [0005] / [0006] / [0007] / [0039] / [0101]
2
Allocholanic Acid
5a-Cholan-24-oic Acid
 BBA0002
Takashi Iida
C24H40O2 360.573 Download ChemDraw structure file

170degC, (Me ester; mp, 91degC)(Ref. 0001/0002/0237)
[a]14D: +21.74deg (CHCl3)(Ref. 0001/0002/0237)
[a]D: +22.1deg (Me ester)(Ref. 0237)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 19-Me 0.77(s), 21-Me 0.90(d)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d : C-1 38.6, C-2 22.1, C-3 26.7, C-4 29.0, C-5 46.9, C-6 29.0, C-7 32.0, C-8 35.4, C-9 54.7, C-10 36.1, C-11 20.7, C-12 40.0, C-13 42.5, C-14 56.5, C-15 24.0, C-16 28.0, C-17 55.8, C-18 11.9, C-19 12.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.2(Ref. 0011)
The spectrum (70eV) was shown as the Me-ester derivative(Ref. 0007)


Detected in the biliary bile from alligator mississippiensis.(Ref. 0209)




[0001] / [0002] / [0007] / [0008] / [0011] / [0209] / [0237]
3
Lithocholic Acid
3a-Hydroxy-5b-cholan-24-oic Acid
 BBA0003
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

186degC(Ref. 0001)
130-132degC (Me ester)(Ref. 0040)
[a]d-20: +33.7deg (C=1.5, MeOH)(Ref. 0001)
nmaxm: 9.72, 10.60(Ref. 0003)
Me ester: nmaxcm-1: 1721 (C=O), 3610 (OH), 1106, 1010, 725(Ref. 0040)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 19-Me 0.88(s), 21-Me 0.88(d), 3b-H 3.5(brm)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.0, C-2 30.1, C-3 71.0, C-4 36.0, C-5 41.8, C-6 26.9, C-7 26.2, C-8 35.5, C-9 40.1, C-10 34.2, C-11 20.5, C-12 39.9, C-13 42.4, C-14 56.2, C-15 23.9, C-16 27.8, C-17 55.6, C-18 11.7, C-19 23.1, C-20 35.1, C-21 17.9, C-22 30.7, C-23 30.7, C-24 174.2, C-25 51.0(Ref. 0006)
Me ester (70eV) m/z: 372(M-H2O, 78%), 357(M-H2O-CH3, 17%), 257(M-H2O-SC, 23%), 248(M-SC-part of ring D (27), 10%), 230(M-H2O-SC-27, 29%), 217(M-173, 42%), 215(M-H2O-SC-ring D (42), 100%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Occurred in ox, moneky, rabbit, and pig bile.(Ref. 0001/0101)
Identified in human blood and feces.(Ref. 0101)
Bacterial 7-dehydroxylation product of chenodeoxycholic acid and ursodeoxycholic acid.(Ref. 0102)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)




[0001] / [0003] / [0005] / [0006] / [0007] / [0009] / [0010] / [0040] / [0101] / [0102] / [0150] / [0151]
4
Isolithocholic Acid
3b-Hydroxy-5b-cholan-24-oic Acid
 BBA0004
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

176-176.5deg, (Me ester; mp, 117.1-118degC)(Ref. 0001)
[a]D: +32deg (CHCl3), [a]D: +21.3deg (CHCl3) (Me ester)(Ref. 0001)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 21-Me 0.91(d), 19-Me 0.95(s), 3a-H 4.06(m)(Ref. 0004/0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.8, C-2 27.8, C-3 66.7, C-4 33.4, C-5 36.3, C-6 26.5, C-7 26.1, C-8 35.5, C-9 39.6, C-10 34.9, C-11 20.9, C-12 40.2, C-13 42.6, C-14 56.4, C-15 24.0, C-16 28.0, C-17 55.8, C-18 11.9, C-19 23.7, C-20 35.2, C-21 18.1, C-22 30.8, C-23 30.8, C-24 174.4, C-25 51.2(Ref. 0006)
Me ester (70eV) m/z: 390(M+1, 35%), 375(M-CH3, 18%), 372(M-H2O, 55%), 358(M-MeOH, 11%), 357(M-H2O-CH3, 35%), 248(M-SC-part of ring D (27), 27%), 233(M-SC-ring D (42), 62%), 230(M-H2O-SC-27, 11%), 217(M-173, 26%), 215(M-H2O-SC-42, 100%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Constituent of the bile of man, ox, rabbit, and hog.(Ref. 0001)
Identified in human of feces.(Ref. 0101/0161)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in feces of patients with cororectal cancer or polyps.(Ref. 0243)




[0001] / [0004] / [0005] / [0006] / [0007] / [0009] / [0010] / [0101] / [0161] / [0202] / [0243]
5
Allolithocholic Acid
3a-Hydroxy-5a-cholan-24-oic Acid
 BBA0005
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

204-208degC, (Me ester; mp, 160-161degC)(Ref. 0001/0237)
[a]d-26: +26.0deg, [a]d-26: +22.5pm1deg (C=0.85, CHCl3) (Me ester)(Ref. 0001/0237)
Me ester: nmaxcm-1: 3225, 1736, 1275, 1034, 1002, 956, 894(Ref. 0013)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.77(s), 21-Me 0.91(d), 3b-H 4.00(m)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.1, C-2 28.9, C-3 66.3, C-4 35.8, C-5 39.0, C-6 28.5, C-7 31.9, C-8 35.4, C-9 54.2, C-10 35.9, C-11 20.7, C-12 39.9, C-13 42.5, C-14 56.4, C-15 24.0, C-16 28.0, C-17 55.8, C-18 12.0, C-19 11.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.3(Ref. 0011)
Me ester (20eV) m/z: 390(M+1, 61%), 375(M-CH3, 16%), 372(M-H2O, 85%), 357(M-H2O-CH3, 27%), 249(M-141, 14%), 248(M-SC-part of ring D (27), 57%), 233(M-SC-ring D (42), 90%), 230(M-H2O-SC-27, 15%), 217(M-173, 40%), 215(M-H2O-SC-42, 100%)(Ref. 0012)


Isolated from human faceces.(Ref. 0001)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Isolated from urine of infants with biliary atresia.(Ref. 0185)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Constituent of a urinary bile acid in late prenancy and in recurrent cholestasis of pregnancy.(Ref. 0206)




[0001] / [0008] / [0011] / [0012] / [0013] / [0150] / [0151] / [0185] / [0191] / [0206] / [0237]
6
3b-Hydroxy-5a-cholan-24-oic Acid
 BBA0006
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

208-211degC(Ref. 0042/0237)
164-165degC (Me ester)(Ref. 0001/0002/0237)
[a]D: +33.3deg (C=0.12, EtOH)(Ref. 0042/0237)
[a]d-22: +21deg (CHCl3) (Me ester)(Ref. 0001/0002/0237)
nmaxcm-1: 1705 (C=O)(Ref. 0042)
Me ester: nmaxcm-1: 3494, 1712, 1297, 1051, 1002, 952, 893(Ref. 0013)
1H-NMR (CDCl3-CH3OH) d: 18-Me 0.69 (s), 19-Me 0.81 (s), 21-Me 0.95 (d), 3a-H 3.20-3.75 (m)(Ref. 0042)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.80(s), 21-Me 0.91(d), 3a-H 3.57(brm)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.9, C-2 31.3, C-3 71.0, C-4 38.0, C-5 44.7, C-6 28.6, C-7 31.9, C-8 35.4, C-9 54.2, C-10 35.2, C-11 21.1, C-12 39.9, C-13 42.5, C-14 56.3, C-15 24.0, C-16 27.9, C-17 55.8, C-18 11.9, C-19 12.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.2(Ref. 0011)
Me ester (70eV) m/z: 390(M+1, 56%), 375(M-CH3, 27%), 372(M-H2O, 40%), 357(M-H2O-CH3, 37%), 341(M-H2O-31, 16%), 257(M-H2O-SC, 6%),248(M-SC-part of ring D (27), 37%), 233(M-SC-ring D (42), 100%), 230(M-H2O-SC-27, 17%), 215(M-H2O-SC-42, 99%), 159(13%), 149(27%), 147(32%)(Ref. 0009/0012)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from the marine invertebrate Ptilosarcus gurneyi (sea pen).(Ref. 0096)




[0001] / [0002] / [0007] / [0008] / [0009] / [0011] / [0012] / [0013] / [0042] / [0096] / [0237]
7
6a-Hydroxy-5b-cholan-24-oic Acid
 BBA0007
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

226-228degC(Ref. 0019)
[a]D: +10deg (C=0.9, dioxane)(Ref. 0001)
[a]D: +5deg (CHCl3) (Me ester)(Ref. 0043)
nmaxcm-1: 1703 (C=O), 3348, 1022, 992 (OH)(Ref. 0019)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.64(s), 19-Me 0.90(s), 21-Me 0.92(d), 6b-H 4.01(brm)(Ref. 0019)
Me ester (70eV) m/z: 390(M+1, 2%), 375(M-CH3, 1%), 372(M-H2O, 100%), 357(M-H2O-CH3, 36%), 341(M-H2O-31, 11%), 257(M-H2O-SC, 15%), 249(7%), 248(M-SC-part of ring D, 15%), 233(M-SC-ring D (42), 8%), 231(9%), 230(M-H2O-SC-27, 25%), 217(21%), 215(M-H2O-SC-42, 67%), 159(8%), 149(30%), 147(24%)(Ref. 0009)







[0001] / [0009] / [0019] / [0043]
8
6b-Hydroxy-5b-cholan-24-oic Acid
 BBA0008
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

221-222degC(Ref. 0074)
112-114degC (Me ester)(Ref. 0043)
[a]D: +52deg (C=0.4, CHCl3) (Me ester)(Ref. 0043)









[0043] / [0074]
9
6a-Hydroxy-5a-cholan-24-oic Acid
 BBA0009
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

246-248degC(Ref. 0019)
nmaxcm-1: 1711 (C=O), 3383, 1034, 1004 (OH)(Ref. 0019)
1H-NMR (CDCl3+40%DMSO-d6; 90MHz) d: 18-Me 0.64(s), 19-Me 0.76(s), 21-Me 0.90(d), 6b-H 3.30(brm)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.618(s), 19-Me 0.754(s), 21-Me 0.882(d, 7.0), 6b-H 3.345(ddd, J, 5.0, 11.0, 15.5), COOMe 3.630(s)(Ref. 0019)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 38.94, C-2 21.85, C-3 26.26, C-4 22.85, C-5 53.84, C-6 70.22, C-7 41.66, C-8 34.27, C-9 54.22, C-10 37.02, C-11 20.79, C-12 39.93, C-13 42.69, C-14 56.43, C-15 24.19, C-16 28.11, C-17 55.91, C-18 12.11, C-19 13.40, C-20 35.42, C-21 18.33, C-22 31.06, C-23 31.12, C-24 174.81, C-25 51.53(Ref. 0019)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0007] / [0019]
10
6b-Hydroxy-5a-cholan-24-oic Acid
 BBA0010
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

227-230degC, (Me ester; mp, 87-90degC)(Ref. 0019)
nmaxcm-1: 1708 (C=O), 3390, 1022, 1004 (OH)(Ref. 0019)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 21-Me 0.93(d), 19-Me 1.00(s), 6a-H 3.72(m)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.655(s), 21-Me 0.888(d, 6.5), 19-Me 0.974(s), COOMe 3.632(s), 6a-H 3.743(dd, J, 3.5, 6.5)(Ref. 0019)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 40.46, C-2 22.17, C-3 27.13, C-4 26.10, C-5 49.70, C-6 72.55, C-7 39.55, C-8 30.27, C-9 54.64, C-10 36.26, C-11 20.68, C-12 40.05, C-13 42.78, C-14 56.37, C-15 24.22, C-16 28.16, C-17 55.99, C-18 12.19, C-19 15.81, C-20 35.45, C-21 18.36, C-22 31.09, C-23 31.15, C-24 174.84, C-25 51.53(Ref. 0019)








[0019]
11
7a-Hydroxy-5b-cholan-24-oic Acid
 BBA0011
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

96-99degC(Ref. 0001)
80-81degC (Me ester)(Ref. 0040)
[a]d-22: +7deg (CHCl3)(Ref. 0001)
[a]d-20: +6pm2deg (C=1.5) (Me ester)(Ref. 0132)
nmaxm: 9.70, 9.91, 10.22, 10.59(Ref. 0003)
Me ester: nmaxcm-1: 1724 (C=O), 3584 (OH), 1106(Ref. 0040)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.91(s), COOMe 3.68(s), 7b-H 3.86(br)(Ref. 0040)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.4, C-2 21.1, C-3 27.5, C-4 30.2, C-5 43.7, C-6 35.5, C-7 68.1, C-8 39.2, C-9 32.6, C-10 35.0, C-11 20.3, C-12 39.4, C-13 42.3, C-14 50.1, C-15 23.3, C-16 27.8, C-17 55.5, C-18 11.4, C-19 23.3, C-20 35.0, C-21 17.9, C-22 30.6, C-23 30.6, C-24 174.1, C-25 51.0(Ref. 0006)
Me ester (70eV) m/z: 372(M-H2O, 100%), 358(M-MeOH, 10%), 357(M-H2O-CH3, 40%), 276(M-114, 16%), 257(M-H2O-SC, 70%), 230(M-H2O-SC-part of ring D (27), 31%), 217(M-173, 13%), 215(M-H2O-SC-ring D (42), 61%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0001] / [0003] / [0006] / [0007] / [0009] / [0010] / [0040] / [0132]
12
7b-Hydroxy-5b-cholan-24-oic Acid
 BBA0012
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

131-133.5degC, (Me ester; mp, 89.0-90.5degC)(Ref. 0026)
Me ester: nmaxcm-1: 1695 (C=O), 3401, 1015, 990 (OH)(Ref. 0026)
1H-NMR (CDCl3; 100MHz) d: 18-Me 0.68(s), 19-Me 0.93(s), 7a-H 3.58(brm)(Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.64(s), 19-Me 0.99(s), 7a-H 3.60(brm), COOMe 3.68(s)(Ref. 0026)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.4, C-2 21.0, C-3 26.7, C-4 28.4, C-5 44.0, C-6 37.1, C-7 71.2, C-8 43.6, C-9 39.1, C-10 34.7, C-11 20.9, C-12 40.1, C-13 43.6, C-14 55.7, C-15 26.9, C-16 27.9, C-17 54.8, C-18 12.0, C-19 24.1, C-20 35.1, C-21 18.2, C-22 30.8, C-23 30.8, C-24 174.3, C-25 51.2(Ref. 0006)
Me ester (70eV) m/z: 390(M+1, 16%), 372(M-H2O, 100%), 358(M-MeOH, 11%), 357(M-H2O-CH3, 34%), 276(M-114, 16%), 257(M-H2O-SC, 64%), 233(M-SC-ring D (42), 15%), 230(M-H2O-SC-part of ring D (27), 33%), 217(M-173, 45%), 215(M-H2O-SC-42, 37%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Detected as a trace component of human stool.(Ref. 0101)
Detected in human feces.(Ref. 0219)




[0006] / [0007] / [0009] / [0010] / [0026] / [0101] / [0219]
13
7a-Hydroxy-5a-cholan-24-oic Acid
 BBA0013
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

155-156degC, (Me ester; mp, 105-106degC)(Ref. 0038/0237)
[a]d-25: -1.0pm0.5deg (C=1.0, MeOH)(Ref. 0038/0237)
[a]d-25: +2deg (C=0.95, MeOH) (Me ester)(Ref. 0001/0237)
nmax cm-1: 3279, 1701, 1255, 1236, 1212, 1096, 1029, 1014, 993, 959, 888, 778(Ref. 0038)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.78(s), 21-Me 0.92(d), 7b-H 3.80(m)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 38.6, C-2 22.2, C-3 26.8, C-4 28.8, C-5 39.4, C-6 37.1, C-7 68.1, C-8 39.8, C-9 46.6, C-10 36.5, C-11 20.8, C-12 39.9, C-13 42.9, C-14 50.9, C-15 23.7, C-16 28.0, C-17 56.2, C-18 11.9, C-19 11.1, C-20 35.4, C-21 18.4, C-22 31.2, C-23 31.2, C-24 174.2, C-25 51.0(Ref. 0011)
Me ester (20eV) m/z: 390(M+1, 7%), 372(M-H2O, 100%), 357(M-H2O-CH3, 22%), 257(M-H2O-SC, 76%), 249(M-141, 11%), 248(M-SC-part of ring D (27), 28%), 233(M-SC-ring D (42), 30%), 230(M-H2O-SC-27, 69%), 217(M-173, 24%), 215(M-H2O-SC-42, 31%)(Ref. 0009/0012)







[0001] / [0008] / [0009] / [0011] / [0012] / [0038] / [0237]
14
7b-Hydroxy-5a-cholan-24-oic Acid
 BBA0014
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

90.5-91degC (Me ester)(Ref. 0041/0237)
Me ester: nmaxcm-1: 3356 (OH), 1742 (COOMe), 1166 (COOMe), 1072 (OH)(Ref. 0041)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.80(s), 21-Me 0.93(d), 7a-H 3.37(m)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 39.0, C-2 22.3, C-3 26.8, C-4 28.9, C-5 44.5, C-6 39.1, C-7 75.4, C-8 44.0, C-9 53.5, C-10 35.3, C-11 21.1, C-12 40.4, C-13 43.9, C-14 56.2, C-15 27.0, C-16 28.6, C-17 55.5, C-18 12.4, C-19 12.4, C-20 35.3, C-21 18.5, C-22 31.3, C-23 31.3, C-24 174.3, C-25 51.1(Ref. 0011)
Me ester (20eV) m/z: 390(M+1, 9%), 372(M-H2O, 100%), 358(M-MeOH, 14%), 357(M-H2O-CH3, 32%), 257(M-H2O-SC (115), 58%), 249(M-141, 11%), 248(M-SC-part of ring D (27), 27%), 233(M-SC-ring D (42), 21%), 230(M-H2O-SC-27, 29%), 217(M-173, 42%), 215(M-H2O-SC-42, 26%)(Ref. 0009/0012)







[0008] / [0009] / [0011] / [0012] / [0041] / [0237]
15
12a-Hydroxy-5b-cholan-24-oic Acid
 BBA0015
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

110-116degC(Ref. 0001)
120.7-122.7degC (Me ester)(Ref. 0040)
[a]d-12: +37.9deg (C=1.844, acetone)(Ref. 0001)
nmaxm: 9.65, 9.91, 10.6-10.7(Ref. 0003)
Me ester: nmaxcm-1: 1715 (C=O), 3559 (OH), 1205, 1174(Ref. 0040)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.93(s), 21-Me 0.96(d), 12b-H 3.91(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.2, C-2 21.0, C-3 26.7, C-4 27.2, C-5 43.5, C-6 26.9, C-7 26.0, C-8 35.8, C-9 33.4, C-10 34.6, C-11 28.5, C-12 72.8, C-13 46.2, C-14 48.0, C-15 23.5, C-16 27.2, C-17 49.6, C-18 12.5, C-19 23.7, C-20 34.9, C-21 16.9, C-22 30.7, C-23 30.7, C-24 174.2, C-25 51.1(Ref. 0006)
Me ester (70eV) m/z: 372(M-H2O, 7%), 257(M-H2O-SC, 100%), 215(M-H2O-SC-ring D (42), 7%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0001] / [0003] / [0005] / [0006] / [0007] / [0009] / [0010] / [0040]
16
12b-Hydroxy-5b-cholan-24-oic Acid
 BBA0016
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

90-95degC, (Me ester; mp, 118degC)(Ref. 0001)
[a]d-12: +43.5deg (C=1.844, MeOH)(Ref. 0001)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.70(s), 19-Me 0.91(s), 21-Me 1.00(d), 12a-H 3.3(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.2, C-2 22.3, C-3 21.0, C-4 26.8, C-5 27.2, C-6 26.9, C-7 25.9, C-8 34.4, C-9 39.1, C-10 35.0, C-11 29.3, C-12 79.1, C-13 47.6, C-14 54.4, C-15 23.4, C-16 23.8, C-17 57.2, C-18 7.7, C-19 23.8, C-20 32.4, C-21 20.7, C-22 31.9, C-23 30.9, C-24 174.3, C-25 51.1(Ref. 0006)
Me ester (70eV) m/z: 372(M-H2O, 7%), 257(M-H2O-SC, 100%), 215(M-H2O-SC-ring D (42), 5%)(Ref. 0010)







[0001] / [0005] / [0006] / [0010]
17
12a-Hydroxy-5a-cholan-24-oic Acid
 BBA0017
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

199degC, (Me ester; mp, 118-119degC)(Ref. 0013/0237)
[a]d-25: +42.1pm0.5deg (C=1.01, MeOH)(Ref. 0013/0237)
[a]D: +41.6deg (Me ester)(Ref. 0237)
nmax cm-1: 3378, 1712, 1093, 1030, 935, 884(Ref. 0013)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.77(s), 21-Me 0.97(d), 12b-H 3.97(m)(Ref. 0008)
Me ester 13C-NMR (CDCl3 ; 22.53MHz) d: C-1 38.3, C-2 21.9, C-3 26.6, C-4 28.8, C-5 46.8, C-6 28.8, C-7 31.6, C-8 35.5, C-9 47.5, C-10 35.6, C-11 28.4, C-12 72.9, C-13 46.2, C-14 48.1, C-15 23.4, C-16 27.2, C-17 47.0, C-18 12.5, C-19 11.8, C-20 34.9, C-21 17.1, C-22 30.9, C-23 30.7, C-24 174.5, C-25 51.1(Ref. 0011)
Me ester (20eV) m/z: 372(M-H2O, 8%), 257(M-H2O-SC, 100%), 233(M-SC-42, 5%), 217(M-173, 5%), 215(M-H2O-SC-ring D (42), 5%)(Ref. 0009/0012)







[0008] / [0009] / [0011] / [0012] / [0013] / [0237]
18
12b-Hydroxy-5a-cholan-24-oic Acid
 BBA0018
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

128-129.5degC, (Me ester; mp, 84-86degC and 101-102degC)(Ref. 0014)
nmax cm-1: 1700 (C=O), 3420, 1000 (OH)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.79(s), 21-Me 1.00(d), 12a-H 3.37(brm), COOMe 3.63(s)(Ref. 0008/0014)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 38.5, C-2 22.0, C-3 26.6, C-4 28.8, C-5 46.9, C-6 28.8, C-7 32.1, C-8 34.1, C-9 53.4, C-10 36.0, C-11 29.4, C-12 79.4, C-13 47.7, C-14 54.4, C-15 23.4, C-16 23.8, C-17 57.2, C-18 7.6, C-19 12.0, C-20 32.6, C-21 20.8, C-22 31.5, C-23 31.2, C-24 174.4, C-25 51.2(Ref. 0011/0014)
Me ester (70eV) m/z: 372(M-H2O, 15%), 357(M-H2O-CH3, 5%), 257(M-H2O-SC, 10%), 233(M-SC-ringD (42), 8%), 215(M-H2O-SC-42, 6%)(Ref. 0012/0014)







[0008] / [0011] / [0012] / [0014]
19
1a,3a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0019
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

148-150degC (Me ester)(Ref. 0044)
[a]D: +21deg (CHCl3)(Ref. 0044)
Me ester: nmaxcm-1: 1730 (C=O), 3500 (OH)(Ref. 0044)
Me ester 1H-NMR (CDCl3) d: 3b-H 3.15(d), 1b-H 3.3, COOMe 3.6(Ref. 0044)








[0044]
20
1b,3a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0020
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

274-278degC, (Me ester; mp, 203-205degC)(Ref. 0016)
[a]d-25: +47.5deg (C=0.80, CHCl3) (Me ester)(Ref. 0016)
nmaxcm-1: 3300, 3200, 1680(Ref. 0016)
1H-NMR (Pyridin-d5; 90MHz) d: 18-Me 0.62(s), 19-Me 1.28(s), 1a-H 4.12-4.28(m), 3b-H 4.61-4.99(m)(Ref. 0016)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 1.04(s), COOMe 3.65(s), 1a-H 3.90(t, J, 3.0), 3b-H 3.83-4.17(m)(Ref. 0016)
Me-TMS ether (70eV) m/z: 535(M-15), 460(M-TMSOH, 10%), 370(M-2TMSOH, 3%), 217 (100%), 147(5%) (Ref. 0016)


A metabolite of lithocholic acid in human fetal liver.(Ref. 0164)
Detected in serum and urine from healthy human adults.(Ref. 0189)
Excreted in urine of healthy newborn.(Ref. 0194)




[0016] / [0164] / [0189] / [0194]
21
2b,3a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0021
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

193-196degC, (Me ester; mp, 164-166degC)(Ref. 0015)
nmaxcm-1: 1715 (C=O), 3364, 1001 (OH)(Ref. 0015)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.64(s), 19-Me 0.94(s), 2a- and 3b-H 3.33(brm)(Ref. 0015)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.64(s), 19-Me 0.96(s), 21-Me 0.91(d), COOMe 3.66(s), 2a-H 3.52(brm), 3b-H 3.42(brm)(Ref. 0015)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 43.27, C-2 71.53, C-3 76.85, C-4 34.18, C-5 42.10, C-6 26.50, C-7 26.41, C-8 35.90, C-9 42.07, C-10 37.23, C-11 21.12, C-12 40.13, C-13 42.76, C-14 56.44, C-15 24.21, C-16 28.23, C-17 55.99, C-18 12.10, C-19 23.41, C-20 35.43, C-21 18.33, C-22 31.14, C-23 31.04, C-24 174.88, C-25 51.58(Ref. 0015)
Me-TMS ether (20eV) m/z: 550(M+), 460(M-90), 406, 371 (M-90-89, 100%), 330(Ref. 0015)


Metabolite of lithocholic acid in human fetal liver; : stereochemistry of a hydroxyl groups at C-2 is unidentified.(Ref. 0164)




[0015] / [0164]
22
3a,4b-Dihydroxy-5b--cholan-24-oic Acid
 BBA0022
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

156-158degC, (Me ester; mp, 174-175degC)(Ref. 0017)
nmaxcm-1: 1703(C=O), 3456, 1019(OH)(Ref. 0017)
1H-NMR (CDCl3 ; 90MHz) d: 18-Me 0.65(s), 21-Me 0.93(d), 19-Me 0.96(s), 3b-H 3.41(brm), 4a-H 3.68(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.62(s), 19-Me 0.94(s), 21-Me 0.88(d), COOMe 3.64(s), 3b-H 3.38(brm), 4a-H 3.70(dd, J, 10.7, 9.1)(Ref. 0017)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.6, C-2 27.3, C-3 76.7, C-4 72.7, C-5 48.7, C-6 20.9, C-7 26.0, C-8 35.7, C-9 42.4, C-10 37.0, C-11 20.9, C-12 40.1, C-13 42.7, C-14 56.5, C-15 24.1, C-16 28.1, C-17 56.0, C-18 12.0, C-19 23.5, C-20 35.3, C-21 18.2, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.3(Ref. 0017)
Me ester (60eV) m/z: 406(M+ 16%), 388 (M-H2O, 100%), 370(M-2H2O, 23%), 264(M-SC-part of ring D (27), 18%), 249(M-SC-ring D (42), 21%), 231(M-SC-42-H2O, 24%), 213(M-SC-42-2H2O, 30%)(Ref. 0017)


Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Isolated from human fetal gallbladder bile.(Ref. 0198)




[0017] / [0188] / [0192] / [0198]
23
3b,4b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0023
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

189-191degC, (Me ester; mp, 131-133degC)(Ref. 0017)
nmaxcm-1: 1708 (C=O), 3412, 1028 (OH)(Ref. 0017)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 21-Me 0.92(d), 19-Me 0.96(s), 4a-H 3.71(brm), 3a-H 3.93(m)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.63(s), 19-Me 0.96(s), 21-Me 0.88(d), COOMe 3.64(s), 3a-H 3.99(m), 4a-H 3.86(dd, J, 11.3, 3.0)(Ref. 0017)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.2, C-2 25.8, C-3 68.4, C-4 69.5, C-5 44.0, C-6 21.1, C-7 26.0, C-8 35.5, C-9 41.6, C-10 36.6, C-11 20.7, C-12 40.1, C-13 42.6, C-14 56.6, C-15 24.1, C-16 28.1, C-17 56.0, C-18 12.0, C-19 23.6, C-20 35.3, C-21 18.2, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0017)
Me ester (60eV) m/z: 406(M+, 76%), 388 (M-H2O, 100%), 370(M-2H2O, 26%), 264(M-SC-part of ring D (27), 60%), 249(M-SC-ring D (42), 33%), 231(M-SC-42-H2O, 59%), 213(M-SC-42-2H2O, 39%)(Ref. 0017)







[0017]
24
Hyodeoxycholic Acid
3a,6a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0024
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

197-198degC(Ref. 0045)
[a]D: +8deg (MeOH)(Ref. 0045)
nmaxm: 9.72(Ref. 0003)
Me ester: nmaxm: 9.73(Ref. 0003)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.5, C-2 30.2, C-3 71.5, C-4 29.2, C-5 48.4, C-6 67.9, C-7 34.8, C-8 34.8, C-9 39.8, C-10 35.9, C-11 20.7, C-12 39.8, C-13 42.8, C-14 56.61, C-15 24.1, C-16 28.0, C-17 55.9, C-18 11.9, C-19 23.4, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0018)
Me ester (70eV) m/z: 406(M+1, 1%), 388(M-H2O, 100%), 373(M-H2O-CH3, 29%), 370(M-H2O, 96%), 357(M-H2O-31, 8%), 355(M-2H2O-CH3, 27%), 273(M-H2O-SC, 23%), 255(M-2H2O-SC, 61%), 249(M-SC-ring D (42), 11%), 246(M-H2O-SC-part of ring D (27), 31%), 228(M-2H2O-SC-27, 29%), 213(M-2H2O-SC-42, 80%)(Ref. 0009)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from pig bile.(Ref. 0001)
Occurred in plasma, liver, bile, and feces of rat.(Ref. 0101)
Bacterial 7-dehydroxylation product of hyodeoxycholic acid; a hepatic hydroxylation product of 7-oxolithocholic acid.(Ref. 0102)
Identified in urine of a patients with malabsorption.(Ref. 0143)
Identified in human meconium.(Ref. 0148)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Metabolite of lithocholic acid in human fetal liver.(Ref. 0164)
Detected in the bile of germ-free domestic fowl.(Ref. 0169)
Isolated from human fetal gallbladder bile.(Ref. 0198)
Identified in the serum and urine in cholestasis.(Ref. 0203)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)




[0001] / [0003] / [0007] / [0009] / [0018] / [0045] / [0101] / [0102] / [0143] / [0148] / [0150] / [0151] / [0164] / [0169] / [0198] / [0203] / [0206]
25
Murideoxycholic Acid
3a,6b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0025
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

214-215degC, (Me ester; mp, 114-115degC)(Ref. 0018)
[a]D: +37deg (MeOH)(Ref. 0216)
nmax cm-1: 1715 (C=O), 3410, 3300, 1050, 1028 (OH)(Ref. 0018)
1H-NMR (CDCl3+30%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 21-Me 0.93(d), 19-Me 1.11(s), 3b-H 3.57(brm), 6a-H 3.74(m)(Ref. 0018)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 21-Me 0.92(d), 19-Me 1.11(s), 3b-H 3.56(brm), COOMe 3.66(s) 6a-H 3.75(m)(Ref. 0018)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.8, C-2 30.1, C-3 71.2, C-4 36.5, C-5 48.6, C-6 73.1, C-7 34.7, C-8 30.7, C-9 40.7, C-10 34.3, C-11 20.6, C-12 40.0, C-13 42.7, C-14 56.3, C-15 24.2, C-16 28.1, C-17 56.0, C-18 12.0, C-19 25.5, C-20 35.3, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0018)
Me ester (70eV) m/z: 388 (M-H2O, 66%), 370(M-2H2O, 33%), 355(M-2H2O-CH3, 20%), 273(M-H2O-SC, 17%)(Ref. 0018)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


A trace component in the bile of pig bladders.(Ref. 0101)
Hepatic hydroxylation product of 7-oxolithocholic acid.(Ref. 0102)
Identified in urine of a patients with malabsorption.(Ref. 0143)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)




[0007] / [0018] / [0101] / [0102] / [0143] / [0150] / [0151] / [0202] / [0206] / [0216]
26
3b,6a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0026
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

198-199degC, (Me ester; mp, 74-75degC)(Ref. 0018)
nmax cm-1: 1702 (C=O), 3398, 1040 (OH)(Ref. 0018)
1H-NMR (CDCl3+30%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 21-Me 0.92(d), 19-Me 0.93(s), 6b-H 3.99(brm), 3a-H 4.09(m)(Ref. 0018)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 21-Me 0.91(d), 19-Me 0.94(s), 6b-H 4.10(brm), 3a-H 4.16(m)(Ref. 0018)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 30.0, C-2 27.5, C-3 66.0, C-4 26.3, C-5 43.0, C-6 67.8, C-7 34.6, C-8 34.6, C-9 39.1, C-10 36.4, C-11 21.0, C-12 40.0, C-13 42.9, C-14 56.2, C-15 24.1, C-16 28.0, C-17 56.0, C-18 12.0, C-19 23.9, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0018)
Me ester (70eV) m/z: 406(M+, 3%), 388 (M-H2O, 78%), 373(M-H2O-CH3, 24%), 370(M-2H2O, 23%), 355(M-2H2O-CH3, 11%), 273(M-H2O-SC, 13%)(Ref. 0018)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from pig bile.(Ref. 0101)
Metabolite of lithocholic acid in human fetal liver.(Ref. 0164)
Isolated from pig gallstone.(Ref. 0238)




[0007] / [0018] / [0101] / [0164] / [0238]
27
3b,6b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0027
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

260-261degC, (Me ester; mp, 124-125degC)(Ref. 0018)
nmax cm-1: 1710 (C=O), 3440, 3400, 1448, 1038, 1018 (OH)(Ref. 0018)
1H-NMR (CDCl3+30%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 21-Me 0.92(d), 19-Me 1.13(s), 6a-H 3.64(m), 3a-H 4.02(m)(Ref. 0018)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 21-Me 0.92(d), 19-Me 1.14(s), COOMe 3.66(S), 6a-H 3.71(m), 3a-H 4.09(m)(Ref. 0018)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 30.2, C-2 27.5, C-3 66.1, C-4 33.7, C-5 43.6, C-6 73.2, C-7 34.5, C-8 30.6, C-9 40.1, C-10 34.8, C-11 20.9, C-12 40.1, C-13 42.8, C-14 56.5, C-15 24.1, C-16 28.1, C-17 56.1, C-18 12.1, C-19 26.1, C-20 35.4, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.7, C-25 51.4(Ref. 0018)
Me ester (70eV) m/z: 406(M+, 2%), 388 (M-H2O, 94%), 373(M-H2O, 20%), 370(M-2H2O, 15%), 355(M-2H2O-CH3, 11%), 273(M-H2O-SC, 14%)(Ref. 0018)







[0018]
28
Allohyodeoxycholic Acid
3a,6a-Dihydroxy-5a-cholan-24-oic Acid
 BBA0028
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

238-240degC, (Me ester; mp, 176-177degC)(Ref. 0019/0237)
nmaxcm-1: 1704 (C=O), 3468, 1041, 1002 (OH)(Ref. 0019)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.77(s), 21-Me 0.92(d), 6b-H 3.29(brm), 3b-H 4.05(m)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.621(s), 19-Me 0.752(s), 21-Me 0.885(d, 6.5), 6b-H 3.323(dd,4.5, 10.5, 14.5), COOMe 3.630(s), 3b-H 4.092(brs)(Ref. 0019)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 32.53, C-2 28.48, C-3 65.97, C-4 30.10, C-5 46.15, C-6 69.82, C-7 41.98, C-8 34.30, C-9 53.82, C-10 36.93, C-11 20.74, C-12 39.88, C-13 42.69, C-14 56.32, C-15 24.22, C-16 28.11, C-17 55.96, C-18 12.11, C-19 12.37, C-20 35.44, C-21 18.33, C-22 31.06, C-23 31.16, C-24 174.80, C-25 51.55(Ref. 0019)








[0019] / [0237]
29
3a,6b-Dihydroxy-5a-cholan-24-oic Acid
 BBA0029
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

256-259degC, (Me ester; mp, 168-171degC)(Ref. 0019/0237)
[a]d-21: +9.36deg (C=1.0, CHCl3+n-propqnol)(Ref. 0046/0237)
nmaxcm-1: 1703 (C=O), 3435, 1026, 1009 (OH)(Ref. 0019)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 21-Me 0.93(d), 19-Me 0.98(s), 6a-H 3.65(m), 3b-H 4.05(m)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.656(s), 21-Me 0.886(d, 6.5), 19-Me 0.966(s), COOMe 3.628(s), 6a-H 3.707(dd,2.5, 5.0), 3b-H 4.136(brs)(Ref. 0019)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 34.03, C-2 29.16, C-3 66.71, C-4 33.15, C-5 41.76, C-6 72.28, C-7 39.78, C-8 30.37, C-9 54.22, C-10 36.15, C-11 20.67, C-12 39.97, C-13 42.78, C-14 56.26, C-15 24.23, C-16 28.14, C-17 55.94, C-18 12.19, C-19 14.92, C-20 35.45, C-21 18.35, C-22 31.07, C-23 31.15, C-24 174.88, C-25 51.56(Ref. 0019)








[0019] / [0046] / [0237]
30
3b,6a-Dihydroxy-5a-cholan-24-oic Acid
 BBA0030
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

247-249degC(Ref. 0019/0237)
180-182degC(Me ester)(Ref. 0019)
[a]D: +35deg(Ref. 0237)
nmaxcm-1: 1708 (C=O), 3378, 1043, 1009 (OH)(Ref. 0019)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.79(s), 21-Me 0.92(d), 3a- and 6b-H 3.45(brm)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.618(s), 19-Me 0.779(s), 21-Me 0.878(d, 6.0), 6b-H 3.373(ddd,4.0, 11.0, 15.0), 3a-H 3.537(m), COOMe 3.628(s)(Ref. 0019)
as Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 37.37, C-2 31.12, C-3 71.28, C-4 32.33, C-5 51.74, C-6 69.50, C-7 41.66, C-8 34.36, C-9 53.81, C-10 36.35, C-11 21.21, C-12 39.85, C-13 42.70, C-14 56.22, C-15 24.23, C-16 28.11, C-17 55.91, C-18 12.11, C-19 13.52, C-20 35.41, C-21 18.32, C-22 31.03, C-23 31.12, C-24 174.83, C-25 51.56(Ref. 0019)








[0019] / [0237]
31
3b,6b-Dihydroxy-5a-cholan-24-oic Acid
 BBA0031
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

286-289degC(Ref. 0019/0237)189-190degC (Me ester)(Ref. 0019/0237/0248)
nmaxcm-1: 1712 (C=O), 3409, 1039 (OH)(Ref. 0019)
1H-NMR (CDCl3+40%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 21-Me 0.91(d), 19-Me 0.98(s), 3a-H 3.45(brm), 6a-H 3.65(m)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.658(s), 21-Me 0.887(d, 6.0), 19-Me 0.998(s), 3a-H 3.603(m), COOMe 3.632(s), 6a-H 3.772(dd, 3.0, 6.0)(Ref. 0019)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 38.58, C-2 31.57, C-3 71.76, C-4 35.44, C-5 47.45, C-6 72.08, C-7 39.66, C-8 30.45, C-9 54.28, C-10 35.44, C-11 21.12, C-12 39.96, C-13 42.78, C-14 56.23, C-15 24.26, C-16 28.16, C-17 55.97, C-18 12.18, C-19 15.86, C-20 35.44, C-21 18.35, C-22 31.07, C-23 31.13, C-24 174.84, C-25 51.56(Ref. 0019)








[0019] / [0237] / [0248]
32
Chenodeoxycholic Acid
3a,7a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0032
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

167.5-172.5degC(Ref. 0020)
lmaxmm: 5.92 (C=O), 9.34, 10.25 (OH)(Ref. 0003/0020)
Me ester: nmaxmm: 9.33, 9.70, 9.87, 10.22(Ref. 0003)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.89(s), 21-Me 0.91(d), 3b-H 3.4(brm), 7b-H 3.79 (m)(Ref. 0005/0021)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.2, C-2 30.5, C-3 71.7, C-4 39.6, C-5 41.5, C-6 34.7, C-7 68.2, C-8 39.3, C-9 32.7, C-10 35.0, C-11 20.5, C-12 39.6, C-13 42.5, C-14 50.3, C-15 23.5, C-16 28.0, C-17 55.7, C-18 11.7, C-19 22.7, C-20 35.2, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0006)
Me ester (70eV) m/z: 388(M-H2O, 20%), 373(M-H2O-CH3, 11%), 370(M-2H2O, 100%), 355(M-2H2O-CH3, 61%), 273(M-H2O-SC, 57%), 264(M-SC-27, 22%), 255(M-2H2O-SC, 90%), 249(M-SC-ring D (42), 10%), 246(M-H2O-SC-part of ring D (27), 34%), 228(M-2H2O-SC-27, 57%), 213(M-2H2O-SC-42, 77%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Cholagogic agent used for dissolution of gallstones.(Ref. 0001/0101)
Simplest and common primary bile acid. Occurred in human bile and bile of many other vertebrates.(Ref. 0100/0101/0102)
Identified in urine and feces of healthy humans and patients with liver diseases.(Ref. 0150/0151/0161)
Identified in plasma of patients with bacterial overgrowth in the small intestine.(Ref. 0256)
Perpared from hyodeoxycholic acid.(Ref. 0084)
Perpared from androstenedione.(Ref. 0262)



[0001] / [0003] / [0005] / [0006] / [0007] / [0009] / [0010] / [0020] / [0021] / [0084] / [0100] / [0101] / [0102] / [0150] / [0151] / [0161] / [0256] / [0262]
33
Ursodeoxycholic Acid
3a,7b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0033
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

203.4-205.0degC, (Me ester; mp, 159-161degC)(Ref. 0022)
[a]d-30: +44.5deg (C=2.0, EtOH)(Ref. 0001)
nmax cm-1: 1709 (C=O), 1050, 1010 (OH)(Ref. 0022)
Me ester 1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 0.69(s), 19-Me 0.96(s), 3b- and 7a-H 3.55(brm), COOMe 3.65(s)(Ref. 0005/0021)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.8, C-2 30.1, C-3 70.9, C-4 37.2, C-5 42.4, C-6 37.0, C-7 70.9, C-8 43.4, C-9 39.2, C-10 33.9, C-11 21.1, C-12 40,1, C-13 43.6, C-14 55.8, C-15 26.8, C-16 28.4, C-17 54.9, C-18 12.0, C-19 23.3, C-20 35.1, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0006)
Me ester (70eV) m/z: 388(M-H2O, 58%), 370(M-2H2O, 94%), 355(M-2H2O-CH3, 44%), 273(M-H2O-SC, 28%), 264(M-SC-part of ring D (27), 14%), 255(M-2H2O-SC, 100%), 249(M-SC-ring D (42), 14%), 246(M-H2O-SC-27, 44%), 228(M-2H2O-SC-27, 33%), 213(M-2H2O-SC-42, 61%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 535(M-CH3, 3%), 460(M-TMSOH, 100%), 370(M-2TMSOH, 63%), 355(38%), 255(47%), 73(31%)(Ref. 0007/0049)


Occurred in bear bile.(Ref. 0001/0101)Cholagogic agent used for dissolution of gallstones.(Ref. 0001/0101)
Primary bile acid in bear and nutria.(Ref. 0100/0102)
Identified in urine and feces of healthy humans and patients with liver diseases.(Ref. 0150/0151/0161)
Identified in plasma of patients with bacterial overgrowth in the small intestine.(Ref. 0256)




[0001] / [0005] / [0006] / [0007] / [0010] / [0021] / [0022] / [0049] / [0100] / [0101] / [0102] / [0150] / [0151] / [0161] / [0256]
34
Isochenodeoxycholic Acid
3b,7a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0034
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

204.0-206.0degC, (Me ester; mp, 156.5-158.5degC)(Ref. 0021)
[a]D: +7deg (MeOH)(Ref. 0073)
nmax cm-1: 1715 (C=O), 1071, 1034, 1003, 982 (OH)(Ref. 0021)
Me ester 1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 0.67(s), 19-Me 0.94(s),7b-H 3.87(m), 3a-H 4.07(m)(Ref. 0005/0021)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.8, C-2 27.7, C-3 66.7, C-4 36.6, C-5 35.9, C-6 35.5, C-7 68.5, C-8 39.3, C-9 32.0, C-10 34.2, C-11 20.8, C-12 39.6, C-13 42.6, C-14 50.4, C-15 23.6, C-16 28.0, C-17 55.7, C-18 11.7, C-19 23.1, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.4(Ref. 0006)
Me ester (70eV) m/z: 388(M-H2O, 100%), 373(M-H2O-CH3, 37%), 370(M-2H2O, 31%), 357(M-H2O-CH3, 13%), 355(M-2H2O-CH3, 25%), 273(M-H2O-SC, 100%), 264(M-SC-part of ring D (27), 27%), 255(M-2H2O-SC, 23%), 249(M-SC-ring D (42), 30%), 246(M-H2O-SC-27, 55%), 228(M-2H2O-SC-27, 30%), 213(M-2H2O-SC-42, 61%)(Ref. 0009/0010)
Me-TMS ether (70eV) m/z: 460(M-TMSOH, 0.2%), 370(M-2TMSOH, 100%), 355(24%), 255(21%), 73(13%)(Ref. 0007/0049)


Detected as a trace component of human feces.(Ref. 0101/0161)
Identified in urine and serum of healthy humans and patients with liver diseases.(Ref. 0150/0151/0203/0212)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Identified in plasma of patients with bacterial overgrowth in the small intestine.(Ref. 0256)




[0005] / [0006] / [0007] / [0009] / [0010] / [0021] / [0049] / [0073] / [0101] / [0150] / [0151] / [0155] / [0161] / [0191] / [0203] / [0206] / [0212] / [0256]
35
Isoursodeoxycholic Acid
3b,7b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0035
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

166.0-168.5degC, (Me ester; mp, 124.0-125.0degC)(Ref. 0021)
[a]D: +56deg (MeOH)(Ref. 0073)
nmax cm-1: 1709 (C=O), 1031, 1061 (OH)(Ref. 0021)
1H-NMR (CDCl3; 100MHz) d: 18-Me 0.71(s), 19-Me 1.00(s), 7a-H 3.65(brm), 3a-H 4.07(m)(Ref. 0005/0021)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.71(s), 19-Me 1.00(s), 7a-H 3.55(brm), COOMe 3.65(s), 3a-H 4.04(m)(Ref. 0021)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.3, C-2 27.2, C-3 65.7, C-4 34.1, C-5 36.7, C-6 36.5, C-7 70.7, C-8 43.0, C-9 38.2, C-10 34.1, C-11 21.1, C-12 39.8, C-13 43.2, C-14 55.6, C-15 26.5, C-16 28.2, C-17 54.5, C-18 11.7, C-19 23.5, C-20 34.8, C-21 18.0, C-22 30.6, C-23 30.6, C-24 174.2, C-25 51.0(Ref. 0006)
Me ester (70eV) m/z: 388(M-H2O, 100%), 373(M-H2O-CH3, 41%), 370(M-2H2O, 34%), 357(M-H2O-CH3O, 13%), 355(M-2H2O-CH3, 24%), 273(M-H2O-SC, 9%), 264(M-SC-part of ring D (27), 27%), 255(M-2H2O-SC, 40%), 249(M-SC-ring D (42), 25%), 246(M-H2O-SC-27, 38%), 228(M-2H2O-SC-27, 17%), 213(M-2H2O-SC-42, 57%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 535(M-CH3, 1%), 460(M-TMSOH, 37%), 370(M-2TMSOH, 100%), 355(42%), 255(27%), 73(32%)(Ref. 0007/0049)


Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in serum and urine from patients with primary biliary cirrhosis.(Ref. 0149/0184/0187)




[0005] / [0006] / [0007] / [0010] / [0021] / [0049] / [0073] / [0124] / [0149] / [0184] / [0187]
36
Allochenodeoxycholic Acid
3a,7a-Dihydroxy-5a-cholan-24-oic Acid
 BBA0036
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

245-246degC, (Me ester; mp, 125-127degC)(Ref. 0023/0024/0237)
[a]d-25: +6.38deg (C=1.0, MeOH)(Ref. 0001/0237)
[a]D: +6.4deg (Me ester)(Ref. 0237)
nmax cm-1: 1702 (C=O), 3402, 1030, 1003 (OH)(Ref. 0023/0024)
1H-NMR (CDCl3+20%DMSO; 90MHz) d: 18-Me 0.65(s), 19-Me 0.76(s), 21-Me 0.92(d), 7b-H 3.75(m), 3b-H 3.97(m)(Ref. 0023/0024)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.78(s), 21-Me 0.92(d), COOMe 3.66(s), 7b-H 3.83(m), 3b-H 4.05(m)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.2, C-2 29.1, C-3 66.4, C-4 35.9, C-5 31.8, C-6 36.6, C-7 68.0, C-8 39.8, C-9 46.2, C-10 36.4, C-11 20.7, C-12 39.9, C-13 42.9, C-14 50.8, C-15 23.6, C-16 28.0, C-17 56.2, C-18 11.9, C-19 10.1, C-20 35.4, C-21 18.4, C-22 31.2, C-23 31.2, C-24 174.3, C-25 51.1(Ref. 0011)
Me ester (70eV) m/z: 406(M+, 3%), 388(M-H2O, 73%), 373(M-H2O-CH3, 17%), 370(M-2H2O, 19%), 355(M-2H2O-CH3, 12%), 273(M-H2O-SC, 66%), 264(M-SC-part of ring D (27), 29%), 249(M-SC-ring D (42), 32%), 246(M-H2O-SC-27, 37%), 228(M-2H2O-SC-27, 32%), 213(M-2H2O-SC-42, 40%)(Ref. 0009/0012/0023/0024)


A metabolite of 5a-cholestan-3b-ol in the hyperthyroid rat.(Ref. 0041)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Constituent of a urinary bile acid in late prenancy and in recurrent cholestasis of pregnancy.(Ref. 0206)




[0001] / [0008] / [0009] / [0011] / [0012] / [0023] / [0024] / [0041] / [0150] / [0151] / [0191] / [0206] / [0237]
37
Alloursodeoxycholic Acid
3a,7b-Dihydroxy-5a-cholan-24-oic Acid
 BBA0037
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

243.5-245degC(Ref. 0023/0237)
nmax cm-1: 1677(C=O), 3300, 1032, 1003 (OH)(Ref. 0023)
Me ester: nmax cm-1: 1735(C=O), 3430, 1032, 1003 (OH)(Ref. 0023)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.78(s), 21-Me 0.93(d), 7a-H 3.40(brm), 3b-H 3.95 (m)(Ref. 0023)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.79(s), 21-Me 0.93(d), 7a-H 3.34(brm), COOMe 3.65(s), 3b-H 4.05 (m)(Ref. 0008/0023)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.2, C-2 29.0, C-3 65.9, C-4 35.7, C-5 36.4, C-6 38.4, C-7 74.9, C-8 43.6, C-9 52.8, C-10 35.4, C-11 20.9, C-12 40,0, C-13 43.6, C-14 56.0, C-15 26.8, C-16 28.3, C-17 55.2, C-18 12.1, C-19 11.1, C-20 35.1, C-21 18.3, C-22 31.1, C-23 31.1, C-24 174.1, C-25 50.9(Ref. 0011)
Me ester (70eV) m/z: 388(M-H2O, 64%), 373(M-H2O-CH3, 14%), 370(M-2H2O, 100%), 355(M-2H2O-CH3, 36%), 255(M-2H2O-SC, 64%), 249(M-SC-ring D (42), 25%), 246(M-H2O-SC-part of ring D (27), 22%)(Ref. 0012/0023)







[0008] / [0011] / [0012] / [0023] / [0237]
38
3b,7a-Dihydroxy-5a-cholan-24-oic Acid
 BBA0038
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

271-272degC, (Me ester; mp, 106-161degC)(Ref. 0023)159-160degC (Me ester)(Ref. 0237)
[a]D: +14deg (Me ester)(Ref. 0237)
nmax cm-1: 1715 (C=O), 3550, 1042, 1024 (OH)(Ref. 0023)
Me ester: nmax cm-1: 1713(C=O), 3530, 1033, 1015 (OH)(Ref. 0023)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.78(s), 21-Me 0.92(d), 3a-H 3.53 (brm), 7b-H 3.74 (m)(Ref. 0023)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.80(s), 21-Me 0.92(d), 3a-H 3.58 (brm), COOMe 3.66(s), 7b-H 3.84 (m)(Ref. 0008/0023)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.8, C-2 31.1, C-3 70.8, C-4 37.5, C-5 36.6, C-6 36.3, C-7 67.5, C-8 39.3, C-9 45.6, C-10 35.3, C-11 20.8, C-12 39.3, C-13 42.4, C-14 50.2, C-15 23.4, C-16 27.8, C-17 55.6, C-18 11.6, C-19 11.0, C-20 35.1, C-21 18.0, C-22 30.8, C-23 30.8, C-24 174.4, C-25 51.1(Ref. 0011)
Me ester (70eV) m/z: 406(M+, 2%), 388(M-H2O, 100%), 373(M-H2O-CH3, 25%), 273(M-H2O-SC, 83%), 264(M-SC-part of ring D (27), 20%), 249(M-SC-ring D (42), 38%), 246(M-SC-H2O-27, 46%)(Ref. 0009/0012/0023)


Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)




[0008] / [0009] / [0011] / [0012] / [0023] / [0191] / [0237]
39
3b,7b-Dihydroxy-5a-cholan-24-oic Acid
 BBA0039
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

245-246.5degC, (Me ester; mp, 159-160degC)(Ref. 0023)
nmax cm-1: 1690(C=O), 3400, 1034(OH)(Ref. 0023)
Me ester: nmax cm-1: 1735 (C=O), 3340, 1037 (OH)(Ref. 0023)
1H-NMR (CDCl3+20%DMSO-d6 ; 90MHz) d: 18-Me 0.67(s), 19-Me 0.91(s), 21-Me 0.93(d), 3a- and 7a-H 3.35(brm)(Ref. 0023)
Me ester 1H-NMR (CDCl3; 90MHz) d : 18-Me 0.69(s), 19-Me 0.83(s), 21-Me 0.93(d), 3a- and 7a-H 3.41 (brm), COOMe 3.66(s)(Ref. 0008/0023)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.8, C-2 31.3, C-3 70.4, C-4 37.7, C-5 42.1, C-6 38.5, C-7 74.6, C-8 43.3, C-9 52.5, C-10 34.8, C-11 21.1, C-12 39.9, C-13 43.3, C-14 55.8, C-15 26.5, C-16 28.1, C-17 55.0, C-18 12.1, C-19 11.9, C-20 34.9, C-21 18.2, C-22 30.9, C-23 30.9, C-24 173.9, C-25 50.7(Ref. 0011)
Me ester (70eV) m/z: 406(M+, 2%), 388(M-H2O, 100%), 373(M-H2O-CH3, 35%), 273(M-H2O-SC, 62%), 264(M-SC-part of ring D (27), 20%), 255(M-H2O-SC, 27%), 249(M-SC-ring D (42), 29%), 246(M-H2O-SC-27, 35%)(Ref. 0012/0023)


Identified in human urine of patients with extra- or intrahepatic cholestasis.(Ref. 0187)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)




[0008] / [0011] / [0012] / [0023] / [0187] / [0191]
40
Deoxycholic Acid
3a,12a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0040
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

173.8-174.4degC, (Me ester; mp, 75.5-95.5degC)(Ref. 0025)
[a]D: +49.8deg (dioxane), +54.1deg (EtOH)(Ref. 0025)
[a]20.5D: +48deg (butanore) (Me ester)(Ref. 0001)
lmax mm: 5.80(COOH), 2.95, 9.65 (OH)(Ref. 0003/0025)
Me ester nmax m: 9.65, 9.87, 10.32, 10.56(Ref. 0003)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.91(s), 21-Me 0.96(d), 3b-H 3.5(brm),12b-H 3.93(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.1, C-2 30.2, C-3 71.4, C-4 36.2, C-5 42.0, C-6 27.1, C-7 26.0, C-8 35.9, C-9 33.3, C-10 33.9, C-11 28.5, C-12 72.8, C-13 46.3, C-14 47.9, C-15 23.6, C-16 27.4, C-17 47.0, C-18 12.5, C-19 22.9, C-20 35.1, C-21 17.1, C-22 31.0, C-23 30.8, C-24 174.5, C-25 51.2(Ref. 0006)
Me ester (70eV) m/z: 388(M-H2O, 4%), 370(M-2H2O, 21%), 273(M-H2O-SC, 72%), 255(M-2H2O-SC, 100%), 213(M-2H2O-SC-ring D (42), 13%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Common bile acid in many vertebrate.(Ref. 0100)
Occurred in bile of human, ox, rabbit, goat, sheep, and rat.(Ref. 0101)
Bacterial 7-dehydroxylation product of cholic acid.(Ref. 0102)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)




[0001] / [0003] / [0005] / [0006] / [0007] / [0009] / [0010] / [0025] / [0100] / [0101] / [0102] / [0150] / [0151]
41
Lagodeoxycholic Acid
Isodeoxycholic Acid
3a,12b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0041
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

172.5-173.6degC(Ref. 0025)
[a]D: +37.8deg (dioxane)(Ref. 0025)
lmax mm: 5.86(COOH), 2.82, 2.95, 9.65, 9.82, 10.00 (OH)(Ref. 0025)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 19-Me 0.86(s), 21-Me 0.95(d), 3b- and 12a-H 3.4(brm)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.2, C-2 30.3, C-3 71.1, C-4 35.9, C-5 41.6, C-6 26.9, C-7 25.8, C-8 34.4, C-9 39.3, C-10 34.2, C-11 29.5, C-12 79.1, C-13 47.8, C-14 54.8, C-15 23.5, C-16 24.0, C-17 57.3, C-18 7.8, C-19 23.0, C-20 32.5, C-21 20.7, C-22 32.0, C-23 31.2, C-24 174.6, C-25 51.2(Ref. 0006)
Me ether (70eV) m/z: 388(M-H2O, 8%), 370(M-2H2O, 13%), 273(M-H2O-SC, 92%), 255(M-2H2O-SC, 100%), 213(M-2H2O-SC-ring D (42), 9%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 538(M-CH3, 8%), 460(M-TMSOH, 4%), 370(M-2TMSOH, 25%), 355(13%), 255(100%), 73(17%)(Ref. 0007/0049)


Identified in human feces.(Ref. 0101/0161)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151/0212)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Excreted in duodenal bile and urine of diabetic patients.(Ref. 0221)
Identified in feces of patients with cororectal cancer or polyps.(Ref. 0243)
Constituent in the bile of rabbits and hamsters.(Ref. 0257)




[0005] / [0006] / [0007] / [0010] / [0025] / [0049] / [0101] / [0150] / [0151] / [0161] / [0206] / [0212] / [0221] / [0243] / [0257]
42
Isodeoxycholic Acid
3b,12a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0042
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

178.4-180.5degC, (Me ester; mp, 156.5-158.2degC)(Ref. 0025)
[a]D: +39.0deg (dioxane), +45.6deg (EtOH)(Ref. 0025)
lmax mm: 5.78, 5.85(COOH), 2.80, 2.92, 9.70 (OH)(Ref. 0025)
1H-NMR (DMSO-d6; 270MHz) d: 18-Me 0.60(s), 19-Me 0.86(s), 21-Me 0.91(d), 12b-H 3.78(t, J=2.8), 3a-H 3.88(J=3.0)(Ref. 0073)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.94(s), 21-Me 0.95(d), 12b-H 3.91(m), 3a-H 4.04(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.7, C-2 27.6, C-3 66.9, C-4 33.3, C-5 36.4, C-6 26.5, C-7 25.9, C-8 35.7, C-9 32.7, C-10 34.5, C-11 28.8, C-12 73.0, C-13 46.4, C-14 48.3, C-15 23.5, C-16 27.4, C-17 47.2, C-18 12.6, C-19 23.5, C-20 35.0, C-21 17.2, C-22 31.0, C-23 30.8, C-24 174.5, C-25 51.4(Ref. 0006)
Me ether (70eV) m/z: 388(M-H2O, 8%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 65%), 213(M-2H2O-SC-ring D (42), 7%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Detected as a trace component of rabbit and human feces.(Ref. 0101/0157/0161)
Identified in urine of healthy humans and patients with liver diseases(Ref. 0150/0151)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Excreted in duodenal bile and urine of diabetic patients.(Ref. 0221)




[0005] / [0006] / [0007] / [0009] / [0010] / [0025] / [0073] / [0101] / [0150] / [0151] / [0157] / [0161] / [0191] / [0206] / [0221]
43
3b,12b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0043
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

204.3-205.6degC, (Me ester; mp, 115.8-116.3degC)(Ref. 0025)
[a]D: +27.0deg (dioxane)(Ref. 0025)
lmax mm: 5.84 (COOH), 2.80, 3.00, 9.73, 9.95 (OH)(Ref. 0025)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 19-Me 0.96(s), 21-Me 1.00(d), 12a-H 3.4(brm), 3a-H 4.06(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.5, C-2 27.3, C-3 66.1, C-4 33.0, C-5 35.7, C-6 26.3, C-7 25.5, C-8 33.9, C-9 38.3, C-10 34.5, C-11 29.1, C-12 78.9, C-13 47.5, C-14 54.2, C-15 23.3, C-16 23.6, C-17 57.0, C-18 7.5, C-19 23.3, C-20 32.1, C-21 20.5, C-22 31.8, C-23 31.0, C-24 174.4, C-25 51.0(Ref. 0006)
Me ether (70eV) m/z: 388(M-H2O, 12%), 273(M-H2O-SC, 92%), 255(M-2H2O-SC, 100%), 213(M-2H2O-SC-ring D (42), 7%)(Ref. 0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Detected as a trace component of human feces.(Ref. 0101/0161)




[0005] / [0006] / [0007] / [0010] / [0025] / [0101] / [0161]
44
Allodeoxycholic Acid, b-Lagodeoxycholic Acid
3a,12a-Dihydroxy-5a-cholan-24-oic Acid
 BBA0044
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

220-221degC, (Me ester; mp, 179.0-180.5degC)(Ref. 0014/0237)
[a]d-27: +42pm1deg (C=0.75, 90%EtOH), [a]d-23: +35.6pm1deg (C=1.0, MeOH) (Me ester)(Ref. 0001/0237)
Me ester: nmaxcm-1: 1690 (C=O), 3350, 1060, 1013, 1003, 975, 955 (OH)(Ref. 0014)
1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.68(s), 19-Me 0.77(s), 21-Me 1.00(d), 3b- and 12b-H 3.95(m)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.79(s), 21-Me 0.98(d), COOMe 3.63(s), 3b- and 12b-H 3.96(m)(Ref. 0008/0014)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.1, C-2 28.8, C-3 66.2, C-4 35.7, C-5 38.9, C-6 28.4, C-7 32.1, C-8 34.1, C-9 53.0, C-10 35.8, C-11 29.4, C-12 79.3, C-13 47.7, C-14 54.4, C-15 23.4, C-16 23.8, C-17 57.2, C-18 7.8, C-19 11.0, C-20 32.6, C-21 20.8, C-22 31.4, C-23 31.1, C-24 174.5, C-25 51.3(Ref. 0011/0014)
Me ester (70eV) m/z: 388(M-H2O, 6%), 373(M-H2O-CH3, 2%), 357(M-H2O-CH3O, 4%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 40%), 249(M-SC-ring D (42), 2%), 213(M-2H2O-SC-42, 6%)(Ref. 0009/0012/0014)


Constituent of rabbit bile and faeces.(Ref. 0001/0101/0158)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
A major component of gallstones induced in the rabbit by 5-acholestan-3b-ol.(Ref. 0171)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)




[0001] / [0008] / [0009] / [0011] / [0012] / [0014] / [0101] / [0150] / [0151] / [0158] / [0171] / [0206] / [0237]
45
Allo-isodeoxycholic Acid
3a,12b-Dihydroxy-5a-cholan-24-oic Acid
 BBA0045
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

206.5-207.5degC, (Me ester; mp, 143-144degC)(Ref. 0014)
nmaxcm-1: 1680(C=O), 3440, 1050, 1028, 1013, 1000, 970(OH)(Ref. 0014)
1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.72(s), 19-Me 0.79(s), 21-Me 1.03(d), 12a-H 3.39(brm), 3b-H 3.99(m)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d : 18-Me 0.73(s), 19-Me 0.79(s), 21-Me 1.01(d), 12a-H 3.37(brm), COOMe 3.65(s), 3b-H 4.01(m)(Ref. 0008/0014)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.1, C-2 28.8, C-3 66.2, C-4 35.7, C-5 38.9, C-6 28.4, C-7 32.1, C-8 34.1, C-9 53.0, C-10 35.8, C-11 29.4, C-12 79.3, C-13 47.7, C-14 54.4, C-15 23.4, C-16 23.8, C-17 57.2, C-18 7.8, C-19 11.0, C-20 32.6, C-21 20.8, C-22 31.4, C-23 31.1, C-24 174.5, C-25 51.3(Ref. 0011/0014)
Me ester (70eV) m/z: 388(M-H2O, 9%), 357(M-H2O-CH3O, 5%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 57%), 249(M-SC-ring D (42), 7%), 213(M-2H2O-SC-42, 6%)(Ref. 0012/0014)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Identified in feces of patients with cororectal cancer or polyps.(Ref. 0243)




[0007] / [0008] / [0011] / [0012] / [0014] / [0243]
46
3b,12a-Dihydroxy-5a-cholan-24-oic Acid
 BBA0046
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

228.5-229.5degC, (Me ester; mp, 140-142degC)(Ref. 0014/0237)
[a]D: +38deg (MeOH)(Ref. 0001/0237)
[a]d-25: +35.2pm1deg (C=0.33, MeOH) (Me ester)(Ref. 0038/0237)
nmaxcm-1: 1715(C=O), 3530, 1042, 1017, 982, 958(OH)(Ref. 0014)
1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.68(s), 19-Me 0.80(s), 21-Me 1.00(d), 3a-H 3.52(brm), 12b-H 3.92(m)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.82(s), 21-Me 0.98(d), 3a-H 3.57(brm) COOMe 3.65(s) 12b-H 3.97(m)(Ref. 0008/0014)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.7, C-2 31.5, C-3 70.8, C-4 37.9, C-5 44.6, C-6 28.4, C-7 31.2, C-8 35.5, C-9 47.2, C-10 34.9, C-11 28.7, C-12 72.8, C-13 46.2, C-14 47.9, C-15 23.4, C-16 27.1, C-17 47.0, C-18 12.5, C-19 12.0, C-20 34.9, C-21 17.1, C-22 30.9, C-23 30.7, C-24 174.4, C-25 51.2(Ref. 0011/0014)
Me ester (70eV) m/z: 388(M-H2O, 5%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 28%), 249(M-SC-ring D (42), 4%), 213(M-2H2O-SC-42, 5%)(Ref. 0009/0012/0014)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)




[0001] / [0007] / [0008] / [0009] / [0011] / [0012] / [0014] / [0038] / [0150] / [0151] / [0206] / [0237]
47
3b,12b-Dihydroxy-5a-cholan-24-oic Acid
 BBA0047
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

223.5-225.5degC, (Me ester; mp, 139-140degC and 159-160degC)(Ref. 0014)
nmaxcm-1: 1715 (C=O), 3250, 1040, 1027, 975 (OH)(Ref. 0014)
1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.71(s), 19-Me 0.81(s), 21-Me 1.03(d), 3a- and 12a-H 3.38(brm)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 19-Me 0.81(s), 21-Me 1.01(d), 3a- and 12a-H 3.39(brm) COOMe 3.64(s)(Ref. 0008/0014)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.8, C-2 31.4, C-3 70.7, C-4 37.7, C-5 44.6, C-6 28.4, C-7 32.0, C-8 34.0, C-9 52.9, C-10 35.2, C-11 29.3, C-12 79.1, C-13 47.6, C-14 54.2, C-15 23.4, C-16 23.7, C-17 57.1, C-18 7.7, C-19 12.0, C-20 32.4, C-21 20.7, C-22 31.4, C-23 31.1, C-24 174.4, C-25 51.2(Ref. 0011/0014)
Me ester (70eV) m/z: 388(M-H2O, 9%), 373(M-H2O-CH3O, 5%), 357(M-H2O-CH3O, 5%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 25%), 249(M-SC-ring D (42), 5%)(Ref. 0012/0014)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0007] / [0008] / [0011] / [0012] / [0014]
48
3a,15b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0048
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

185.5-186.5degC(Ref. 0047)
[a]d-25: +3.4deg (C=1.0, EtOH)(Ref. 0047)
nmaxcm-1: 1700 (C=O), 3280 (OH)(Ref. 0047)
1H-NMR (C6D6+CD3OD; 300MHz) d: 21-Me 0.88(d), 18-Me 0.92(s), 19-Me 1.00(s), 3b-H 3.52(m), 15a-H 3.98(m)(Ref. 0047)
13C-NMR (CD3OD; 25MHz) d: C-1 37.3, C-2 32.3, C-3 72.7, C-4 42.1, C-5 43.6, C-6 28.3, C-7 26.8, C-8 36.4, C-9 42.2, C-10 35.9, C-11 21.8, C-12 42.9, C-13 43.6, C-14 62.4, C-15 70.6, C-16 31.2, C-17 61.5, C-18 15.2, C-19 24.0, C-20 33.0, C-21 18.9, C-22 36.6, C-23 31.9, C-24 178.0(Ref. 0047)
Molecular secondary ion mass spectrometry m/z: 415(M+Na)+, 485(M+H+glycerol)(Ref. 0047)


A microbiological hydroxylation product of litocholic acid by a Cunninghamella sp ST-22.(Ref. 0047/0182)




[0047] / [0182]
49
7a,12a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0049
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

204-206degC, (Me ester; mp, 155-156degC)(Ref. 0027)
[a]d-21: +81deg (dioxane), [a]d-21: +17deg (CHCl3) (Me ester)(Ref. 0001)
nmaxmm: 9.68, 9.72, 10.20, 10.53(Ref. 0003)
Me ester: nmax cm-1: 1724 (C=O), 3425, 1024, 984 (OH)(Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.68(s), 19-Me 0.89(s), COOMe 3.63(s), 7b- 3.84(m), 12b-H 3.96(m)(Ref. 0026)
13C-NMR (CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.2, C-3 27.7, C-4 30.4, C-5 43.1, C-6 35.4, C-7 68.7, C-8 39.5, C-9 26.3, C-10 35.6, C-11 28.1, C-12 73.1, C-13 46.5, C-14 41.5, C-15 23.2, C-16 27.4, C-17 47.1, C-18 12.4, C-19 23.2, C-20 35.3, C-21 17.2, C-22 31.1, C-23 30.8, C-24 174.6, C-25 51.3(Ref. 0006)
m/z: 374(M-H2O, 3.2%), 356(M-2H2O, 72.5%), 273(M-H2O-SC, 8.8%), 255(M-2H2O-SC, 100.0%)(Ref. 0027)
Me ester (70eV) m/z: 370(M-2H2O,36%), 355(M-2H2O-CH3, 11%), 255(M-2H2O-SC, 100%), 228(M-2H2O-SC-part of ring D (27), 11%), 213(M-2H2O-SC-ring D (42), 4%)(Ref. 0010)
Me ester-DMES ether m/z: 578(M+, 0.2%), 563(M-CH3, 3.1%), 549(M-29, 100.0%), 370(M-2DMESOH, 29.7%), 255(M-2DMESOH-SC, 33.7%)(Ref. 0009/0027)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0001] / [0003] / [0006] / [0007] / [0009] / [0010] / [0026] / [0027]
50
7a,12b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0050
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

150.0-152.5degC, (Me ester; mp, 129.5-131.0degC)(Ref. 0026)
nmax cm-1: 1701 (C=O), 3448, 1018, 1005, 992 (OH)(Ref. 0026)
1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 0.72(s), 19-Me 0.91(s), 12a- 3.51(brm), 7b-H 3.82(m)(Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.72(s), 19-Me 0.91(s), 12a- 3.47(brm), COOMe 3.64(s), 7b-H 3.84(m)(Ref. 0026)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.4, C-2 21.2, C-3 27.5, C-4 30.2, C-5 42.7, C-6 35.1, C-7 68.0, C-8 37.9, C-9 31.9, C-10 35.6, C-11 29.2, C-12 78.8, C-13 47.4, C-14 48.4, C-15 22.9, C-16 23.7, C-17 56.9, C-18 7.5, C-19 23.2, C-20 32.4, C-21 20.8, C-22 32.0, C-23 30.8, C-24 174.5, C-25 51.2(Ref. 0006)
m/z: 374(M-H2O, 1.3%), 356(M-2H2O, 32.4%), 273(M-H2O-SC, 23.5%), 255(M-2H2O-SC, 100.0%)(Ref. 0027)
Me ester (70eV) m/z: 370(M-2H2O, 16%), 273(M-H2O-SC, 15%), 255(M-2H2O-SC, 100%)(Ref. 0010)
Me ester-DMES ether m/z: 578(M+, 0.6%), 563(M-CH3, 2.9%), 549(M-29, 100.0%), 370(M-2DMESOH, 14.9%), 255(M-2DMESOH-SC, 26.7%)(Ref. 0027)







[0006] / [0010] / [0026] / [0027]
51
7b,12a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0051
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

174.5-176.0degC, (Me ester; mp, 131-132degC)(Ref. 0026)
nmax cm-1: 1689 (C=O), 3356, 1026, 1015, 943 (OH)(Ref. 0026)
1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 0.67(s), 19-Me 0.90(s), 7a- 3.49(brm), 12b-H 3.88(m)(Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d : 18-Me 0.70(s), 19-Me 0.93(s), 7a- 3.57(brm), COOMe 3.63(s), 12b-H 3.98(m)(Ref. 0026)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.2, C-2 20.7, C-3 26.8, C-4 27.8, C-5 43.9, C-6 36.8, C-7 71.1, C-8 43.7, C-9 31.9, C-10 34.1, C-11 28.7, C-12 72.2, C-13 47.1, C-14 47.2, C-15 26.2, C-16 27.6, C-17 45.7, C-18 12.6, C-19 23.8, C-20 34.8, C-21 17.1, C-22 30.8, C-23 30.8, C-24 174.4, C-25 51.2(Ref. 0006)
m/z: 374(M-H2O, 3.6%), 356(M-2H2O, 24.5%), 273(M-H2O-SC, 77.5%), 255(M-2H2O-SC, 100.0%)(Ref. 0027)
Me ester (70eV) m/z: 370(M-2H2O, 16%), 273(M-H2O-SC, 56%), 255(M-2H2O-SC, 100%)(Ref. 0010)
Me ester-DMES ether m/z: 578(M+, 0.2%), 563(M-CH3, 4.0%), 549(M-29, 100.0%), 370(M-2DMESOH, 34.7%), 255(M-2DMESOH-SC, 56.4%)(Ref. 0027)







[0006] / [0010] / [0026] / [0027]
52
7b,12b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0052
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

179-182degC, (Me ester; mp, 110-110.5degC)(Ref. 0026)
nmax cm-1: 1642 (C=O), 3413, 1026, 1015, 956 (OH)(Ref. 0026)
1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 0.72(s), 19-Me 0.93(s), 7a- and 12a-H 3.41(brm)(Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.76(s), 19-Me 0.96(s), 7a- and 12a-H 3.41(brm), COOMe 3.64(s)(Ref. 0026)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.1, C-3 26.9, C-4 28.0, C-5 43.8, C-6 37.1, C-7 71.2, C-8 42.3, C-9 37.8, C-10 34.7, C-11 29.0, C-12 79.4, C-13 48.6, C-14 53.9, C-15 26.2, C-16 23.6, C-17 56.5, C-18 8.0, C-19 24.0, C-20 32.3, C-21 21.1, C-22 32.3, C-23 31.2, C-24 174.6, C-25 51.4(Ref. 0006)
m/z: 374(M-H2O, 3.3%), 356(M-2H2O, 66.6%), 273(M-H2O-SC, 84.3%), 255(M-2H2O-SC, 100.0%)(Ref. 0027)
Me ester (70eV) m/z: 370(M-2H2O, 20%), 273(M-H2O-SC, 70%), 255(M-2H2O-SC, 100%)(Ref. 0010)
Me ester-DMES ether m/z: 578(M+, 0.2%), 563(M-CH3, 3.6%), 549(M-29, 100.0%), 370(M-2DMESOH, 19.8%), 255(M-2DMESOH-SC, 17.8%)(Ref. 0027)







[0006] / [0010] / [0026] / [0027]
53
7a,12a-Dihydroxy-5a-cholan-24-oic Acid
 BBA0053
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

236-237degC, (Me ester; mp, 170-172degC)(Ref. 0038/0237)
[a]d-25: +22.0pm0.50deg (C=1.0, MeOH), [a]d-25: +21.2deg (C=0.98, MeOH) (Me ester)(Ref. 0001/0237)
nmax cm-1: 1719(C=O), 3400, 1028(OH)(Ref. 0028)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.77(s), 21-Me 0.99(d), 7b-H 3.74(m), 12b-H 3.89(m)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.78(s), 21-Me 0.98(d), COOMe 3.66(s), 7b-H 3.81(m), 12b-H 3.96(m)(Ref. 0008/0028)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 38.2, C-2 22.0, C-3 26.6, C-4 28.6, C-5 39.1, C-6 36.8, C-7 67.9, C-8 39.7, C-9 39.7, C-10 35.9, C-11 28.3, C-12 72.8, C-13 17.3, C-14 42.3, C-15 23.0, C-16 27.3, C-17 47.2, C-18 12.5, C-19 10.9, C-20 35.1, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0011)
Me ester (70eV) m/z: 388(M-H2O, 7%), 370(M-2H2O, 73%), 355(M-2H2O-CH3, 16%), 273(M-H2O-SC, 15%), 255(M-2H2O-SC, 100%)(Ref. 0012/0028)







[0001] / [0008] / [0011] / [0012] / [0028] / [0038] / [0237]
54
7a,12b-Dihydroxy-5a-cholan-24-oic Acid
 BBA0054
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

168-170degC, (Me ester; mp, 147.5-148.0degC)(Ref. 0028)
nmax cm-1: 1708(C=O), 3425, 1032, 1015(OH)(Ref. 0028)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.77(s), 21-Me 1.02(d), 12a-H 3.27(brm), 7b-H 3.74(m)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 19-Me 0.79(s), 21-Me 1.01(d), 12a-H 3.39(brm), COOMe 3.66(s), 7b-H 3.83(m)(Ref. 0008/0028)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 38.3, C-2 21.9, C-3 26.5, C-4 28.4, C-5 39.1, C-6 36.8, C-7 67.6, C-8 38.2, C-9 45.2, C-10 36.2, C-11 29.5, C-12 78.9, C-13 47.6, C-14 48.7, C-15 23.0, C-16 23.9, C-17 57.2, C-18 7.6, C-19 10.9, C-20 32.7, C-21 20.9, C-22 32.1, C-23 31.0, C-24 174.6, C-25 51.3(Ref. 0011)
Me ester (70eV) m/z: 388(M-H2O, 5%), 370(M-2H2O, 18%), 355(M-2H2O-CH3O, 8%), 273(M-H2O-SC, 35%), 255(M-2H2O-SC, 100%)(Ref. 0012/0028)







[0008] / [0011] / [0012] / [0028]
55
7b,12a-Dihydroxy-5a-cholan-24-oic Acid
 BBA0055
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

207.5-208.5degC, (Me ester ; mp, 133.5-14.0degC)(Ref. 0028)
[a]D: +76.7deg (C=0.45, MeOH) (Me ester)(Ref. 0001)
nmax cm-1: 1685(C=O), 3300, 1028, 990(OH)(Ref. 0028)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.78(s), 21-Me 0,99(d), 7a-H 3.26(brm), 12b-H 3.90(m)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.80(s), 21-Me 0.99(d), 7a-H 3.38(brm), COOMe 3.66(s), 12b-H 3.98(brm)(Ref. 0008/0028)
13C-NMR (CDCl3; 22.53MHz) d: C-1 38.5, C-2 22.0, C-3 26.5, C-4 28.5, C-5 44.0, C-6 38.7, C-7 74.9, C-8 43.6, C-9 45.7, C-10 35.2, C-11 28.6, C-12 72.4, C-13 47.3, C-14 47.6, C-15 26.3, C-16 27.7, C-17 46.0, C-18 12.7, C-19 12.1, C-20 34.9, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.4, C-25 51.3(Ref. 0011)
Me ester (70eV) m/z: 388(M-H2O, 3%), 370(M-2H2O, 20%), 355(M-2H2O-CH3, 6%), 273(M-H2O-SC, 78%), 255(M-2H2O-SC, 100%)(Ref. 0009/0012/0028)







[0001] / [0008] / [0009] / [0011] / [0012] / [0028]
56
7b,12b-Dihydroxy-5a-cholan-24-oic Acid
 BBA0056
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

208-210degC, (Me ester; mp, 154.5-156.0degC)(Ref. 0028)
nmax cm-1: 1677(C=O), 3275, 1036, 1008, 990(OH)(Ref. 0028)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.72(s), 19-Me 0.80(s), 21-Me 1.00(d), 7a- and 12b-H 3.90(brm)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.76(s), 19-Me 0.81(s), 21-Me 1.00(d), 7a- and 12a-H 3.26(brm), COOMe 3.66(s)(Ref. 0008/0012)
13C-NMR (CDCl3; 22.53MHz) d: C-1 38.6, C-2 21.9, C-3 26.4, C-4 28.5, C-5 44.2, C-6 38.7, C-7 74.8, C-8 42.1, C-9 51.6, C-10 35.5, C-11 29.1, C-12 79.4, C-13 48.5, C-14 53.9, C-15 26.3, C-16 23.7, C-17 56.5, C-18 8.0, C-19 12.2, C-20 32.5, C-21 21.1, C-22 32.3, C-23 31.0, C-24 175.5, C-25 51.3(Ref. 0011)
Me ester (70eV) m/z: 388(M-H2O, 5%), 370(M-2H2O, 23%), 355(M-2H2O-CH3, 7%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 65%)(Ref. 0012/0028)







[0008] / [0011] / [0012] / [0028]
57
Vulpecholic Acid
1a,3a,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0057
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

150-152degC(Ref. 0039)
Me ester 1H-NMR (CDCl3; 90MHz) d: 0.76 (3H, s, 18-CH3), 0.90 (3H, bd, 21-CH3), 1.11 (3H, s, 19-CH3), 2.5-3.5 (br), 3.30 (bd), 3.68 (S, COOMe), 3.85 (bs)(Ref. 0039)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 79.21, C-2 40.08, C-3 67.99, C-4 39.20, C-5 39.20, C-6 34.15, C-7 69.08, C-8 40.57, C-9 34.69, C-10 39.65, C-11 23.10, C-12 40.08, C-13 42.25, C-14 50.22, C-15 24.00, C-16 27.90, C-17 56.20, C-18 11.74, C-19 18.73, C-20 35.37, C-21 18.29, C-22 22.98, C-23 30.98, C-24 174.88, C-25 51.52(Ref. 0039)
(15eV) m/z: 408 (M+, 6%), 390(M-18, 99%), 372(M-2H2O, 100%), 368(M-2H2O-4H, 40%), 357(M-2H2O-CH3, 14%), 354 (M-3H2O, 15%), 302(RDA-ion, 36%), 300 (10%), 289 (M-H2O-SC, 11%), 280(M-SC-C-16,17, 10%), 244(M-2H2O-SC-C-16,17, 10%)(Ref. 0039)


Isolated from the gallbladaer bile of the Australian opossum, Trichosurus vulpecula (Lesson).(Ref. 0039)
Primary bile acid in Australian marsupials.(Ref. 0102)




[0039] / [0102]
58
1b,3a,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0058
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

266-270degC, (Me ester-7-acetate; mp, 93-95degC)(Ref. 0016)
[a]d-22: +4.3deg (C=0.268, MeOH) (Me ester-7-acetate)(Ref. 0001)
nmax cm-1: 3380, 3280, 1705(Ref. 0016)
1H-NMR (Pyridine-d5; 90MHz) d: 18-Me 0.69(s), 19-Me 1.30(s), 7b- H 3.92-4.10(m), and 1a-H 4.12-4.28(m), 3b-H 4.40-4.78(m)(Ref. 0016)
Me-TMS ether (70eV) m/z: 623(M-15), 548(M-TMSOH, 3%), 458(M-2TMSOH, 9%), 368(M-3TMSOH, 16%), 217 (100%)(Ref. 0016)


Isolated from human urine.(Ref. 0001)
Detected in human meconium.(Ref. 0016/0186)
Primary bile acid in pheasant and pigeon.(Ref. 0102)
Biliary bile acid of fruit pigeons and doves (Columbiformes).(Ref. 0102/0103/0166)
Fetal bile acid identified in a dried blood disc, meconium and urine.(Ref. 0190)
Excreted in urine of healthy newborn.(Ref. 0194/0210)
Isolated from human fetal gallbladder bile.(Ref. 0198)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Identified in urine, bile, portal and peripheral venous sera, and liver tissues from subjects with liver diseases (cholestasis, liver cirrhosis, chronic hepatitis, acute hepatitis).(Ref. 0200/0201)
Identified in urine of newborns.(Ref. 0245)




[0001] / [0016] / [0102] / [0103] / [0166] / [0186] / [0190] / [0194] / [0198] / [0199] / [0200] / [0201] / [0210] / [0245]
59
2b,3a,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0059
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

132-134degC, (Me ester; mp, 125-128degC)(Ref. 0015)
nmax cm-1: 1700(C=O), 3350, 1008, 975(OH)(Ref. 0015)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.92(s), 2a- and 3b-H 3.30(brm), 7b-H 3.75(m)(Ref. 0015)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.62(s), 19-Me 0.91(s), 21-Me 0.88(d), 3b-H 3.21(brm), 2a-H 3.47(brm), COOMe 3.62(s), 7b-H 3.78(m)(Ref. 0015)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 43.05, C-2 71.27, C-3 76.94, C-4 37.33, C-5 41.51, C-6 33.97, C-7 68.27, C-8 39.41, C-9 34.26, C-10 37.53, C-11 20.95, C-12 39.68, C-13 42.66, C-14 50.36, C-15 23.65, C-16 28.26, C-17 55.95, C-18 11.80, C-19 22.89, C-20 35.44, C-21 18.35 C-22 31.10, C-23 31.03, C-24 174.88, C-25 51.59(Ref. 0015)
Me-TMS ether (20eV) m/z: 548(M-TMSOH), 458(M-2TMSOH), 369(M-2TMSOH-TMSO, 100%)(Ref. 0015)







[0015]
60
3a,4b,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0060
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

131-133degC, (Me ester; mp, 128-130degC)(Ref. 0017)
nmax cm-1: 1707(C=O), 3420, 1016, 975(OH)(Ref. 0017)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.92(s), 3b-H 3.20(brm), 7b-H 3.81(m), 4a-H 4.10(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.64(s), 19-Me 0.92(s), 21-Me 0.90(d), 3b-H 3.25(brm), COOMe 3.64(s), 7b-H 3.87(m), 4a-H 4.12(dd, J, 10.6, 9.0)(Ref. 0017)
13C-NMR (CDCl3; 22.53MHz) d: C-1 34.6, C-2 28.1, C-3 75.9, C-4 75.5, C-5 47.9, C-6 27.5, C-7 68.5, C-8 39.2, C-9 34.9, C-10 37.1, C-11 20.7, C-12 39.6, C-13 42.7, C-14 50.5, C-15 23.6, C-16 28.1, C-17 55.9, C-18 11.8, C-19 22.9, C-20 35.3, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0017)
Me ester (60eV) m/z: 404(M-H2O, 25%), 386(M-2H2O, 100%), 368(M-3H2O, 14%), 289(M-H2O-SC, 15%), 271(M-2H2O-SC, 24%), 253(M-3H2O-SC, 2%), 244(M-H2O-SC-part of ring D (27), 3%), 229(M-2H2O-SC-ring D (42), 4%), 127(23%)(Ref. 0017)


Isolated from human gallbladder bile.(Ref. 0159/0198)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0163/0188)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Identified in urine of newborns.(Ref. 0245)




[0017] / [0159] / [0163] / [0188] / [0192] / [0198] / [0245]
61
3b,4b,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0061
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

212-214degC, (Me ester; mp, 203-205degC)(Ref. 0017)
nmax cm-1: 1712(C=O), 3372(OH)(Ref. 0017)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 21-Me 0.92(d), 19-Me 0.94(s), 3a- and 7b-H 3.87(m), 4a-H 4.33(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz ) d: 18-Me 0.64(s), 19-Me 0.94(s), 21-Me 0.90(d), COOMe 3.64(s), 7b-H 3.88(m), 3a-H 3.95(m), 4a-H 4.35(dd, J, 11.1, 3.4)(Ref. 0017)
13C-NMR (CDCl3; 22.53MHz) d: C-1 29.2, C-2 25.9, C-3 69.5, C-4 71.4, C-5 42.9, C-6 28.0, C-7 68.6, C-8 39.3, C-9 34.0, C-10 36.9, C-11 20.9, C-12 39.6, C-13 42.7, C-14 50.4, C-15 23.6, C-16 28.1, C-17 55.8, C-18 11.8, C-19 22.9, C-20 35.3, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.3(Ref. 0017)
Me ester (60eV) m/z: 404(M-H2O, 100%), 386(M-2H2O, 39%), 368(M-3H2O, 7%), 289(M-H2O-SC, 19%), 271(M-2H2O-SC, 11%), 253(M-3H2O-SC, 5%), 244(M-2H2O-SC-part of ring D (27), 8%), 247(M-H2O-SC-ring D (42), 7%), 229(M-2H2O-SC-42, 14%), 127(75%)(Ref. 0017)


Excreted in urine of healthy premature and full-term infants.(Ref. 0202)




[0017] / [0202]
62
Cricetocholic Acid
3a,5b,7a-Trihydroxycholan-24-oic Acid
 BBA0062
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

158-159degC, (Me ester-3,7-diacetate)(Ref. 0228)
Me ester-3,7-diasetate: nmax cm-1: 1027, 1366, 1473, 1730, 2873, 2909, 3606(Ref. 0228)
Me ester-3,7-diacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.65(s), 19-Me 0.91(s), 21-Me 0.93(d), 3a- and 7a-OCOMe 2.03 and 2.07(each s), 23-H 2.23(m), 4a-H 2.33(t, J, 12.5), 23'-H 2.35(m), COOMe 3.67(s), 7b-H 4.96(m), 3b-H 5.02(m)(Ref. 0228)
Me ester-3,7-diacetate 13C-NMR (CDCl3; 125MHz) d: C-1 29.3, C-2 26.2, C-3 70.9, C-4 40.5, C-5 74.4, C-6 40.8, C-7 70.9, C-8 36.9, C-9 37.1, C-10 39.5, C-11 20.7, C-12 39.1, C-13 42.4, C-14 50.2, C-15 23.5, C-16 27.8, C-17 55.6, C-18 11.5, C-19 15.7, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.8, C-24 174.8, C-25 51.4(Ref. 0228)
Me ester-3,7-diasetate m/z: 428(10%), 386(84%), 368(82%), 353(23%), 332(100%), 331(35%), 313(39%), 271(85%), 253(42%), 226(33%), 211(37%)(Ref. 0228)


Primary bile acid in pheasant.(Ref. 0102)




[0102] / [0228]
63
1b,3a,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0063
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

262-264degC, (Me ester-12-acetate; mp, 203-205degC)(Ref. 0016)
[a]d-22: +64.4deg (C=0.378, CHCl3) (Me ester-12-acetate)(Ref. 0016)
nmax cm-1: 3400, 3300, 1705(Ref. 0016)
1H-NMR (Pyridine-d5) d: 18-Me 0.75(s), 19-Me 1.34(s), 1a- and 12b-H 4.10-4.36(m), 3b-H 4.58-4.96(m)(Ref. 0016)
Me ester 1H-NMR (CDCl3; 100MHz ) d: 18-Me 0.68(s), 19-Me 1.04(s), COOMe 3.65(s), 12b-H 3.87(m), 1a-H 3.94(m), 3b-H 4.08(brm)(Ref. 0004/0136)
Me-TMS ether (70eV) m/z: 623(M-15), 548(M-TMSOH, 12%), 368(M-3TMSOH, 18%), 253(M-3TMSOH-SC, 6%), 217 (100%)(Ref. 0016/0136)


A hepatic hydroxylation product of deoxycholic acid in sheep.(Ref. 0102)
A microbial transformation product of deoxycholic acid by Penicillium species ATCC 12556.(Ref. 0136)
Identified in serum, faeces, liver tissues and urine from healthy adults and patients with liver cirrhosis.(Ref. 0145/0149/0176/0189/0200)
A hydroxyation metabolite of deoxycholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Bile acid of the human fetus in early gestation.(Ref. 0156)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191/0198)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Excreted in urine of healthy newborn.(Ref. 0194)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Identified in urine, bile, portal and peripheral venous sera, and liver specimens from subjects with liver diseases (cholestasis, liver cirrhosis, chronic hepatitis, acute hepatitis).(Ref. 0201)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)




[0004] / [0016] / [0102] / [0136] / [0145] / [0149] / [0153] / [0156] / [0176] / [0188] / [0189] / [0191] / [0192] / [0194] / [0198] / [0199] / [0200] / [0201] / [0202]
64
Hyocholic Acid
g-Muricholic Acid
3a,6a,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0064
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

188-189degC, (Me ester; mp, 83-85degC)(Ref. 0001)
[a]d-21: +5.5deg (C=1.7, EtOH)(Ref. 0001)
nmax cm-1: 1718 (C=O), 3430, 1050 (OH)(Ref. 0029)
1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.90(s), 21-Me 0.93(d), 3b-H 3.39(brm), 6b- and 7b-H 3.82(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz ) d: 18-Me 0.66(s), 19-Me 0.90(s), 21-Me 0.93(d), 3b-H 3.42-3.48brm), COOMe 3.67(s), 6b- and 7b-H 3.85(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.5, C-2 30.4, C-3 71.7, C-4 32.6, C-5 47.8, C-6 71.9, C-7 69.6, C-8 38.6, C-9 32.5, C-10 35.9, C-11 20.5, C-12 39.5, C-13 42.7, C-14 50.1, C-15 23.0, C-16 28.1, C-17 55.8, C-18 11.7, C-19 23.5, C-20 35.3, C-21 18.2, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0029)
Me ester (70eV) m/z: 422(M+, 16%), 404(M-H2O, 24%), 386(M-2H2O, 23%)(Ref. 0029)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


A primary bile acid in pigs.(Ref. 0101/0102/0167/0215)
Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in urine and serum of healthy humans and patients with malabsorption.(Ref. 0143)
Identified in urine of patients with liver cirrhosis.(Ref. 0145/0149/0150/0151/0163/0176/0189/0200)
Identified in human meconium.(Ref. 0148)
A hydroxylation metabolites of chenodeoxycholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Detected in the bile of germ-free domestic fowl.(Ref. 0169)
Isolated from serum, urine and duodenal fluid of a child with intrahepatic cholestasis.(Ref. 0173)
A fetal bile acid in urine, meconium, and feces.(Ref. 0180/0181/0194)
A fetal bile acid identified in a dried blood disc, meconium and urine.(Ref. 0190)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Identified in urine of a patients treated with chenodeoxycholate, ursodeoxycholate or rifampicin and those with cirrhosis.(Ref. 0193)
Isolated from human fetal gallbladder bile.(Ref. 0198)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Identified in urine, bile, portal and peripheral venous sera, and liver specimens from subjects with liver diseases (cholestasis, liver cirrhosis, chronic hepatitis, acute hepatitis).(Ref. 0201)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in the serum and urine in cholestasis.(Ref. 0203)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Identified in urine of infants during the first year.(Ref. 0210)
Identified in urine of newborns.(Ref. 0245)




[0001] / [0007] / [0029] / [0101] / [0102] / [0124] / [0143] / [0145] / [0148] / [0149] / [0150] / [0151] / [0153] / [0155] / [0163] / [0167] / [0169] / [0173] / [0176] / [0180] / [0181] / [0189] / [0190] / [0191] / [0192] / [0193] / [0194] / [0198] / [0199] / [0200] / [0201] / [0202] / [0203] / [0206] / [0210] / [0215] / [0245]
65
w-Muricholic Acid
b-Hyocholic Acid
3a,6a,7b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0065
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

150-153degC and 184-188degC(Ref. 0001)
[a]d-25: +36deg (C=0.38, MeOH)(Ref. 0001)
nmax cm-1: 1690 (C=O), 3400, 1045 (OH)(Ref. 0029)
1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 19-Me 0.93(s), 3b- and 7a-H 3.40(brm), 6b-H 3.68(brm)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz ) d: 18-Me 0.67(s), 21-Me 0.92(d), 19-Me 0.95(s), 7a-H 3.40(t, J, 9.4), 3b-H 3.55-3.61(brm), COOMe 3.67(s), 6b-H 3.79(dd, J, 9.3, 5.1)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.3, C-2 30.9, C-3 71.2, C-4 29.9, C-5 47.6, C-6 73.0, C-7 75.4, C-8 41.7, C-9 39.7, C-10 35.3, C-11 21.2, C-12 40.0, C-13 43.8, C-14 55.0, C-15 26.7, C-16 28.5, C-17 55.9, C-18 12.2, C-19 23.6, C-20 35.3, C-21 18.4, C-22 31.1, C-23 31.1, C-24 174.6, C-25 51.3(Ref. 0029)
Me ester (70eV) m/z: 422(M+, 7%), 404(M-H2O, 74%), 386(M-2H2O, 83%), 371(M-2H2O-CH3, 16%), 368(M-3H2O, 23%)(Ref. 0029)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


A bacterial biotransformation product in rat.(Ref. 0102)
Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in serum and urine of healthy humans and patients with liver diseases.(Ref. 0149/0150/0151/0163/0187/0193)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
A metabolite of hyodeoxycholic acid in the rat.(Ref. 0215)




[0001] / [0007] / [0029] / [0102] / [0124] / [0149] / [0150] / [0151] / [0163] / [0187] / [0191] / [0193] / [0215]
66
a-Muricholic Acid
3a,6b,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0066
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

200-202degC, (Me ester; mp, 97-98degC)(Ref. 0029)
[a]d-25: +35deg (C=0.514, MeOH)(Ref. 0001)
nmax cm-1: 1710 (C=O), 3400, 1045, 1018 (OH)(Ref. 0029)
1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 21-Me 0.94(d), 19-Me 1.08(s), 3b-H 3.40(brm), 6a- and 7b-H 3.69(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.69(s), 21-Me 0.93(d), 19-Me 1.08(s), 3b-H 3.47-3.53(brm), COOMe 3.66(s), 6a-H 3.72(m), 7b-H 3.73(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.7, C-2 30.1, C-3 71.4, C-4 36.1, C-5 48.0, C-6 76.5, C-7 72.7, C-8 35.3, C-9 32.9, C-10 34.7, C-11 20.4, C-12 39.5, C-13 42.6, C-14 49.9, C-15 23.6, C-16 28.1, C-17 55.8, C-18 11.6, C-19 25.2, C-20 35.1, C-21 18.3, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0029)
Me ester (70eV) m/z: 422 (M+, 1%), 404(M-H2O, 41%), 368(M-2H2O, 60%), 371(M-2H2O-SC, 15%)(Ref. 0029)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from rats.(Ref. 0100/0101/0196/0215)
A primary bile acid in rodent.(Ref. 0102)




[0001] / [0007] / [0029] / [0100] / [0101] / [0102] / [0196] / [0215]
67
b-Muricholic Acid
3a,6b,7b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0067
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

225-227degC(Ref. 0029)
[a]d-26: +64deg (C=0.528, MeOH)(Ref. 0001)
nmax cm-1: 1695 (C=O), 3425, 1052 (OH)(Ref. 0029)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 21-Me 0.94(d), 19-Me 1.08(s), 3b- and 7a-H 3.50(brm), 6a-H 3.61(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.69(s), 21-Me 0.93(d), 19-Me 1.10(s), 7a-H 3.55(dd, J, 9.8, 3.8), 3b-H 3.58-3.64(brm), COOMe 3.67(s), 6a-H 3.70(dd, J, 3.6, 2.5)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.4, C-2 29.9, C-3 70.9, C-4 35.4, C-5 47.2, C-6 75.4, C-7 73.5, C-8 38.5, C-9 39.6, C-10 33.8, C-11 20.8, C-12 39.9, C-13 43.7, C-14 54.9, C-15 27.0, C-16 28.4, C-17 55.5, C-18 12.0, C-19 25.4, C-20 35.2, C-21 18.4, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0029)
13C-NMR (Pyridine-d5; 50.309MHz) d: C1 36.51, C2 30.93, C3 70.83, C4 36.70, C5 48.67, C6 76.44, C7 73.34, C8 39.09, C9 40.37, C10 34.42, C11 21.44, C12 40.56, C13 43.92, C14 56.42, C15 27.80, C16 29.05, C17 55.60, C18 12.52, C19 26.31, C20 35.83, C21 18.91, C22 31.91, C23 31.91, C24 176.67(Ref. 0118)
Me ester (70eV) m/z: 422 (M+, 1%), 404(M-H2O, 100%), 368(M-2H2O, 62%), 371(M-2H2O-SC, 15%)(Ref. 0029)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from rats.(Ref. 0100/0101/0196/0215)
Primary bile acid in rodent.(Ref. 0102)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Isolated from serum, urine and duodenal fluid of a child with intrahepatic cholestasis.(Ref. 0173)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)




[0001] / [0007] / [0029] / [0100] / [0101] / [0102] / [0118] / [0150] / [0151] / [0173] / [0191] / [0196] / [0215]
68
3b,6a,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0068
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

214-217degC(Ref. 0029)
[a]d-25: +5deg (MeOH)(Ref. 0073)
nmax cm-1: 1708(C=O), 3440, 1048(OH)(Ref. 0029)
1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 21-Me 0.92(d), 19-Me 0.94(s), 7b-H 3.84(m), 6b-H 3.90(brm), 3a-H 4.08(m)(Ref. 0029/0073)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.69(s), 19-Me 0.94(s), 21-Me 0.93(d), COOMe 3.66(s), 7b-H 3.86(m), 6h-H 3.95(m), 3a-H 4.12(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 30.0, C-2 27.4, C-3 66.0, C-4 29.3, C-5 42.4, C-6 71.8, C-7 69.5, C-8 38.4, C-9 32.0, C-10 36.4, C-11 20.9, C-12 39.4, C-13 42.7, C-14 50.2, C-15 23.4, C-16 28.0, C-17 55.7, C-18 11.6, C-19 23.6, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0029)
Me ester (70eV) m/z: 422 (M+, 7%), 404(M-H2O, 34%), 386(M-2H2O, 57%), 371(M-2H2O-CH3, 11%)(Ref. 0029)







[0029] / [0073]
69
3b,6a,7b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0069
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

129-131degC(Ref. 0029)
nmax cm-1: 1710(C=O), 3410, 1025(OH)(Ref. 0029)
1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 21-Me 0.92(d), 19-Me 0.95(s), 7a-H 3.33(brm), 6b-H 3.74(brm), 3a-H 4.00(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.68(s), 19-Me 0.99(s), 21-Me 0.92(d), 7a-H 3.38(t, J, 9.1), COOMe 3.67(s), 6b-H 3.86(dd,J,9.3, 5.3), 3a-H 4.14(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.9, C-2 27.3, C-3 65.6, C-4 27.8, C-5 42.3, C-6 73.0, C-7 75.6, C-8 41.6, C-9 38.9, C-10 35.8, C-11 21.5, C-12 40.1, C-13 43.8, C-14 55.1, C-15 26.7, C-16 28.5, C-17 56.0, C-18 12.2, C-19 24.2, C-20 35.2, C-21 18.4, C-22 31.1, C-23 31.1, C-24 174.6, C-25 51.4(Ref. 0029)
Me ester (70eV) m/z: 422 (M+, 8%), 404(M-H2O, 60%), 386(M-2H2O, 73%), 371(M-2H2O-CH3, 13%), 368(M-3H2O, 16%)(Ref. 0029)







[0029]
70
3b,6b,7a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0070
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

214-216degC(Ref. 0029)
nmax cm-1: 1720(C=O), 3420, 1038, 1020(OH)(Ref. 0029)
1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 21-Me 0.94(d), 19-Me 1.11(s), 6a- and 7a-H 3.66(m), 3a-H 4.02(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.70(s), 19-Me 1.12(s), 21-Me 0.93(d), COOMe 3.67(s), 6a-H 3.68(m), 7b-H 3.73(m), 3a-H 4.06(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 30.6, C-2 27.7, C-3 66.3, C-4 33.2, C-5 42.8, C-6 76.6, C-7 73.0, C-8 35.2, C-9 33.0, C-10 35.2, C-11 20.8, C-12 39.5, C-13 42.6, C-14 49.8, C-15 23.7, C-16 28.1, C-17 55.8, C-18 11.7, C-19 25.4, C-20 35.2, C-21 18.2, C-22 31.0, C-23 31.0, C-24 174.7, C-25 51.4(Ref. 0029)
Me ester (70eV) m/z: 422 (M+, 3%), 404(M-H2O, 84%), 386(M-2H2O, 24%), 371(M-2H2O-CH3)(Ref. 0029)







[0029]
71
3b,6b,7b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0071
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

189-190degC(Ref. 0029)
nmax cm-1: 1713(C=O), 3425, 1038(OH)(Ref. 0029)
1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 21-Me 0.94(d), 19-Me 1.12(s), 7a-H 3.43(brm), 6a-H 3.61(m), 3a-H 4.03(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.70(s), 19-Me 1.13(s), 21-Me 0.93(d), 7a-H 3.50(dd,J,10.1, 3.6), 6a-H 3.65(dd, J, 3.6, 2.7), COOMe 3.67(s), 3a-H 4.07(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 30.1, C-2 27.4, C-3 65.7, C-4 32.5, C-5 42.4, C-6 75.0, C-7 73.4, C-8 38.5, C-9 39.2, C-10 34.2, C-11 21.0, C-12 39.9, C-13 43.5, C-14 30.9, C-15 26.9, C-16 28.4, C-17 55.6, C-18 12.0, C-19 25.6, C-20 35.1, C-21 18.3, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.3(Ref. 0029)
Me ester (70eV) m/z: 422 (M+, 6%), 404(M-H2O, 86%), 386(M-2H2O, 40%), 371(M-2H2O-CH3, 9%)(Ref. 0029)







[0029]
72
Allohyocholic Acid
Allo-g-muricholic Acid
3a,6a,7a-Trihydroxy-5a-cholan-24-oic Acid
 BBA0072
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

273-274degC, (Me ester; mp, 210-211degC)(Ref. 0036)
[a]d-25: +30deg (C=0.97, MeOH)(Ref. 0036)
nmax cm-1: 3257, 1709 (COOH), 1163, 1095, 1048, 1010, 962(Ref. 0036)

Me ester (70eV) m/z: 422(M+), 407(M-CH3), 404(M-H2O), 389(M-H2O-CH3), 386(M-2H2O), 373(M-H2O-31), 371(M-2H2O-CH3), 368(M-3H2O), 355(M-2H2O-31), 353(M-3H2O-CH3), 337(M-3H2O-31), 289(M-H2O-SC), 271(M-2H2O-SC), 253(M-3H2O-SC)(Ref. 0036)







[0036]
73
Allo-w-muricholic Acid
3a,6a,7b-Trihydroxy-5a-cholan-24-oic Acid
 BBA0073
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

242-244degC, (Me ester; mp, 192-193degC)(Ref. 0037)
[a]d-25: +19.9deg (C=0.70, MeOH) (Me ester)(Ref. 0036)
nmax cm-1: 1686 (C=O), 3481, 1007 (OH)(Ref. 0037)
1H-NMR (CDCl3+DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.79(s), 21-Me 0.93(s), 21-Me 0.93(d), 6b- and 7a-H 3.02(brm), 3b-H 4.00(m)(Ref. 0037)
Me ester 1H-NMR (CDCl3 +10%MeOH-d6; 500MHz) d: 18-Me 0.689(s), 19-Me 0.820(s), 21-Me 0.934(d), 6b- and 7a-H 3.085(m), COOMe 3.674(s), 3b-H 4.077(brs)(Ref. 0037)
Me ester 13C-NMR (CDCl3 +10%MeOH-d6; 125.65MHz) d: C-1 32.62, C-2 28.66, C-3 65.76, C-4 30.06, C-5 42.10, C-6 75.27, C-7 80.64, C-8 40.95, C-9 52.37, C-10 36.25, C-11 20.96, C-12 40.02, C-13 43.63, C-14 55.11, C-15 26.84, C-16 28.09, C-17 56.18, C-18 12.25, C-19 12.54, C-20 35.50, C-21 18.47, C-22 31.20, C-23 31.27, C-24 175.56, C-25 51.73(Ref. 0037)
Me ester (70eV) m/z: 404(M-H2O, 54%), 386(M-2H2O, 100%), 368(M-3H2O, 48%), 289(M-H2O-SC, 34%), 271(M-2H2O-SC, 49%), 262(M-H2O-SC-part of ring D (27), 21%), 253(M-3H2O-SC, 20%), 244(M-H2O-SC-27, 36%)(Ref. 0037)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from rat bile.(Ref. 0001)




[0001] / [0007] / [0036] / [0037]
74
Allo-a-muricholic Acid
3a,6b,7a-Trihydroxy-5a-cholan-24-oic Acid
 BBA0074
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

261-262degC, (Me ester; mp, 149-150degC)(Ref. 0036)
[a]d-25: 0deg (C=0.63, MeOH)(Ref. 0036)
nmax cm-1: 3444, 1704 (COOH), 1307, 1266, 1166, 1104, 1047, 1000 (3a-OH-5a-)(Ref. 0036)

Me ester m/z: 422(M+), 407(M-CH3), 404(M-H2O), 389(M-H2O-CH3), 386(M-2H2O), 373(M-H2O-31), 371(M-2H2O-CH3), 368(M-3H2O), 355(M-2H2O-31), 353(M-3H2O-CH3), 337(M-3H2O-31), 289(M-H2O-SC), 271(M-2H2O-SC), 253(M-3H2O-SC)(Ref. 0036)







[0036]
75
Allo-b-muricholic Acid
3a,6b,7b-Trihydroxy-5a-cholan-24-oic Acid
 BBA0075
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

256-262degC, (Me ester; mp, 142-144degC)(Ref. 0001/0237)
[a]d-25: +49.5deg (C=0.417, MeOH)(Ref. 0001/0237)
[a]D: +47.9deg (Me ester)(Ref. 0237)
nmax cm-1: 1710 (C=O), 3412, 1035 (OH)(Ref. 0037)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 19-Me 0.96(s), 7a-H 3.26(m), 6a-H 3.54(m), 3b-H 4.08(m)(Ref. 0037)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.671(s), 21-Me 0.902(d), 19-Me 0.953(s), 7a-H 3.296(dd,J, 3.8, 10.0), 6a-H 3.597(t, J, 3.1), COOMe 3.634(s), 3b-H 4.149(t, J, 2.3)(Ref. 0037)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 33.01, C-2 29.16, C-3 66.58, C-4 34.14, C-5 40.20, C-6 74.92, C-7 76.86, C-8 38.26, C-9 52.47, C-10 35.35, C-11 20.56, C-12 39.90, C-13 43.72, C-14 54.97, C-15 27.27, C-16 28.68, C-17 55.47, C-18 12.24, C-19 15.04, C-20 35.45, C-21 18.48, C-22 31.13, C-23 31.09, C-24 174.88, C-25 51.59(Ref. 0037)
Me ester (70eV) m/z: 404(M-H2O, 100%), 386(M-2H2O, 83%), 368(M-3H2O, 38%), 289(M-H2O-SC, 22%), 271(M-2H2O-SC, 19%), 262(M-H2O-SC-part of ring D (27), 71%), 253(M-3H2O-SC, 19%), 244(M-H2O-SC-27, 43%)(Ref. 0037)







[0001] / [0037] / [0237]
76
2b,3a,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0076
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

234-235degC, (Me ester; mp, 191-192degC)(Ref. 0015)
nmax cm-1: 1723(C=O), 3368, 1004(OH)(Ref. 0015)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.92(s), 2a- and 3b-H 3.45(brm), 12b-H 3.92(m)(Ref. 0015)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.64(s), 19-Me 0.90(s), 21-Me 0.93(d), 3b-H 3.35(brm), 2a-H 3.60(brm), COOMe 3.63(s), 12b-H 3.96(m)(Ref. 0015)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 43.60, C-2 70.75, C-3 76.37, C-4 34.50, C-5 42.04, C-6 26.49, C-7 26.16, C-8 36.07, C-9 35.06, C-10 36.58, C-11 28.60, C-12 73.21, C-13 46.6, C-14 47.98 C-15 23.73, C-16 27.57, C-17 47.20, C-18 12.77, C-19 23.01, C-20 35.34, C-21 17.35, C-22 31.32, C-23 31.07, C-24 174.80, C-25 51.54(Ref. 0015)
Me-TMS ether (20eV) m/z: 623(M-CH3), 548(M-TMSOH), 458(M-2TMSOH), 369(M-2TMSOH-TMSO), 343(M-2TMSOH-SC), 253(M-3TMSOH-SC, 100%)(Ref. 0015)







[0015]
77
3a,4b,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0077
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

151-152degC(Ref. 0017)
nmax cm-1: 1706(C=O), 3402, 1036(OH)(Ref. 0017)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.93(s), 21-Me 0.97(d), 3b-H 3.30(brm), 4a-H 3.75(brm), 12b-H 3.92(m)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.66(s), 19-Me 0.93(s), 21-Me 0.94(d), 3b-H 3.37(brm), COOMe 3.64(s), 4a-H 3.73(dd,J, 10.2, 8.6), 12b-H 3.95(t, J, 2.6)(Ref. 0017)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.6, C-2 27.4, C-3 76.7, C-4 72.5, C-5 48.5, C-6 20.8, C-7 25.8, C-8 35.9, C-9 35.4, C-10 36.4, C-11 28.7, C-12 73.0, C-13 46.5, C-14 48.3, C-15 23.6, C-16 27.4, C-17 47.3, C-18 12.7, C-19 23.2, C-20 35.1, C-21 17.3, C-22 31.1, C-23 30.9, C-24 174.6, C-25 51.4 (Ref. 0017)
Me ester (60eV) m/z: 404(M-H2O, 9%), 386(M-2H2O, 9%), 368(M-3H2O, 5%), 289(M-H2O-SC, 100%), 271(M-2H2O-SC, 23%), 253(M-3H2O-SC, 14%), 247(M-H2O-SC-ring D (42), 2%), 229(M-2H2O-SC-42, 3%)(Ref. 0017)







[0017]
78
3b,4b,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0078
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

202-203degC, (Me ester; mp, 189-190degC)(Ref. 0017)
nmax cm-1: 1705(C=O), 3412, 1029(OH)(Ref. 0017)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 19-Me 0.93(s), 21-Me 0.97(d), 4a-H 3.76(brm), 3a- and 12b-H 3.90(m)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.67(s), 19-Me 0.95(s), 21-Me 0.94(d), COOMe 3.64(s), 4a-H 3.89(dd,J, 11.2, 3.0), 12b-H 3.96(t, J, 2.4), 3a-H 3.99(m)(Ref. 0017)
Me ester 13C-NMR (CDCl3 ; 22.53MHz) d: C-1 29.1, C-2 25.7, C-3 68.3, C-4 69.5, C-5 43.9, C-6 20.6, C-7 25.7, C-8 35.7, C-9 34.9, C-10 36.1, C-11 28.9, C-12 73.1, C-13 46.4, C-14 48.3, C-15 23.5, C-16 27.4, C-17 47.2, C-18 12.7, C-19 23.4, C-20 35.0, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0017)
Me ester (60eV) m/z: 404(M-H2O, 4%), 289(M-H2O-SC, 100%), 271(M-2H2O-SC, 23%), 253(M-3H2O-SC, 13%), 265(M-SC-ring D (42), 2%), 229(M-2H2O-SC-42, 2%)(Ref. 0017)







[0017]
79
3a,5b,12a-Trihydroxycholan-24-oic Acid
 BBA0079
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

127-128degC (Me ester-3,12-diacetate)(Ref. 0226)
[a]d-22: +77.3deg (C=1.0, CHCl3) (Me ester-3,12-diacetate)(Ref. 0048)
Me ester-3,12-diacetate: nmax cm-1 (CHCl3): 3617, 1728, 1712, 1699(Ref. 0048)
Me ester-3,12-diacetate 1H-NMR d: 18-Me 0.69(s), 21-Me 0.77(d, J=6.1Hz), 19-Me 0.84(s), 3a-OCOMe 1.99(s), 12a-OCOMe 2.07(s), COOMe 3.63(s), 3b-H 5.03(tt, J, 11.1, 4.7), 12b-H 5.07(m)(Ref. 0048/0226)
Me ester-3,12-diacetate13C-NMR (CDCl3; 125MHz) d: C-1 28.96, C-2 26.01, C-3 71.19, C-4 37.92, C-5 74.80, C-6 36.36, C-7 28.02, C-8 34.50, C-9 36.96, C-10 38.87, C-11 27.11, C-12 75.44, C-13 44.67, C-14 49.28, C-15 23.25, C-16 25.79, C-17 47.29, C-18 12.19, C-19 15.87, C-20 34.64, C-21 17.31, C-22 30.79, C-23 30.64, C-24 174.56, Acetyl Me 21.27,21.15, C=O 170.37, OCH3 51.35(Ref. 0048/0228)
Me ester-3,12-diacetate m/z: 428(29%), 386(21%), 368(84%), 353(24%), 332(55%), 331(53%), 313(40%), 271(44%), 253(100%), 211(24%)(Ref. 0048/0228)







[0048] / [0226] / [0228]
80
3a,6a,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0080
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

135-137degC(Ref. 0030)
154-155degC (Me ester-3,6-diacetate)(Ref. 0001)
150-151degC (Me ester-3,6,12-triacetate)(Ref. 0217)
[a]D: +18deg (dioxane)(Ref. 0001)
nmax cm-1: 1709 (C=O), 3401, 1037 (OH)(Ref. 0030)
1H-NMR (CDCl3; 90MHz) d: 18-Me 0.67(s), 19-Me 0.89(s), 21-Me 0.99(d), 3b-H 3.58(brm), 6b- and 12b-H 4.03(m and brm)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 500MHz)d: 18-Me 0.666(s), 19-Me 0.890(s), 21-Me 0.967(d), 3b-H 3.583(brm), COOMe 3.663(s), 12b-H 3.977(m), 4b-H 4.007(brm)(Ref. 0030)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.66, C-2 30.08, C-3 71.53, C-4 29.18, C-5 48.53, C-6 68.08, C-7 34.81, C-8 35.10, C-9 32.97, C-10 35.60, C-11 28.62, C-12 72.95, C-13 46.69, C-14 47.87, C-15 23.81, C-16 27.51, C-17 47.27, C-18 12.73, C-19 23.28, C-20 35.27, C-21 17.32, C-22 31.18, C-23 30.96, C-24 174.85, C-25 51.59(Ref. 0030)
Me ester (70eV) m/z: 404(M-H2O, 7%), 386(M-2H2O, 81%), 368(M-3H2O, 23%), 289(M-H2O-SC, 20%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 67%)(Ref. 0030)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from urine of healthy subjects, a patient with malabsorption and a patient with moderate cholestasis of pregnancy.(Ref. 0001/0143/0144)
A hydroxyation metabolite of deoxycholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Bile acid of human fetus in early gestation.(Ref. 0156)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Identified in urine of infants during the first year.(Ref. 0210)




[0001] / [0007] / [0030] / [0143] / [0144] / [0153] / [0156] / [0206] / [0210] / [0217]
81
3a,6b,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0081
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

137-139degC(Ref. 0030)
[a]d-26: +36deg (C=0.406, 95%EtOH)(Ref. 0216)
nmax cm-1: 1711 (C=O), 3401, 1045 (OH)(Ref. 0030)
1H-NMR (CDCl3; 90MHz)d: 18-Me 0.71(s), 21-Me 0.98(d), 19-Me 1.09(s), 3b-H 3.62(brm), 6a-H 3.62(m), 12b-H 3.98(m)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.712(s), 19-Me 1.099(s), 21-Me 0.976(d), 3b-H 3.598(brm), COOMe 3.665(s), 6a-H 3.776(m), 12b-H 4.006(m)(Ref. 0030)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.76, C-2 30.12, C-3 71.30, C-4 36.44, C-5 48.68, C-6 73.13, C-7 34.45, C-8 30.96, C-9 34.06, C-10 33.97, C-11 28.51, C-2 73.13, C-13 46.63, C-14 48.00, C-15 23.70, C-16 27.51, C-17 47.41, C-18 12.86, C-19 25.41, C-20 35.16, C-21 17.43, C-22 31.17, C-23 30.96, C-24 174.78, C-25 51.59(Ref. 0030)
Me ester (70eV) m/z: 404(M-H2O, 4%), 386(M-2H2O, 28%), 368(M-3H2O, 12%), 289(M-H2O-SC, 19%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 34%)(Ref. 0030)


Identified in urine of healthy humans and patients with liver diseases.(Ref. 0143/0150/0151)
Constituent of a urinary bile acid in late prenancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Identified in urine of infants during the first year.(Ref. 0210)




[0030] / [0143] / [0150] / [0151] / [0206] / [0210] / [0216]
82
3b,6a,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0082
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

135-137degC, (Me ester; mp, 115-117degC)(Ref. 0030)
nmax cm-1: 1709 (C=O), 3412, 1036, 976 (OH)(Ref. 0030)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.92(s), 21-Me 0.96(d), 12b-H 3.96(m), 6b-H 4.00(brm), 3a-H 4.08(m)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.680(s), 19-Me 0.929(s), 21-Me 0.973(d), COOMe 3.664(s), 12b-H 3.993(m), 6b-H 4.119(brm), 3a-H 4.156(m)(Ref. 0030)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 30.08, C-2 27.43, C-3 66.09, C-4 26.25, C-5 43.05, C-6 67.85, C-7 34.37, C-8 34.93, C-9 32.33, C-10 36.05, C-11 28.93, C-12 73.04, C-13 46.75, C-14 48.12, C-15 23.67, C-16 27.43, C-17 47.42, C-18 12.78, C-19 23.84, C-20 35.13, C-21 17.40, C-22 31.12, C-23 30.93, C-24 174.78, C-25 51.59(Ref. 0030)
Me ester (70eV) m/z: 404(M-H2O, 6%), 386(M-2H2O, 42%), 289(M-H2O-SC, 79%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 39%)(Ref. 0030)







[0030]
83
3b,6b,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0083
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

131-133degC, (Me ester; mp, 196-197degC)(Ref. 0030)
nmax cm-1: 1709 (C=O), 3408, 1023 (OH)(Ref. 0030)Me ester: nmax m: 9.31, 9.64, 9.85, 10.21, 10.54(Ref. 0003)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.70(s), 21-Me 0.98(d), 19-Me 1.11(s), 6a-H 3.66(m), 3a- and 12b-H 3.99(m)(Ref. 0030)
Me ester 1H-NMR (CDCl3+20%DMSO-d6; 500MHz) d: 18-Me 0.686(s), 21-Me 0.983(d), 19-Me 1.101(s), COOMe 3.640(s), 6a-H 3.602(m), 12b-H 3.925(m), 3a-H 3.973(m)(Ref. 0030)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 29.43, C-2 26.50, C-3 64.44 C-4 32.24, C-5 42.23, C-6 71.38, C-7 33.42, C-8 29.91, C-9 32.86, C-10 33.48, C-11 28.04, C-12 71.58, C-13 45.57, C-14 47.05, C-15 22.86, C-16 26.64, C-17 45.84, C-18 11.91, C-19 24.99, C-20 34.37, C-21 16.36, C-22 30.09, C-23 29.91, C-24 173.65, C-25 50.49(Ref. 0030)
Me ester (70eV) m/z: 404(M-H2O, 2%), 386(M-2H2O, 18%), 289(M-H2O-SC, 14%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 19%)(Ref. 0030)







[0003] / [0030]
84
Cholic Acid
3a,7a,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0084
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

197degC, (Me ester; mp, 162degC)(Ref. 0001)
176-178degC (Me ester-3,7-diacetate)(Ref. 0247)
[a]d-20: +37deg (EtOH), [a]d-20: +25deg (Me ester)(Ref. 0001)
Me ester 1H-NMR(CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.87(s), 21-Me 0.97(d), 3b-H 3.5(brm), 7b-H 3.75(m), 12b-H 3.88(m)(Ref. 0004/0005)
Me ester-3,7-diacetate 1H-NMR(CDCl3) d: 18-Me 0.68(s), 19-Me 0.96(s), 21-Me 1.00(d), 3a- and 7a-OCOMe 2.05, 2.10(each s), 23-H2 2.25(m), COOMe 3.65(s), 12b-H 3.95(m), 3b-H 4.59(brm), 7b-H 4.85(m)(Ref. 0247)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 35.3, C-2 30.1, C-3 71.7 C-4 39.4, C-5 41.4, C-6 34.7, C-7 68.3, C-8 39.4, C-9 26.2, C-10 34.7, C-11 28.0, C-12 73.0, C-13 46.3, C-14 41.4, C-15 23.1, C-16 27.4, C-17 46.8, C-18 12.3, C-19 22.3, C-20 35.3, C-21 17.4, C-22 31.0, C-23 31.0, C-24 174.7, C-25 51.4(Ref. 0006)
Me ester (70eV) m/z: 402(M-H2O, 2%), 386(M-2H2O, 43%), 371(M-2H2O-CH3, 8%), 368(M-3H2O, 28%), 353(M-3H2O-CH3, 10%), 289(M-H2O-SC, 10%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 86%), 226(M-3H2O-SC-part of ring D (27), 20%)(Ref. 0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)
Me ester-3,7,12-triacetate (70eV) m/z: 548(M, 1%), 488(M-AcOH, 3%), 428(M-2AcOH, 3%), 368(M-3AcOH, 48%), 313(M-SC, 42%), 253(100%), 211(18%), 413(3%), 353(21%), 286(6%), 281(9%), 274(4%), 271(3%), 261(7%), 226(20%)(Ref. 0231)
Me ester-3,7-diacetate (70eV) m/z: 506(M, 1%), 446(M-AcOH, 3%), 386(M-2AcOH, 10%), 313(M-SC, 38%), 253(100%), 211(14%), 428(24%), 413(3%), 368(38%), 353(14%), 286(10%), 281(14%), 271(14%), 261(21%), 226(14%)(Ref. 0231)


Widespread bile acid found in the biological fluids of most vertebrates.(Ref. 0001/0101)
Common primary bile acid.(Ref. 0100/0102)
Identified in urine and feces of healthy humans and patients with liver diseases.(Ref. 0150/0151/0162)
Identified in plasma of patients with bacterial overgrowth in the small intestine.(Ref. 0256)




[0001] / [0004] / [0005] / [0006] / [0007] / [0010] / [0100] / [0101] / [0102] / [0150] / [0151] / [0162] / [0231] / [0247] / [0256]
85
Lagocholic Acid
3a,7a,12b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0085
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

200.0-201.5degC(Ref. 0032)
[a]D: +30.5deg (EtOH), [a]D: +14.0deg (Me ester)(Ref. 0032)
Me ester: nmax cm-1: 1724 (ester C=O)(Ref. 0032)
1H-NMR (CD3COCD3+D2O) d: 18-Me 0.71(s), 19-Me 0.91(s), 3b- and 12a-H 3.40(brm)(Ref. 0005/0032)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.72(s), 19-Me 0.90(s), 3b- and 12a-H 3.40(brm), COOMe 3.54(s), 7b-H 3.86(m)(Ref. 0032)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.8, C-2 30.6, C-3 71.4 C-4 39.3, C-5 41.2, C-6 35.2, C-7 67.7, C-8 38.0, C-9 32.0, C-10 34.8, C-11 29.3, C-12 78.9, C-13 47.5, C-14 47.2, C-15 26.1, C-16 23.7, C-17 57.0, C-18 7.6, C-19 22.5, C-20 32.5, C-21 20.9, C-22 32.1, C-23 30.8, C-24 174.7, C-25 51.3(Ref. 0006)
Me ester (70eV) m/z: 402(M-H2O, 2%), 386(M-2H2O, 13%), 371(M-2H2O-CH3, 4%), 368(M-3H2O, 5%), 353(M-3H2O-CH3, 2%), 289(M-H2O-SC, 9%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 36%), 226(M-3H2O-SC-part of ring D (27), 3%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 623(M-CH3, 7%), 548(M-TMSOH, 1%), 458(M-2TMSOH, 48%), 368(M-3TMSOH, 25%), 343(76%), 253(100%), 73(50%)(Ref. 0007/0049)


Identified in urine specimens from healthy humans.(Ref. 0212)




[0005] / [0006] / [0007] / [0010] / [0032] / [0049] / [0212]
86
3b7a,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0086
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

196.5-197.0degC, (Me ester; mp, 185.0-187.0degC)(Ref. 0032)
[a]D: +31deg (MeOH)(Ref. 0073)
1H-NMR (DMSO-d6; 270MHz) d: 18-Me 0.59(s), 19-Me 0.83(s), 21-Me 0.92(d), 7b-H 3.61(q, J=3.0), 3a- and 12b-H (m)(Ref. 0073)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.68(s), 19-Me 0.91(s), COOMe 3.64(s), 7b-H 3.86(m), 3a- and 12b-H 4.01(m)(Ref. 0005/0032)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.8, C-2 27.7, C-3 66.9 C-4 36.6, C-5 35.9, C-6 35.2, C-7 68.5, C-8 39.5, C-9 25.9, C-10 34.3, C-11 28.6, C-12 72.8, C-13 46.6, C-14 41.9, C-15 23.2, C-16 27.4, C-17 47.2, C-18 12.5, C-19 22.9, C-20 35.2, C-21 17.4, C-22 31.1, C-23 30.9, C-24 174.7, C-25 51.4(Ref. 0006)
Me ester (70eV) m/z: 402(M-H2O, 1%), 386(M-2H2O, 50%), 371(M-2H2O-CH3, 8%), 368(M-3H2O, 4%), 353(M-3H2O-CH3, 3%), 289(M-H2O-SC, 8%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 25%), 226(M-3H2O-SC-part of ring D (27), 2%)(Ref. 0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Detected as a trace component of feces of human and dog.(Ref. 0101/0162)Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)




[0005] / [0006] / [0007] / [0010] / [0032] / [0073] / [0101] / [0155] / [0162] / [0191]
87
3b,7a,12b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0087
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

225-226degC(Ref. 0032)
[a]D: +23.4deg (EtOH), [a]D: +17.0deg (Me ester)(Ref. 0032)
Me ester: nmax cm-1: 1721 (C=O)(Ref. 0032)
1H-NMR (CD3COCD3+D2O; 100MHz) d: 18-Me 0.73(s), 19-Me 0.95(s), 12a-H 3.43(brm), 7b-H 3.82(m), 3a-H 3.97(m)(Ref. 0032)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.73(s), 19-Me 0.95(s), 12a-H 3.45(brm), COOMe 3.66(s), 7b-H 3.88(m), 3a-H 4.04(m)(Ref. 0005/0032)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.8, C-2 27.7, C-3 66.6 C4 36.5, C-5 35.7, C-6 35.4, C-7 68.2, C-8 38.0, C-9 31.3, C-10 34.4, C-11 29.3, C-12 79.0, C-13 47.6, C-14 48.6, C-15 23.1, C-16 23.8, C-17 57.1, C-18 7.7, C-19 23.0, C-20 32.6, C-21 21.0, C-22 32.1, C-23 31.2, C-24 174.7, C-25 51.4(Ref. 0006)
Me ester (70eV) m/z: 402(M-H2O, 2%), 386(M-2H2O, 11%), 371(M-2H2O-CH3, 4%), 289(M-H2O-SC, 10%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 8%)(Ref. 0010)







[0005] / [0006] / [0010] / [0032]
88
Ursocholic Acid
7-Epicholic Acid
3a,7b,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0088
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

128.0-131.0degC(Ref. 0031)
[a]D: +62deg (dioxane)(Ref. 0001)
nmax cm-1: 1704 (C=O), 3448, 1042, 1010, 957 (OH)(Ref. 0031)
1H-NMR (CDCl3+10%DMSO-d6+D2O; 100MHz) d: 18-Me 0.69(s), 19-Me 0.91(s), 3b- and 7a-H 3.51(brm), 12b-H 3.91(m)(Ref. 0031)
as Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.71(s), 19-Me 0.93(s), 3b- and 7a-H 3.59(brm), COOMe 3.64(s), 12b-H 3.98(m)(Ref. 0005/0031)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.2, C-2 29.1, C-3 71.0 C-4 36.9, C-5 42.6, C-6 36.6, C-7 71.0, C-8 43.5, C-9 31.2, C-10 33.9, C-11 27.7, C-12 72.2, C-13 47.5, C-14 47.2, C-15 26.1, C-16 27.4, C-17 45.7, C-18 12.6, C19 23.4, C-20 34.8, C-21 17.2, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0006)
Me ester (70eV) m/z: 386(M-2H2O, 15%), 371(M-2H2O-CH3, 3%), 368(M-3H2O, 11%), 353(M-3H2O-CH3, 6%), 289(M-H2O-SC, 74%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 91%), 226(M-3H2O-SC-part of ring D (27), 5%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 623(M-CH3, 1%), 548(M-TMSOH, 3%), 458(M-2TMSOH, 14%), 368(M-3TMSOH, 17%), 433(7%), 343(26%), 253(100%), 73(35%)(Ref. 0007/0049)


Detected in the feces of human, dog, and rat, in human bile, and in the bile of the rat.(Ref. 0101/0162)
Identified in urine and serum of healthy humans and patients with liver diseases.(Ref. 0145/0150/0151/0187/0203)
Occurred in the bile of patients with gallstones.(Ref. 0172)
Identified in urine of a patients treated with chenodeoxycholate, ursodeoxycholate or rifampicin and those with cirrhosis.(Ref. 0193)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in urine of infants during the first year.(Ref. 0210)




[0001] / [0005] / [0006] / [0007] / [0010] / [0031] / [0049] / [0101] / [0145] / [0150] / [0151] / [0162] / [0172] / [0187] / [0193] / [0202] / [0203] / [0210]
89
3a,7b,12b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0089
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

191.5-193.0degC(Ref. 0031)
nmax cm-1: 1701 (C=O), 3636, 3448, 1049, 1010, 954 (OH)(Ref. 0031)
1H-NMR (CDCl3+10%DMSO-d6+D2O; 100MHz) d: 18-Me 0.71(s), 19-Me 0.92(s), 3b-, 7a- and 12a-H 3.44(brm)(Ref. 0031)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.76(s), 19-Me 0.96(s), 3b-, 7a-and 12a-H 3.52(brm)(Ref. 0005/0031)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.8, C-2 30.1, C-3 70.6 C-4 36.9, C-5 42.1, C-6 36.9, C-7 70.6, C-8 42.1, C-9 37.9, C-10 33.8, C-11 29.1, C-12 79.1, C-13 48.6, C-14 54.2, C-15 26.2, C-16 23.8, C-17 56.5, C-18 8.0, C-19 23.1, C-20 32.3, C-21 21.0, C-22 32.1, C-23 31.2, C-24 174.8, C-25 51.4(Ref. 0006)
Me ester (70eV) m/z: 402(M-H2O, 2%), 386(M-2H2O, 18%), 371(M-2H2O-CH3, 4%), 368(M-3H2O, 6%), 353(M-3H2O-CH3, 3%), 289(M-H2O-SC, 51%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 62%), 226(M-3H2O-SC-part of ring D (27), 3%)(Ref. 0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0005] / [0006] / [0007] / [0010] / [0031]
90
3b,7b,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0090
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

164.5-165.5degC(Ref. 0031)
nmax cm-1: 1730 (C=O), 3636, 3509, 1031, 1020, 990, 954 (OH)(Ref. 0031)
1H-NMR (CDCl3+10%DMSO-d6+D2O; 100MHz) d: 18-Me 0.70(s), 19-Me 0.94(s), 7a-H 3.56(brm), 3a- and 12b-H 3.96(m)(Ref. 0031)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.71(s), 19-Me 0.96(s),7a-H 3.58(brm), COOMe 3.64(s), 12b-H 3.9(m), 3a-H 4.06(m)(Ref. 0005/0031)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.3, C-2 27.7, C-3 66.2 C-4 34.3, C-5 36.9, C-6 36.6, C-7 71.0, C-8 43.5, C-9 31.2, C-10 33.9, C-11 29.2, C-12 72.2, C-13 47.5, C-14 47.2, C-15 26.1, C-16 27.4, C-17 45.8, C-18 12.6, C-19 23.4, C-20 34.8, C-21 17.2, C-22 30.9, C-23 30.8, C-24 174.5, C-25 51.3(Ref. 0006)
Me ester (70eV) m/z: 402(M-H2O, 1%), 386(M-2H2O, 14%), 371(M-2H2O-CH3, 4%), 368(M-3H2O, 3%), 353(M-3H2O-CH3, 2%), 289(M-H2O-SC, 53%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 32%), 226(M-3H2O-SC-part of ring D (27), 2%)(Ref. 0010)


Detected as a component of human feces.(Ref. 0101/0162)Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Identified in urine of infants during the first year.(Ref. 0210)




[0005] / [0006] / [0010] / [0031] / [0101] / [0150] / [0151] / [0162] / [0206] / [0210]
91
3b,7b,12b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0091
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

164.5-167.0degC(Ref. 0031)
nmax cm-1: 1695 (C=O), 3448, 3333, 1020, 1004, 957 (OH)(Ref. 0031)
1H-NMR (CDCl3+10%DMSO-d6+D2O; 100MHz) d: 18-Me 0.70(s), 19-Me 0.94(s), 7a- and 12a-H 3.40(brm), 3a-H 3.93(m)(Ref. 0031)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.76(s), 19-Me 0.98(s), 7a- and 12a-H 3.42(brm), COOMe 3.63(s), 3a-H 4.07(m)(Ref. 0005/0031)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.0, C-2 27.6, C-3 66.1 C-4 34.4, C-5 36.9, C-6 36.7, C-7 71.0, C-8 42.1, C-9 37.2, C-10 34.4, C-11 29.5, C-12 79.3, C-13 48.6, C-14 53.9, C-15 26.2, C-16 23.6, C-17 56.4, C-18 8.0, C-19 23.6, C-20 32.3, C-21 21.1, C-22 32.3, C-23 31.4, C-24 174.7, C-25 51.4(Ref. 0006)
Me ester (70eV) m/z: 402(M-H2O, 2%), 386(M-2H2O, 15%), 371(M-2H2O-CH3, 5%), 289(M-H2O-SC, 61%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 27%)(Ref. 0010)







[0005] / [0006] / [0010] / [0031]
92
Allocholic Acid
3a,7a,12a-Trihydroxy-5a-cholan-24-oic Acid
 BBA0092
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

254-257degC, (Me ester; mp, 228-230degC)(Ref. 0024/0237)
[a]d-25: +27.8pm0.1deg (C=0.75, MeOH)(Ref. 0038/0237)
[a]d-25: +26.7deg (C=0.84, MeOH) (Me ester)(Ref. 0001/0237)
nmax cm-1: 1709 (C=O), 3400, 1031, 1011 (OH)(Ref. 0024)
1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.66(s), 19-Me 0.74(s), 21-Me 0.98(d), 7b-H 3.71(m), 12b-H 3.86(m), 3b-H 3.95(m)(Ref. 0024)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.77(s), 21-Me 0.98(d), COOMe 3.66(s), 7b-H 3.83(m), 12b-H 3.95(m), 3b-H 4.05(m)(Ref. 0008/0024)
>Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 31.9, C-2 28.8, C-3 66.3, C-4 35.5, C-5 31.5, C-6 36.3, C-7 67.9, C-8 39.8, C-9 39.2, C-10 35.8, C-11 28.1, C-12 72.8, C-13 46.4, C-14 42.1, C-15 23.0, C-16 27.3, C-17 47.1, C-18 12.5, C-19 9.9, C-20 35.1, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.6, C-25 51.3(Ref. 0011)
Me ester (70eV) m/z: 404(M-H2O, 1%), 386(M-2H2O, 69%), 371(M-2H2O-CH3, 8%), 289(M-H2O-SC, 15%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 19%)(Ref. 0012/0024/0033)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from many animal sources such as fishes, birds, penguins, sturgeons, and mammals.(Ref. 0001/0085/0101)
Identified in lizards, snakes, birds, and rabbits.(Ref. 0100)
Identified in urine, feces, and meconium of healthy humans and patients with liver diseases.(Ref. 0145/0148/0150/0151/0162)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Isolated from the leopard seal, Hydrurga leptonyx, and the California sealion, Zalophus californianus.(Ref. 0168)
Detected in the bile of germ-free domestic fowl.(Ref. 0169)
A metabolite of 5a-cholestan-3b-ol in the rat.(Ref. 0177)
Isolated from bile of patients with cerebrotendinous xanthomatosis.(Ref. 0178)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Identified in urine of infants during the first year.(Ref. 0210)
A biotransformation product of 7a-hydroxycholesterol in the hen.(Ref. 0214)




[0001] / [0007] / [0008] / [0011] / [0012] / [0024] / [0033] / [0038] / [0085] / [0100] / [0101] / [0145] / [0148] / [0150] / [0151] / [0155] / [0162] / [0168] / [0169] / [0177] / [0178] / [0191] / [0202] / [0206] / [0210] / [0214] / [0237]
93
3a,7a,12b-Trihydroxy-5a-cholan-24-oic Acid
 BBA0093
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

210.5-212degC, (Me ester; mp, 126-127.5degC)(Ref. 0033)
nmax cm-1: 1700(C=O), 3450, 1010, 995(OH)(Ref. 0033)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 19-Me 0.74(s), 21-Me 1.00(d), 12a-H 3.32(brm), 7b-H 3.69(m), 3b-H 3.90(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 19-Me 0.79(s), 21-Me 1.01(d), 12a-H 3.41(brm), COOMe 3.66(s), 7b-H 3.85(m), 3b-H 4.06(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.2, C-2 28.8, C-3 66.2, C-4 35.4, C-5 31.4, C-6 36.4, C-7 67.5, C-8 38.3, C-9 44.8, C-10 36.0, C-11 29.5, C-12 78.9, C-13 47.6, C-14 48.7, C-15 23.0, C-16 23.8, C-17 57.2, C-18 7.7, C-19 10.0, C-20 32.7, C-21 20.9, C-22 31.9, C-23 30.9, C-24 174.7, C-25 51.4(Ref. 0011)
Me ester (20eV) m/z: 404(M-H2O, 5%), 386(M-2H2O, 19%), 289(M-H2O-SC, 31%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 6%)(Ref. 0012/0033)







[0008] / [0011] / [0012] / [0033]
94
3b,7a,12a-Trihydroxy-5a-cholan-24-oic Acid
 BBA0094
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

236-238degC, (Me ester; mp, 200-202degC)(Ref. 0033/0237)
[a]d-25: +25.2pm1deg (C=0.68, MeOH)(Ref. 0038/0237)
[a]d-25: +23.2deg (Me ester)(Ref. 0237)
nmax cm-1: 1705(C=O), 3420, 1035(OH)(Ref. 0033)
The spectrum was shown as its Et ester derivative(Ref. 0085)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.79(s), 21-Me 0.99(d), 3a-H 3.53(brm), 7b-H 3.78(m), 12b-H 3.91(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.80(s), 21-Me 0.98(d), 3a-H 3.61(brm), COOMe 3.66(s), 7b-H 3.82(m), 12b-H 3.95(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.6, C-2 31.3, C-3 71.0, C-4 37.7, C-5 37.1, C-6 36.5, C-7 67.7, C-8 39.8, C-9 39.3, C-10 35.1, C-11 28.6, C-12 72.8, C-13 46.5, C-14 42.0, C-15 23.0, C-16 27.3, C-17 47.2, C-18 12.5, C-19 11.0, C-20 35.1, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0011)
Me ester (20eV) m/z: 404(M-H2O, 4%), 386(M-H2O, 87%), 289(M-H2O-SC, 30%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 12%)(Ref. 0012/0033)







[0008] / [0011] / [0012] / [0033] / [0038] / [0085] / [0237]
95
3b,7a,12b-Trihydroxy-5a-cholan-24-oic Acid
 BBA0095
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

242-243degC, (Me ester; mp, 110-111degC)(Ref. 0033)
nmax cm-1: 1675(C=O), 3200, 1010(OH)(Ref. 0033)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.78(s), 21-Me 1.01(d), 3a- and 12a-H 3.36(brm), 7b-H 3.73(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.73(s), 19-Me 0.82(s), 21-Me 1.01(d), 3a- and 12a-H 3.46(brm), COOMe 3.66(s), 7b-H 3.86(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.6, C-2 31.0, C-3 70.3, C-4 37.3, C-5 36.9, C-6 36.4, C7 66.8, C-8 38.0, C-9 44.4, C-10 35.2, C-11 29.3, C-12 78.4, C-13 47.3, C-14 48.2, C-15 22.7, C-16 23.6, C-17 56.9, C-18 7.4, C-19 10.8, C-20 32.3, C-21 20.6, C-22 31.9, C-23 31.0, C-24 174.2, C-25 50.9(Ref. 0011)
Me ester (20eV) m/z: 404(M-H2O, 6%), 386(M-2H2O, 16%), 289(M-H2O-SC, 42%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 4%)(Ref. 0012/0033)







[0008] / [0011] / [0012] / [0033]
96
Alloursocholic Acid
3a,7b,12a-Trihydroxy-5a-cholan-24-oic Acid
 BBA0096
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

269-271degC, (Me ester; mp, 166-167degC)(Ref. 0033/0237)
[a]D: +61.0deg(Ref. 0013/0237)
nmax cm-1: 1675(C=O), 3500, 1025, 1000(OH)(Ref. 0033)
1H-NMR (CDCl3+50%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 19-Me 0.74(s), 21-Me 0.97(d), 7a-H 3.24(brm), 3b- and 12b-H 3.88(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.79(s), 21-Me 0.98(d), 7a-H 3.35(brm), COOMe 3.66(s), 3b- and 12b-H 4.00(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 31.9, C-2 28.8, C-3 65.7, C-4 35.4, C-5 36.1, C-6 38.2, C-7 74.6, C-8 43.4, C-9 45.1, C-10 34.8, C-11 28.4, C-12 72.1, C-13 47.1, C-14 47.4, C-15 26.2, C-16 27.6, C-17 45.7, C-18 12.6, C-19 10.9, C-20 34.8, C-21 17.2, C-22 30.9, C-23 30.8, C-24 174.4, C-25 51.1(Ref. 0011)
Me ester (20eV) m/z: 404(M-H2O, 2%), 386(M-2H2O, 22%), 289(M-H2O-SC, 96%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 22%)(Ref. 0012/0033)


Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Isolated from bile of patients with cerebrotendinous xanthomatosis.(Ref. 0178)




[0008] / [0011] / [0012] / [0013] / [0033] / [0150] / [0151] / [0178] / [0237]
97
3a,7b,12b-Trihydroxy-5a-cholan-24-oic Acid
 BBA0097
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

243-244degC, (Me ester; mp, 178-179degC)(Ref. 0033)
[a]D: +50deg (EtOH)(Ref. 0001)
nmax cm-1: 1735, 1710(C=O), 3280, 1028, 1005(OH)(Ref. 0033)
1H-NMR (CDCl3+50%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.75(s), 21-Me 0.97(d), 7a- and 12a-H 3.27(brm), 3b-H 3.86(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.74(s), 19-Me 0.79(s), 21-Me 0.99(d), 7a- and 12a-H 3.33(brm), COOMe 3.65(s), 3b-H 3.97(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 31.5, C-2 28.1, C-3 64.4, C-4 34.8, C-5 35.5, C-6 38.0, C-7 73.4, C-8 41.2, C-9 50.5, C-10 34.5, C-11 28.6, C-12 78.4, C-13 47.6, C-14 53.3, C-15 25.6, C-16 23.0, C-17 55.8, C-18 7.4, C-19 10.5, C-20 31.7, C-21 20.4, C-22 31.5, C-23 30.3, C-24 173.6, C-25 50.4 (Ref. 0011)
Me ester (20eV) m/z: 404(M-H2O, 6%), 386(M-2H2O, 26%), 289(M-H2O-SC, 100%), 271(M-2H2O-SC, 52%), 253(M-3H2O-SC, 16%)(Ref. 0012/0033)







[0001] / [0008] / [0011] / [0012] / [0033]
98
3b,7b,12a-Trihydroxy-5a-cholan-24-oic Acid
 BBA0098
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

252-254degC, (Me ester; mp, 149-151degC)(Ref. 0033)
nmax cm-1: 1680(C=O), 3440, 1027(OH)(Ref. 0033)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.79(s), 21-Me 0.98(d), 3a- and 7a-H 3.34(brm), 12b-H 3.87(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.83(s), 21-Me 0.98(d), 3a- and 7a-H 3.40(brm), COOMe 3.66(s), 12b-H 3.97(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.7, C-2 31.3, C-3 70.9, C-4 37.7, C-5 42.1, C-6 38.3, C-7 74.8, C-8 43.5, C-9 45.1, C-10 34.5, C-11 29.0, C-12 72.4, C-13 47.4, C-14 47.4, C-15 26.2, C-16 27.4, C-17 46.0, C-18 12.7, C-19 12.2, C-20 34.9, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.5, C-25 51.4(Ref. 0011)
Me ester (20eV) m/z: 404(M-H2O, 3%), 386(M-2H2O, 22%), 289(M-H2O-SC, 100%), 271(M-2H2O-SC, 93%), 253(M-3H2O-SC, 13%)(Ref. 0012/0033)


Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)




[0008] / [0011] / [0012] / [0033] / [0150] / [0151] / [0191]
99
3b,7b,12b-Trihydroxy-5a-cholan-24-oic Acid
 BBA0099
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

227-228degC, (Me ester; mp, 165-166degC)(Ref. 0033)
nmax cm-1: 1673(C=O), 3450, 1035, 1003(OH)(Ref. 0033)
1H-NMR (CDCl3+50%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.77(s), 21-Me 0.96(d), 3a- , 7a- and 12a-H 3.31(brm)(Ref. 0033)
Me ester 1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.76(s), 19-Me 0.84(s), 21-Me 0.99(d), 3a-, 7a- and 12a-H 3.40(m), COOMe 3.66(s)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.4, C-2 30.9, C-3 70.5, C-4 37.1, C-5 41.4, C-6 37.8, C-7 74.3, C-8 41.6, C-9 50.7, C-10 34.4, C-11 28.7, C-12 78.9, C-13 48.1, C-14 53.3, C-15 25.8, C-16 23.2, C-17 56.1, C-18 7.6, C-19 11.9, C-20 32.0, C-21 21.0, C-22 31.8, C-23 31.1, C-24 174.2, C-25 50.9(Ref. 0011)
Me ester (20eV) m/z: 404(M-H2O, 5%), 386(M-2H2O, 21%), 289(M-H2O-SC, 100%), 271(M-2H2O-SC, 50%), 253(M-3H2O-SC, 8%)(Ref. 0012/0033)







[0008] / [0011] / [0012] / [0033]
100
(22R)-3a,7a,22-Trihydroxy-5b-cholan-24-oic Acid
 BBA0100
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

141-142degC(Ref. 0050)
110-112degC (Et ester-3,7-diacetate)(Ref. 0264)
[a]D: +1.0deg (C=1.3, MeOH)(Ref. 0050)
nmax cm-1: 3400 (OH), 1720 (COOH)(Ref. 0050)
Et ester-3,7-diacetate: nmaxcm-1: 1730 (C=O), 3530 (OH)(Ref. 0264)
1H-NMR (Pyridine-d5) d: 0.69 (3H, s, 18-CH3), 0.97 (3H, s, 19-CH3), 1.17 (3H, d, J=6Hz, 21-CH3), 3.4-4.4 (3H, m, 3b-, 7b- and 22-CH-OH)(Ref. 0050)
13C-NMR (CD3OD) d: C-1 36.5, C-2 31.4, C-3 72.9, C-4 40.6, C-5 43.1, C-6 35.9, C-7 69.1, C-8 40.8, C-9 34.0, C-10 36.1, C-11 21.7, C-12 40.8, C-13 43.9, C-14 51.2, C-15 24.7, C-16 28.4, C-17 54.6, C-18 12.1, C-19 23.4, C-20 43.1, C-21 12.8, C-22 71.2, C-23 36.5(Ref. 0004/0050)
Et ester-3,7-diacetate 1H-NMR (CD3OD) d: 18-Me 0.72(s), 19-Me 0.92(s), 21-Me 0.97(d), 3b-H 3.20-3.50(brm), 7b-H 3.70-3.85(m), 22-H 4.00-4.30(brm), 3-,7- and 22-OH and24-COOH 4.76(s)(Ref. 0264)
Et ester-3,7-diacetate 1H-NMR (CDCl3) d: 18-Me 0.67(s), 19-Me 0.90(s), CH2CH3 1.23(t, J, 6.0), 7a-OCOMe 1.94(s), 3a-OCOMe 1.97(s), 23-H2 2.13-2.33(m), 22-OH 2.50(brs), 22-H 3.83-4.17(m), CH2CH3 4.02(q, J, 6.0), 3b-H 4.20-4.60(brm), 7b-H 4.60-4.77(m)(Ref. 0264)
Me ester Hi-MS, m/z: M+, 422.3002 (CALCD. FOR C25H42O5=422.3030); M-H2O, 404.2945 (CALCD. FOR C25H40O4=404.2925); M-2H2O, 386.2729 (CALCD. FOR C25H38O3=386.2818)(Ref. 0050)







[0004] / [0050] / [0264]
101
Haemulcholic Acid
(22S)-3a,7a,22-Trihydroxy-5b-cholan-24-oic Acid
 BBA0101
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

247-250degC(Ref. 0050)
143-145degC (Et ester-3,7-diacetate)(Ref. 0264)
[a]D: +2.4deg (C=1.3, MeOH)(Ref. 0050)
nmax cm-1: 3400 (OH), 1720 (COOH)(Ref. 0050)
Et ester-3,7-diacetate: nmaxcm-1: 1730 (C=O), 3530 (OH)(Ref. 0264)
1H-NMR (Pyridine-d5) d: 0.74 (3H, s, 18-CH3), 0.96 (3H, s, 19-CH3), 1.16 (3H, d, J=6Hz, 21-CH3), 3.4-4.4 (3H, m, 3b-, 7b- and 22-CH-OH)(Ref. 0050)
13C-NMR (CD3OD) d: C-1 36.6, C-2 31.5, C-3 73.0, C-4 40.6, C-5 43.2, C-6 36.0, C-7 69.2, C-8 40.9, C-9 34.1, C-10 36.2, C-11 21.8, C-12 41.2, C-13 43.5, C-14 51.4, C-15 24.7, C-16 28.7, C-17 53.8, C-18 12.1, C-19 23.4, C-20 42.0, C-21 12.4, C-22 70.9, C-23 41.5(Ref. 0004/0050)
Et ester-3,7-diacetate 1H-NMR (CD3OD) d: 18-Me 0.68(s), 19-Me 0.92(s), 21-Me 0.95(d), 3b-H 3.17-3.50(brm), 7b-H 3.68-3.87(m), 22-H 3.97-4.27(m), 3-,7- and 22-OH and24-COOH 4.57(s)(Ref. 0264)
Et ester-3,7-diacetate 1H-NMR (CDCl3) d: 18-Me 0.63(s), 19-Me 0.90(s), CH2CH3 1.21(t, J, 6.0), 3a- and 7a-OCOMe 1.94(s), 23-H2 2.13-2.67(m), 22-OH 2.50(s), 22-H 3.83-4.10(m), CH2CH3 3.95(q, J, 6.0), 3b-H 4.14-4.57(brm), 7b-H 4.57-4.73(m)(Ref. 0264)
Me ester Hi-MS m/z: M+, 422.3070 (CALCD.FOR C25H42O5=422.3030); M-H2O, 404.2944 (CALCD.FOR C25H40O4=404.2925) ; M-2H2O, 386.2858 (CALCD.FOR C25H38O3=386.2818)(Ref. 0050)


Isolated from the bile of a marine teleost, Parapristipoma trilineatum, and fresh water fishes, Polypterus senegalus and Mormyrus caballus.(Ref. 0050/0051)
Isolated from seals, sealions and a walrus ; stereochemistry of a hydroxyl group at C-23 is unidentified.(Ref. 0100)
Primary bile acid in bony fish.(Ref. 0102)




[0004] / [0050] / [0051] / [0100] / [0102] / [0264]
102
Phocaecholic Acid
(23R)-3a,7a,23-Trihydroxy-5b-cholan-24-oic Acid
 BBA0102
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

225degC(Ref. 0053)
110-112degC (Me ester)(Ref. 0052)
[a]d-20: +21deg (C=1.06, EtOH)(Ref. 0053)
[a]d-23: +8deg (Me ester)(Ref. 0052)
M/D: +34deg (Me ester)(Ref. 0052)
Me ester: nmax cm-1: 1730 (C=O), 3500 (OH)(Ref. 0053/0054)
1H-NMR(CDCl3+DMSO-d6; 80MHz) d: 18-Me 0.69(s), 19-Me 0.98(s), 21-Me 0.97(d), 23-H 4.03(dd, J, 10.5 2.0)(Ref. 0054)
Me ester 1H-NMR(CDCl3+CD3OD) d: 18-Me 0.69(s), 19-Me 0.90(s), 21-Me 1.01(d), 3b-H 3.38(m), COOMe 3.78(s), 3timesOH 3.98(s), 23-H 4.24(m)(Ref. 0053/0054)
Me ester 13C-NMR(CDCl3+CD3OD) d: C20 32.30, C21 17.97, C22 41.50, C23 68.40, C24 176.50, C25 52.30(Ref. 0053)
Me ester (15eV) m/z: 422(M+, 7.6%), 404(M-18, 41.6%), 386 (M-2x18, 100%), 371(M-15-2x18, 40.1%), 332(M-18-ring A, 11.3%), 315(M-18-C23-C24, 13.0%), 297(M-2x18-C23-C24, 23.3%), 273(M-18-SC, 25.0%), 264(M-SC-C16-C17, 31.5%), 255(M-2x18-SC, 40.5%), 246(M-18-SC-C16-C17, 30.5%), 228(M-2x18-SC-C16-C17, 42.5%), 213(M-15-2x18-SC-C16-C17, 24.9%), 201(M-18-ring A-SC, 12.1%)(Ref. 0052)


Isolated from seal and walrus bile.(Ref. 0001/0101)
Isolated from duck bile.(Ref. 0054)
Primary bile acid in marine manmals and wading birds.(Ref. 0102)
Isolated from the biliary biles of flamingos and ducks.(Ref. 0165)
Isolated from the leopard seal, Hydrurga leptonyx, and the California sealion, Zalophus californianus.(Ref. 0168)




[0001] / [0052] / [0053] / [0054] / [0101] / [0102] / [0165] / [0168]
103
(23S)-3a,7a,23-Trihydroxy-5b-cholan-24-oic Acid
 BBA0103
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

215degC(Ref. 0053)
197-199degC (Me ester)(Ref. 0052)
[a]d-20: +15deg (C=1.0, EtOH)(Ref. 0053)
[a]d-23: +20deg (C=0.5, CHCl3) (Me ester)(Ref. 0052)
M/D: +84deg (Me ester)(Ref. 0052)
Me ester: nmax cm-1: 1730 (C=O), 3500 (OH)(Ref. 0053)
Me ester 1H-NMR(CDCl3+CD3OD) d: 18-Me 0.69(s), 19-Me 0.91(s), 21-Me 1.01(d), 3b-H 3.38(m), COOMe 3.76(s), 3timesOH 4.00(s), 23-H 4.24(m)(Ref. 0053/0054)
Me ester 13C-NMR(CDCl3+CD3OD) d: C-20 33.60, C-21 19.50, C-22 41.40, C-23 69.90, C-24 176.20, C-25 52.30(Ref. 0053)
Me ester (15eV) m/z: 422(M+, 10.8%), 404(M-18, 45.0%), 386(M-2x18, 100%), 371(M-15-2x18, 31.2%), 332(M-18-ring A, 8.5%), 315(M-18-C23-C24, 12.2%), 297(M-2x18-C23-C24, 21.8%), 273(M-18-SC, 27.7%), 264(M-SC-C16-C17, 33.1%), 255(M-2x18-SC, 35.9%), 246(M-18-SC-C16-C17, 26.1%), 228(M-2x18-SC-C16-C17, 34.0%), 213([M-15-2x18-SC-C16-C17, 21.1%), 201(M-18-ring A-SC, 9.5%)(Ref. 0052)


Primary bile acid in bony fish.(Ref. 0102)




[0052] / [0053] / [0054] / [0102]
104
3a,9a,11b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0104
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

203.6-204.0degC, (Me ester-3-acetate; mp, 166-167degC)(Ref. 0055)
[a]d-21: +58.3pm2deg (1.68%, MeOH), [a]d-20: +55.1deg (C=2.92, CHCl3) (Me ester-3-acetate)(Ref. 0055)









[0055]
105
Dehydrocholic Acid
3b,9a,11b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0105
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

171.0-172.3degC, (Me ester: mp, 147.7-148.8degC)<0055>>
[a]d-21: +35.5pm0.7deg (1.204%,CHCl3) (Me ester)(Ref. 0055)









[0055]
106
Dehydrocholic Acid
3,7,12-Trioxo-5b-cholan-24-oic Acid
 BBA0106
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

237degC(Ref. 0001)
[a]d-20: +26deg(Ref. 0001)
nmax m: 9.6-9.7, 9.91(Ref. 0003)
Me ester: nmax m: 9.68, 9.91(Ref. 0003)
Me ester 1H-NMR (CDCl3) d: 1.07 (3H, s, 18-CH3), 1.39 (3H, s, 19-CH3), 0.84 (3H, d, J=5Hz, 21-CH3), 3.63 (3H, s, COOCH3)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.2, C-2 36.4, C-3 208.6, C-4 42.7, C-5 46.7, C-6 44.9, C-7 208.4, C-8 49.0, C-9 45.7, C-10 36.0, C-11 38.6, C-12 211.6, C-13 56.9, C-14 51.8, C-15 25.1, C-16 27.5, C-17 45.6, C-18 11.7, C-19 21.8, C-20 35.4, C-21 18.5, C-22 31.3, C-23 30.4, C-24 174.3, C-25 51.3(Ref. 0004/0064)
Me ester (70eV) m/z: 416(M+, 90%), 398(M-H2O, 100%), 384(M-32, 9%), 380(M-2H2O, 3%), 367(M-H2O-31, 2%), 343(M-73, 18%), 301(M-SC, 30%), 283(M-H2O-SC, 33%), 275(M-SC-26, 7%), 274(M-SC-part of ring D (27), 18%), 265(M-2H2O-SC, 5%), 261(M-SC-40, 96%), 260(M-SC-41, 2%), 259(M-SC-ring D (42), 5%)(Ref. 0009)
The spectrum (70eV) was shown as the Me-ester derivative(Ref. 0007)







[0001] / [0003] / [0004] / [0005] / [0007] / [0009] / [0064]
107
Avicholic Acid
3a,7a,16a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0107
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

Me ester-3,7,16-triacetate 1H-NMR (CDCl3; 360MHz) d: 18-Me 0.702(s), 19-Me 0.928(s), 21-Me 0.948(d), -OCOMe 1.981(s),2.035(s) and 2.049(s), COOMe 3.649(s), 3b-H 4.591(m), 7b-H 4.817(bd, J, 2.5), 16b-H 4.939(bt, J, 6.0)(Ref. 0102/0103)



Primary bile acid in many birds.(Ref. 0102)
Isolated from biliary bile of herons (Ardeidae), pelicans (Pelecanidae), and owls (Tytonidae)(Ref. 0103)




[0102] / [0103]
108
3a,11a,15b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0108
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

153-155degC(Ref. 0056)
Me ester: nmax cm-1: 3408, 3380, 2934, 2863, 1723(Ref. 0056)
1H-NMR (CD3OD; 300MHz) d: 18-Me 0.95(s), 21-Me 0.98(d), 19-Me 1.08(s), 3b-H 3.57(m), 11b-H 3.79(td, J, 10.7, 4.2), 15a-H 4.14(td, J, 5.6, 0.9)(Ref. 0056)
Me ester 13C-NMR (25MHz) d: C-1 39.2, C-2 33.0, C-3 71.7, C-4 38.2, C-5 44.5, C-6 28.4, C-7 25.9, C-8 31.5, C-9 47.9, C-10 -, C11 68.6, C-12 54.0, C-13 -, C-14 60.7, C-15 69.0, C-16 42.4, C-17 56.9, C-18 16.4, C-19 24.4, C-20 35.9, C-21 18.8, C-22 31.5, C-23 31.5, C-24 - (Ref. 0056)
Molecular secondary ion mass spectrometry m/z: 431(M+Na)+, 415(M+Li)+(Ref. 0056)


A microbiological transformation product of litocholic acid by a fungus Cunninghamella blakesleeana ST-22.(Ref. 0056)




[0056]
109
3a,11b,15b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0109
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

236-237degC(Ref. 0056)
[a]d-25: +20.8deg (C=0.31, MeOH)(Ref. 0056)
nmax cm-1: 3422, 3402, 2929, 2863, 1711(Ref. 0056)
1H-NMR (CD3OD; 300MHz) d: 21-Me 0.97(d), 18-Me 1.13(s), 19-Me 1.20(s), 3b-H 3.55(m), 11a-H 4.10(td, J, 4.1, 2.5), 15a-H 4.18(td, J, 5.8, 0.8)(Ref. 0056)
Me ester 13C-NMR (25MHz) d: C-1 35.9, C-2 32.2, C-3 71.3, C-4 37.6, C-5 44.8, C-6 27.2, C-7 27.2, C-8 28.5, C-9 45.0, C-10 35.7, C-11 67.2, C-12 51.1, C-13 42.4, C-14 63.4, C-15 69.2, C-16 41.9, C-17 57.5, C-18 17.9, C-19 27.2, C-20 35.9, C-21 18.8, C-22 32.2, C-23 32.2, C-24 174.5(Ref. 0056)
Molecular secondary ion mass spectrometry m/z: 415(M+Li)+, 501(M+H+glycerol), 507(M+Li+glycerol)(Ref. 0056)


A microbiological transformation product of litocholic acid by a fungus Cunninghamella blakesleeana ST-22.(Ref. 0056)




[0056]
110
3a,12a,15a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0110
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

322-325degC (decomp.), (Me ester: mp, 257-259degC)(Ref. 0057/0058)
nmax cm-1: 3400, 1710(COOH)(Ref. 0058)
1H-NMR (Pyridine; 60MHz) d: 0.81 (3H, s, 18-CH3), 0.98 (3H, s, 19-CH3)(Ref. 0057/0058)
Me ester 1H-NMR (Pyridine-d5) d: 0.82 (3H, s, 18-CH3), 0.97 (3H, s, 19-CH3), 3.61 (3H, s, COOCH3), 3.85 (1H, m, 3b- H), 4,00-4.30 (2H, m, 12b- and 15b- H)(Ref. 0058)
Me ester m/z: 404 (M-H2O), 386 (M-2H2O), 368(M-3H2O), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC)(Ref. 0057/0058)







[0057] / [0058]
111
Pythocholic Acid
3a,12a,16a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0111
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

186-187degC, (Me ester: mp, 146-148degC)(Ref. 0059)
[a]d-23: +28pm1deg (C=1.2, CHCl3) (Me ester)(Ref. 0059)
Me ester-3,7,16-triacetate 1H-NMR(CDCl3; 360MHz) d: 18-Me 0.781(s), 21-Me 0.8.37(d), 19-Me 0.909(s), -OCOMe 2.032(s), 2.048(s), 2.169(s) and 3.650(s), 3b-H 4.701(m), 16b-H 4.908(bt, J, 7.2), 12b-H 5.035(bs)(Ref. 0102/0103)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Constituent of bile acid of boa and python.(Ref. 0059)
Isolated from certain primitive snakes, boas and pythons.(Ref. 0100)
Bile acid identified in snake.(Ref. 0102)
A main constituent of the bile of African python.(Ref. 0238)




[0007] / [0059] / [0100] / [0102] / [0103] / [0238]
112
3a,15b,18-Trihydroxy-5b-cholan-24-oic Acid
 BBA0112
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

191-192degC (Me ester)(Ref. 0056)
[a]d-15: +10.2deg (C=0.46, MeOH) (Me ester)(Ref. 0056)
Me ester: nmax cm-1: 3283, 3251, 2936, 2863, 1739(Ref. 0056)
Me ester 1H-NMR (CD3OD; 300MHz) d: 19-Me 0.93(s), 21-Me 0.98(d), 3b-H 3.63(m), COOMe 3.65(s), 15a-H 4.24(td, J, 6.5, 1.4)(Ref. 0056)
Me ester 13C-NMR (25MHz) d: C-1 36.1, C-2 31.2, C-3 71.1, C-4 37.5, C-5 42.6, C-6 27.7, C-7 25.8, C-8 32.3, C-9 41.4, C-10 35.1, C-11 21.6, C-12 38.9, C-13 47.3, C-14 60.6, C-15 69.1, C-16 42.7, C-17 56.4, C-18 61.8, C-19 23.5, C-20 34.9, C-21 19.5, C-22 31.5, C-23 31.7, C-24 174.5,C-25 51.3(Ref. 0056)
Molecular secondary ion mass spectrometry Me ester m/z: 423(M+H)+(Ref. 0056)


A biotransformation product of litocholic acid by fungus Cunninghamella blakesleeana ST-22.(Ref. 0056)




[0056]
113
Bitocholic Acid
(23R)-3a,12a,23-Trihydroxy-5b-cholan-24-oic Acid
 BBA0113
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

230-232degC, (Me ester: mp, 119-120degC)(Ref. 0053)
[a]d-20: +48deg (C=0.856, EtOH), [a]d-20: +44.2deg (C=0.34, EtOH) (Me ester)(Ref. 0053)
Me ester: nmaxcm-1: 1730(C=O), 3500(OH)(Ref. 0053)
Me ester 1H-NMR (CDCl3+CD3OD) d: 18-Me 0.71(s), 19-Me 0.91(s), 21-Me 1.10(d), 3b-H and 3timesOH 3.45(m), COOMe 3.81(s), 12b-H 4.05(m), 23-H 4.28(m)(Ref. 0053)
Me ester 13C-NMR (CDCl3+CD3OD) d: C-20 32.37, C-21 17.08, C-22 40.88, C-23 68.43, C-24 176.69, C-25 52.36(Ref. 0053)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from the bile of certain snakes, especially of the Gaboon viper, Bitis gabonica Viperidae and puff adder, Bitis arietans.(Ref. 0001/0101/0168)
Isolated from snake bile ; identified in the European adder Vipera kerus ; stereochemistry of a hydroxyl group at C-23 is unidentified.(Ref. 0100)
A bacterial 7-dehydroxylation product of (23R)-3a,7a,12a,23+tetrahydroxy-5b-cholan-24-oic acid.(Ref. 0102)
Isolated from snakes of the subfamily Viperinae ; A biotransformation product of deoxycholic acid in the adder (Vipera berus; Linn.) liver.(Ref. 0175)




[0001] / [0007] / [0053] / [0100] / [0101] / [0102] / [0168] / [0175]
114
1b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0114
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

288-290degC(Ref. 0016)
Me ester 1H-NMR (pyridine-d5; 90MHz) d: 18-Me 0.81(s), 19-Me 1.40(s), 1a-, 7b- and 12b-H 4.03-4.38(m), 3b-H 4.48-4.86(m)(Ref. 0016)
Me ester 13C-NMR (CD3OD; 100.6MHz) d: C-1 74.1, C-2 38.0, C-3 67.3, C-4 40.0, C-5 37.0, C-6 35.5, C7 68.8, C-8 41.3, C-9 29.5, C-10 40.3, C-11 29.6, C-12 73.8, C-13 47.3, C-14 42.9, C-15 24.3, C-16 28.5, C-17 48.0, C-18 13.0, C-19 17.9, C-20 36.8, C-21 17.6, C-22 32.2, C-23 31.8, C-24 176.4(Ref. 0004/0141)
Me-TMS ether (70eV) m/z: 636(M-2TMSOH), 456(M-3TMSOH, 17%), 366(M-4TMSOH, 18%), 251(M-4TMSOH-SC, 11%), 217(100%)(Ref. 0007/0016)


Detected in human meconium.(Ref. 0016)
Isolated from human urine, serum, faeces, and meconium of patients suffering intrahepatic cholestasis.(Ref. 0141)
Identified in human meconium. : stereochemistry of hydroxyl groups is unidentified.(Ref. 0148/0149/0176/0186/0200/0201)
A hydroxyation metabolite of deoxycholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Fetal bile acid in urine, meconium, and feces.(Ref. 0180)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Detected in serum and urine from healthy human adults.(Ref. 0189)
Fetal bile acid identified in a dried blood disc, meconium and urine.(Ref. 0190)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Excreted in urine of healthy newborn.(Ref. 0194/0210)
Isolated from human fetal gallbladder bile.(Ref. 0198)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in urine of newborns.(Ref. 0245)




[0004] / [0007] / [0016] / [0141] / [0148] / [0149] / [0153] / [0176] / [0180] / [0186] / [0188] / [0189] / [0190] / [0192] / [0194] / [0198] / [0199] / [0200] / [0201] / [0202] / [0210] / [0245]
115
2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0115
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

230-232degC, (Me ester; mp, 197-199degC)(Ref. 0015)
[a]d-18: +27.2pm2deg (C=1.03, EtOH)(Ref. 0218)
nmaxcm-1: 1702(C=O), 3436, 978(OH)(Ref. 0015)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.90(s), 21-Me 0.99(d), 2a- and 3b-H 3.40(brm), 7b-H 3.88(m), 12b-H 4.03(m)(Ref. 0015)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.63(s), 19-Me 0.88(s), 21-Me 0.93(d), 3b-H 3.24(brm), 2a-H 3.58(brm), COOMe 3.63(s), 7b-H 3.79(m), 12b-H 3.92(m)(Ref. 0015)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 43.14, C-2 70.55, C-3 76.54, C-4 37.26, C-5 41.39, C-6 33.87, C-7 68.33, C-8 39.46, C-9 27.67, C-10 37.16, C-11 28.43, C-12 72.99, C-13 46.44, C-14 41.64, C-15 23.22, C-16 27.62, C-17 47.03, C-18 12.50, C-19 22.43, C-20 35.48, C-21 17.34, C-22 31.29, C-23 31.04, C-24 174.86, C-25 51.54(Ref. 0015)
1H-NMR (C5D5N; 100MHz) d: 18-Me 0.76(s), 19-Me 1.01(s), 21-Me 1.19(d), 2a-H 4.0-4.4(bm), 3b-H 3.5-3.9(bm), 7b-H 4.05(m), 12b-H 4.19(m)(Ref. 0218)
Me ester-2,3,7,12-tetraacetate 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.72(s), 19-Me 0.94(s), 21-Me 0.81(d), 2b-, 3a-, 7a- and 12a-OCOMe 1.97, 2.01, 2.05, 2.14(s), 2a- and 3b-H 4.5-5.2(bm), 7b-H 4.89(m), 12b-H 5.10(t, J, 6.0)(Ref. 0218)
(70eV) m/z: 424(M+), 406(M-H2O), 388(M-2H2O), 370(M-3H2O), 352(M-4H2O), 305(M-H2O-SC), 287(M-2H2O-SC), 269(M-3H2O-SC), 251(M-4H2O-SC)(Ref. 0218)
Me-TMS ether (20eV) m/z: 636(M-TMSOH), 546(M-2TMSOH), 456(M-3TMSOH), 367(M-3TMSOH-TMSO, 100%), 341(M-3TMSOH-SC), 243(Ref. 0007/0015)


Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Identified in urine of newborns.(Ref. 0245)




[0007] / [0015] / [0155] / [0188] / [0218] / [0245]
116
3a,4b,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0116
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

150-152degC, (Me ester; mp, 146-148degC)(Ref. 0017)
nmaxcm-1: 1703(C=O), 3396, 1028(OH)(Ref. 0017)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 19-Me 0.91(s), 21-Me 0.99(d), 3b-H 3.20(brm), 7b- and 12b-H 3.85(m), 4a-H 4.13(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.65(s), 19-Me 0.90(s), 21-Me 0.95(d), 3b-H 3.25(brm), COOMe 3.64(s), 7b-H 3.88(m), 12b-H 3.94(t, J, 2.8), 4a-H 4.12(dd, J, 10.7, 9.1)(Ref. 0017)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.6, C-2 28.1, C-3 76.0, C-4 75.3, C-5 47.9, C-6 27.5, C-7 68.5, C-8 39.2, C-9 28.1, C-10 36.8, C-11 28.1, C-12 73.0, C-13 46.4, C-14 41.6, C-15 23.1, C-16 27.5, C-17 47.0, C-18 12.4, C-19 22.5, C-20 35.2, C-21 17.3, C-22 31.0, C-23 31.0, C-24 174.7, C-25 51.4(Ref. 0017)
Me ester (60eV) m/z: 420(M-H2O, 4%), 402(M-2H2O, 21%), 384(M-3H2O, 25%), 287(M-2H2O-SC, 35%), 269(M-3H2O-SC, 100%), 260(M-2H2O-SC-part of ring D (27), 12%), 242(M-3H2O-SC-27, 32%), 127(25%)(Ref. 0017)


Isolated from feces from healthy newborn infants.(Ref. 0159)
Identified in human urine.(Ref. 0163)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in urine of newborns.(Ref. 0245)




[0017] / [0159] / [0163] / [0188] / [0192] / [0202] / [0245]
117
3b,4b,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0117
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

148-149degC, (Me ester; mp, 216-218degC)(Ref. 0017)
nmaxcm-1: 1708(C=O), 3385, 1023(OH)(Ref. 0017)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.94(s), 21-Me 0.98(d), 3a-, 7b- and 12b-H 3.93(m), 4a-H 4.36(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.68(s), 19-Me 0.93(s), 21-Me 0.95(d), COOMe 3.64(s), 7b-H 3.90(m), 3a-H 3.94(m), 12b-H 3.97(t, J, 2.9), 4a-H 4.36(dd, J, 11.0, 3.3)(Ref. 0017)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.2, C-2 25.6, C-3 69.7, C-4 71.1, C-5 42.7, C-6 28.6, C-7 68.9, C-8 39.4, C-9 27.4, C-10 36.6, C-11 28.0, C-12 73.1, C-13 46.4, C-14 41.8, C-15 23.2, C-16 27.4, C-17 47.2, C-18 12.5, C-19 22.6, C-20 35.2, C-21 17.3, C-22 31.1, C-23 30.9, C-24 174.7, C-25 51.4(Ref. 0017)
Me ester (60eV) m/z: 420(M-H2O, 29%), 402(M-2H2O, 65%), 384(M-3H2O, 24%), 287(M-2H2O-SC, 100%), 269(M-3H2O-SC, 44%), 260(M-2H2O-SC-part of ring D (27), 54%), 242(M-3H2O-SC-27, 14%), 263(M-H2O-SC-ring D (42), 2%), 245(M-2H2O-SC-42, 3%), 127(62%)(Ref. 0017)
Me-DMES ether (70eV) m/z: 753(M-29), 678(M-DMESOH), 574(M-2DMESOH), 470(M-3DMESOH), 367(M-4DMESOH), 251(M-SC-4DMESOH), 299, 195, 429, 327(Ref. 0060)


Identified in healthy neonatal urine.(Ref. 0060)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)




[0017] / [0060] / [0202]
118
3a,6a,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0118
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

158-161degC(Ref. 0034)
[a]d-26: +23.3deg (C=0.47, MeOH)(Ref. 0181)
nmaxcm-1: 1710(C=O), 3419, 1040 (OH)(Ref. 0034)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.88(s), 21-Me 0.99(d), 3b-H 3.42(brm), 6b-H 3.77(brm), 7b-H 3.77(m), 12b-H 3.91(m)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.67(s), 19-Me 0.89(s), 21-Me 0.98(d), 3b-H 3.41(brm), COOMe 3.66(s), 6b-H 3.81(m), 7b-H 3.85(m), 12b-H 3.96(m)(Ref. 0034/0035)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.64, C-2 29.86, C-3 71.70, C-4 32.22, C-5 47.79, C-6 69.99, C-7 72.04, C-8 38.62, C-9 26.22, C-10 35.71, C-11 28.16, C-12 72.98, C-13 46.56, C-14 41.61, C-15 23.20, C-16 27.57, C-17 47.03, C-18 12.49, C-19 22.78, C-20 35.38, C-21 17.33, C-22 30.95, C-23 31.15, C-24 174.92, C-25 51.58(Ref. 0034/0035/0141)
Me ester (70eV) m/z: 438(M+, 1%), 420(M-H2O, 3%), 402(M-2H2O, 25%), 384(M-3H2O, 52%), 366(M-4H2O, 10%), 305(M-H2O-SC, 35%), 287(M-2H2O-SC, 31%), 269(M-3H2O-SC, 70%), 251(M-4H2O-SC, 24%)(Ref. 0034)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Identified in amniotic fluid, serum, faeces, and urine from adult patients with cholestatic liver disease.(Ref. 0061/0141/0163/0176/0200)
A hydroxyation metabolite of cholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in human meconium and neonatal urine.(Ref. 0181)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Fetal bile acid identified in a dried blood disc, meconium and urine.(Ref. 0190)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Identified in urine, bile, portal and peripheral renous sera, and liver specimens from subjects with liver diseases (cholestasis, liver cirrhosis, chronic hepatitis, acute hepatitis).(Ref. 0201)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Identified in urine of infants during the first year.(Ref. 0210)
Identified in urine of newborns.(Ref. 0245)




[0007] / [0034] / [0035] / [0061] / [0141] / [0153] / [0155] / [0163] / [0176] / [0181] / [0188] / [0190] / [0192] / [0200] / [0201] / [0202] / [0210] / [0245]
119
3a,6a,7b,12a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0119
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

148-151degC, (Me ester; mp, 100-102degC)(Ref. 0034)
nmaxcm-1: 1708(C=O), 3421, 1040, 952 (OH)(Ref. 0034)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.90(s), 21-Me 0.98(d), 3b- and 7b-H 3.34(brm), 6a-H 3.60(brm), 12b-H 3.87(m)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.70(s), 19-Me 0.95(s), 21-Me 0.98(d), 7a-H 3.45(t, J, 9.6), 3b-H 3.57(brm), COOMe 3.67(s), 6b-H 3.78(dd, J, 9.6, 5.2), 12b-H 3.99(t, J, 4.3)(Ref. 0034/0035)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.38, C-2 29.72, C-3 71.28, C-4 30.45, C-5 47.82, C-6 73.28, C-7 75.25, C-8 41.82, C-9 32.15, C-10 34.97, C11 28.90, C12 72.52, C-13 47.53, C-14 45.98, C-15 26.36, C-16 27.99, C-17 47.42, C-18 12.89, C-19 23.40, C-20 35.24, C-21 17.38, C-22 31.04, C-23 31.21, C-24 174.97, C-25 51.62(Ref. 0034/0035)
Me ester (70eV) m/z: 402(M-2H2O, 24%), 384(M-3H2O, 26%), 366(M-4H2O, 6%), 305(M-H2O-SC, 69%), 287(M-2H2O-SC, 35%), 269(M-3H2O-SC, 82%), 251(M-4H2O-SC, 22%)(Ref. 0034)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0007] / [0034] / [0035]
120
3a,6b,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0120
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

154-157degC(Ref. 0034)
[a]d-26: +36.3deg (C=0.52, MeOH)(Ref. 0181)
nmaxcm-1: 1748, 1703(C=O), 3538, 1014, 986, 952 (OH)(Ref. 0034)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.70(s), 21-Me 1.00(d), 19-Me 1.06(s), 3b-H 3.39(brm), 6a- and 7b-H 3.66(m), 12b-H 3.92(m)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.72(s), 19-Me 1.06(s), 21-Me 0.98(d), 3b-H 3.49(brm), COOMe 3.67(s), 6a-H 3.70(m), 7b-H 75(m), 12b-H 4.00(m)(Ref. 0034/0035)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.82, C-2 29.68, C-3 71.40, C-4 36.08, C-5 47.45, C-6 76.02, C-7 72.99, C-8 34.98, C-9 26.51, C-10 34.56, C-11 27.96, C-12 73.31, C-13 46.42, C-14 41.13, C-15 23.28, C-16 27.63, C-17 47.07, C-18 12.51, C-19 24.78, C-20 35.39, C-21 17.36, C-22 31.01, C-23 31.16, C-24 175.09, C-25 51.65(Ref. 0034/0035/0141)
Me ester (70eV) m/z: 420(M-H2O, 6%), 402(M-2H2O, 33%), 384(M-3H2O, 24%), 366(M-4H2O, 4%), 305(M-H2O-SC, 23%), 287(M-2H2O-SC, 50%), 269(M-3H2O-SC, 46%), 251(M-4H2O-SC, 15%)(Ref. 0034)
Me-TMS ether (70eV) m/z: 636(M-TMSOH, 24%), 546(M-2TMSOH, 85%), 531(M-2TMSOH-CH3, 9%), 456(M-3TMSOH, 72%), 441(M-3TMSOH-CH3, 28%), 431(M-2TMSOH-SC, 30%),365(M-4TMSOH-H, 36%), 341(M-3TMSOH-SC, 100%), 251(M-4TMSOH-SC, 51%)(Ref. 0061)


Identified in amniotic fluid and urine from adult patients with cholestatic liver disease.(Ref. 0061/0141)
Hydroxyation metabolite of cholic acid in urine of a patient with intrahepatic cholestasis.(Ref. 0153)




[0034] / [0035] / [0061] / [0141] / [0153] / [0181]
121
3a,6b,7b,12a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0121
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

234-236degC, (Me ester; mp, 173-174degC)(Ref. 0034)
[a]d-26: +68.5deg (C=0.64, MeOH)(Ref. 0181)
nmaxcm-1: 1716(C=O), 3366, 1001 (OH)(Ref. 0034)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 21-Me 0.98(d), 19-Me 1.04(s), 3b- and 7a-H 3.39(brm), 6a-H 3.54(m), 12b-H 3.89(m)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.73(s), 19-Me 1.09(s), 21-Me 0.99(d), 3b- and 7a-H 3.60(brm), COOMe 3.67(s), 6a-H 3.70(m), 12b-H 4.00(m)(Ref. 0034/0035)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.56, C-2 30.04, C-3 71.09, C-4 35.62, C-5 47.31, C-6 75.74, C-7 73.54, C-8 38.85, C-9 32.85, C-10 33.53, C-11 28.75, C-12 72.55, C-13 47.60, C-14 46.30, C-15 26.64, C-16 27.92, C-17 47.48, C-18 12.92, C-19 22.25, C-20 35.09, C-21 17.59, C-22 31.13, C-23 31.24, C-24 174.69, C-25 51.50(Ref. 0034/0035)
Me ester (70eV) m/z: 420(M-H2O, 22%), 402(M-2H2O, 29%), 384(M-3H2O, 15%), 305(M-H2O-SC, 60%), 287(M-2H2O-SC, 39%), 269(M-3H2O-SC, 82%), 251(M-4H2O-SC, 22%)(Ref. 0034)
Me-TMS ether (70eV) m/z: 636(M-TMSOH, 3%), 546(M-2TMSOH, 21%), 531(M-2TMSOH-CH3, 15%), 456(M-3TMSOH, 34%), 441(M-3TMSOH-CH3, 15%), 431(M-2TMSOH-SC, 14%), 366(M-4TMSOH, 13%), 341(M-3TMSOH-SC, 43%), 285(ring A+19-CH3+6-CHOTMS, 100%), 251(M-SC-360, 23%), 195(285-TMSOH, 87%)(Ref. 0061)


Identified in amniotic fluid and urine from adult patients with cholestatic liver disease.(Ref. 0061/0141)




[0034] / [0035] / [0061] / [0141] / [0181]
122
3a,6b,7a,12b-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0122
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

168-170degC(Ref. 0062)
[a]d-25: +30.2deg (C=0.58)(Ref. 0062)
nmaxcm-1: 1717 (C=O), 3410, 998 (OH)(Ref. 0062)
1H-NMR (CDCl3+DMSO-d6; 400MHz) d: 18-Me 0.76(s), 21-Me 1.02(d, J=5.6Hz), 19-Me 1.08(s), 3b- and 12b-H 3.39(brm), 6a- and 7b-H 3.67(m)(Ref. 0062)
Me-TMS ether (70eV) m/z: 711(M-15), 636(M-TMSOH, 1.1%), 546(M-2TMSOH, 4.0%), 456(M-3TMSOH, 10.9%), 366(M-4TMSOH, 5.1%), 431(4.6%), 341(15.8%), 285(74.5%), 251(10.3%), 195(100%)(Ref. 0062)







[0062]
123
3a,6b,7b,12b-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0123
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

204-206degC(Ref. 0062)
[a]d-25: +60.3deg (C=0.74)(Ref. 0062)
nmaxcm-1: 1718 (C=O), 3410, 1005 (OH)(Ref. 0062)
1H-NMR (CDCl3+DMSO-d6; 400MHz) d: Me-18 0.74(s), 21-Me 1.00(d, J=5.6Hz), 19-Me 1.07(s), 3a-,7b- and 12b-H 3.39(brm), 6a-H 3.55(m)(Ref. 0062)
Me-TMS ether (70eV) m/z: 711(M-15, 0.4%), 636(M-TMSOH, 1.1%), 546(M-2TMSOH, 4.0%), 456(M-3TMSOH, 10.9%), 366(M-4TMSOH, 5.1%), 431(4.6%), 341(15.8%), 285(74.5%), 251(10.3%), 195(100%)(Ref. 0062)







[0062]
124
3a,6a,7b,12a-Tetrahydroxy-5a-cholan-24-oic Acid
 BBA0124
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

152-155degC, (Me ester; mp, 155-156degC)(Ref. 0037)
nmaxcm-1: 1705 (C=O), 3430, 1012, 988 (OH)(Ref. 0037)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.78(s), 21-Me 0.99(d), 6b- and 7a-H 3.07(brm), 12b-H 3.91(m), 3b-H 3.99(m)(Ref. 0035/0037)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.665(s), 19-Me 0.770(s), 21-Me 0.944(d), 6b-H 3.117(brm), 7a-H 3.163(brm), COOMe 3.630(s), 12b-H 3.951(brs), 3b-H 4.072(brs)(Ref. 0035/0037)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 32.48, C-2 28.29, C-3 65.76, C-4 30.06, C-5 42.20, C-6 75.31, C-7 80.62, C-8 41.02, C-9 44.83, C-10 35.80, C-11 28.29, C-12 72.49, C-13 47.25, C-14 46.07, C-15 26.42, C-16 27.95, C-17 47.68, C-18 12.89, C-19 12.37, C-20 35.18, C-21 17.39, C-22 31.03, C-23 31.19, C-24 174.89, C-25 51.61(Ref. 0035/0037)
Me ester (70eV) m/z: 420(M-H2O, 3%), 402(M-2H2O, 27%), 384(M-3H2O, 13%), 305(M-H2O-SC, 100%), 287(M-2H2O-SC, 40%), 269(M-3H2O-SC, 58%), 251(M-4H2O-SC, 13%)(Ref. 0037)







[0035] / [0037]
125
3a,6b,7b,12a-Tetrahydroxy-5a-cholan-24-oic Acid
 BBA0125
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

235-237degC, (Me ester; mp, 151-152degC)(Ref. 0037)
nmaxcm-1: 1698 (C=O), 3525, 1033, 1014 (OH)(Ref. 0037)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 19-Me 0.93(s), 21-Me 0.99(d), 7a-H 3.25(brm), 6a-H 3.51(m), 12b-H 3.92(m), 3b-H 4.06(m)(Ref. 0035/0037)
Me ester 1H-NMR(CDCl3; 500MHz) d: 18-Me 0.696(s), 19-Me 0.937(s), 21-Me 0.952(d), 7a-H 3.342(dd, J, 3.4, 9.0), 6a-H 3.584(t, J, 2.5), COOMe 3.633(s), 12b-H 3.964(t. J, 2.5), 3b-H 4.123(t, J, 1.8)(Ref. 0035/0037)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 32.95, C-2 29.04, C-3 66.45, C-4 34.06, C-5 40.38, C-6 75.02, C-7 76.58, C-8 38.23, C-9 45.33, C-10 35.03, C-11 28.13, C-12 72.55, C-13 47.39, C-14 46.15, C-15 26.72, C-16 27.98, C-17 47.13, C-18 12.90, C-19 14.81, C-20 35.14, C-21 17.48, C-22 31.00, C-23 31.18, C-24 174.86, C-25 51.61(Ref. 0035/0037)
Me ester (70eV) m/z: 420(M-H2O, 2%), 402(M-2H2O, 16%), 384(M-3H2O, 10%), 305(M-H2O-SC, 100%), 287(M-2H2O-SC, 57%), 269(M-3H2O-SC, 91%), 251(M-4H2O-SC, 18%)(Ref. 0037)







[0035] / [0037]
126
3a,7a,12a,19-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0126
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

275-277degC(Ref. 0128)
[a]d-20: +40.4deg (C=0.95, MeOH)(Ref. 0128)
nmaxcm-1: 3450, 2650, 1700(Ref. 0128)
1H-NMR (Pyridine-d5; 400MHz) d: 18-Me 0.84(s), 19-H2 3.93 and 4.28(d, J=11Hz), 21-Me 1.24(d, J=6Hz), 3b-H 3.89(m), 7b-H 4.16(brs), 12b-H 4.27(brs)(Ref. 0128)
Me-DMES ether (70eV) m/z: 561(M-DMESOH-117), 457(M-2DMESOH-117), 353(M-3DMESOH-117), 753(M-C2H5), 470(M-3DMESOH), 367(M-3DMESOH-DMESO), 251(M-4DMESOH-SC)(Ref. 0128)


Occurred in human neonatal urine.(Ref. 0128)




[0128]
127
Dehydrolithocholic Acid
3-Oxo-5b-cholan-24-oic Acid
 BBA0127
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

138-139degC, (Me ester; mp, 119-120degC)(Ref. 0001)
[a]D: +33deg (dioxane)(Ref. 0002)
Me ester: lmax (EtOH) (loge): 285(19) nm(Ref. 0263)
nmaxcm-1: 1745, 1720(Ref. 0093)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 21-Me 0.92(d), 19-Me 1.01(s)(Ref. 0005/0093)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.1, C-2 36.9, C-3 212.9, C-4 42.3, C-5 44.3, C-6 25.7, C-7 26.6, C-8 35.6, C-9 40.9, C-10 34.9, C-11 21.1, C-12 40.1, C-13 42.8, C-14 56.9, C-15 24.1, C-16 28.1, C-17 56.0, C-18 12.0, C-19 22.6, C-20 35.2, C-21 18.2, C-22 31.0, C-23 31.0, C-24 179.5, C-25 51.3(Ref. 0004/0064/0140)
Me ester (70eV) m/z: 388(M+, 100%), 373(M-CH3, 22%), 370(M-H2O, 9%), 357(M-31, 20%), 356(M-32, 45%), 355(M-H2O-CH3, 19%), 318(34%), 317(M-71, 5%), 315(M-73, 33%), 273(M-SC, 70%), 271(M-117, 23%), 262(24%), 255(M-H2O-SC, 19%), 246(M-SC-part of ring D (27), 37%), 233(M-SC-40, 10%), 231(M-SC-ring D (42), 47%), 178(8%)(Ref. 0009)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)


Detected in human feces.(Ref. 0101/0161/0205)
Identified in human serum.(Ref. 0160)




[0001] / [0002] / [0004] / [0005] / [0007] / [0009] / [0064] / [0093] / [0101] / [0140] / [0160] / [0161] / [0205] / [0263]
128
3-Oxo-5a-cholan-24-oic Acid
 BBA0128
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

183-184degC, (Me ester; mp, 113-114degC)(Ref. 0013/0237)
[a]D: +32.6pm0.5deg (C=0.98, MeOH)(Ref. 0013/0237)
[a]D: +40.5deg (Me ester)(Ref. 0237)
Me ester: nmaxcm-1: 1739, 1715, 1228, 985(Ref. 0013)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.92(s), 21-Me 1.01(d)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 38.5, C-2 38.0, C-3 221.6, C-4 44.6, C-5 46.6, C-6 28.9, C-7 31.6, C-8 35.3, C-9 53.7, C-10 35.5, C-11 21.3, C-12 39.8, C-13 42.6, C-14 56.2, C-15 24.1, C-16 28.0, C-17 55.9, C-18 12.0, C-19 11.4, C-20 35.3, C-21 18.2, C-22 30.9, C23 30.9, C-24 174.5, C-25 51.3(Ref. 0065)
Me ester (70eV) m/z: 388(M+, 39%), 373(M-CH3, 20%), 370(M-H2O, 4%), 357(M-31, 9%), 356(M-32, 14%), 355(M-H2O-CH3, 5%), 318(7%), 317(M-71, 3%), 315(M-73, 7%), 273(M-SC, 4%), 271(M-117, 4%), 262(3%), 255(M-H2O-SC, 3%), 246(M-SC-part of ring D (27), 35%), 233(M-SC-40, 16%), 231(M-SC-ring D (42), 100%), 178(3%)(Ref. 0009)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)


Detected in human faeces.(Ref. 0101/0205)




[0007] / [0008] / [0009] / [0013] / [0065] / [0101] / [0205] / [0237]
129
6-Oxo-5b-cholan-24-oic Acid
 BBA0129
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

142-146degC(Ref. 0043)
as Me ester; mp, 116-118degC(Ref. 0019)
[a]D: -41.5deg (dioxane)(Ref. 0043)
[a]D: -39.4deg (dioxane) (Me ester)(Ref. 0001)
nmaxcm-1: 1736 (C=O)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.83(s), 21-Me 0.93(d), COOMe 3.66(s)(Ref. 0019)
Me ester (70eV) m/z: 388(M+, 85%), 373(M-CH3, 48%), 370(M-H2O, 6%), 357(M-31, 10%), 356(M-32, 5%), 355(M-H2O-CH3, 4%), 333(M-55, 100%), 317(M-71, 1%), 315(M-73, 35%), 292(2%), 273(M-SC, 21%), 271(M-117, 2%), 255(M-H2O-SC, 8%), 246(M-SC-part of ring D (27), 18%), 233(M-SC-40, 6%), 231(M-SC-ring D (42), 47%), 178(5%)(Ref. 0009)







[0001] / [0009] / [0019] / [0043]
130
6-Oxo-5a-cholan-24-oic Acid
 BBA0130
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

162-164degC, (Me ester; mp, 85-87degC)(Ref. 0019/0237)
[a]d-20: -3.5pm3deg (C=0.6, dioxane)(Ref. 0074/0237)
nmaxcm-1: 1710 (C=O)(Ref. 0019)
1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.72(s), 21-Me 0.94(d)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.73(s), 21-Me 0.93(d), COOMe 3.66(s)(Ref. 0019)








[0019] / [0074] / [0237]
131
7-Oxo-5b-cholan-24-oic Acid
 BBA0131
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

150-151degC, (Me ester; mp, 92-93degC)(Ref. 0001)
nmaxcm-1: 1700-1730(Ref. 0063)
1H-NMR (CDCl3) d: 18-Me 0.67 (s), 19-Me 1.19 (s)(Ref. 0063)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.66 (s), 19-Me 1.18 (s), COOMe 3.65(s)(Ref. 0005/0063)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.4, C-2 21.6, C-3 26.5, C-4 28.1, C-5 47.6, C-6 45.8, C-7 212.2, C-8 49.5, C-9 42.8, C-10 35.8, C-11 20.6, C-12 39.0, C-13 42.8, C-14 49.0, C-15 24.8, C-16 28.1, C-17 54.8, C-18 12.0, C-19 23.8, C-20 35.2, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.4, C-25 51.3(Ref. 0004/0064)
Me ester (22eV) m/z: 388(M+, 50%), 370(M-H2O, 21%), 356(M-CH3OH, 50%), 355(M-CH3-H2O, 16%), 341(M-CH3OH-CH3, 10%), 339(M-CH3O-H2O, 16%), 323(M-CH3OH-H2O-CH3, 12%), 315(M-part of SC, 97%), 297(315-H2O, 10%), 292(M-ring A, 100%), 273(M-SC, 35%), 170(M-SC-ring A, 30%), 255(M-H2O-SC, 75%), 115(SC fragment, 12%), 74(SC fragment, 20%)(Ref. 0009/0039)







[0001] / [0004] / [0005] / [0009] / [0039] / [0063] / [0064]
132
12-Oxo-5b-cholan-24-oic Acid
 BBA0132
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

184.5-187degC, (Me ester; mp, 112-113degC)(Ref. 0063)
[a]D: +95deg (C=0.1, MeOH), [a]D: 101deg (C=0.1, MeOH) (Me ester)(Ref. 0001)
nmaxcm-1: 1720, 1700(Ref. 0063)
1H-NMR (CDCl3) d: 18-Me 1.12(s), 19-Me 1.07(s)(Ref. 0063)
Me ester 1H-NMR (CDCl3) d: 18- and 19-Me 1.03(s), COOMe 3.70(s)(Ref. 0005/0063)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.0, C-3 26.9, C-4 27.4, C-5 43.1, C-6 26.9, C-7 26.2, C-8 35.8, C-9 44.3, C-10 36.2, C-11 38.1, C-12 214.9, C-13 57.5, C-14 58.7, C-15 24.3, C-16 27.4, C-17 46.5, C-18 11.6, C-19 23.6, C-20 35.6, C-21 18.5, C-22 31.3, C-23 30.5, C-24 174.5, C-25 51.2(Ref. 0004/0064)
Me ester (22eV) m/z: 388(M+), 273, 233 (Base peak)(Ref. 0009/0063)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)







[0001] / [0004] / [0005] / [0007] / [0009] / [0063] / [0064]
133
12-Oxo-5a-cholan-24-oic Acid
 BBA0133
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

184-186degC(Ref. 0001)
112.5-114.0degC (Me ester)(Ref. 0014)
[a]d-20: +108deg (C=2, CHCl3)(Ref. 0001)
Me ester: nmaxcm-1: 1703, 1743 (C=O)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.86(d), 18-Me 0.89(s), 19-Me 1.02(s), COOMe 3.65(s)(Ref. 0008/0014)
13C-NMR (CDCl3; 22.53MHz) d: C-1 38.3, C-2 21.9, C-3 26.5, C-4 28.8, C-5 46.9, C-6 28.8, C-7 31.5, C-8 35.7, C-9 57.8, C-10 37.7, C-11 38.3, C-12 215.2, C-13 57.2, C-14 58.6, C-15 24.3, C-16 27.4, C-17 46.4, C-18 11.7, C-19 11.9, C-20 35.3, C-21 18.6, C-22 31.3, C-23 30.6, C-24 174.6, C-25 51.4(Ref. 0065)
Me ester (70eV) m/z: 388(M+, 69%), 373(M-CH3, 1%), 370(M-H2O, 6%), 357(M-31, 3%), 356(M-32, 1%), 355(M-H2O-CH3, 2%), 333(M-55, 3%), 315(M-73, 1%), 273(M-SC, 15%), 271(M-117, 4%), 255(M-H2O-SC, 9%), 246(M-SC-part of ring D (27), 4%), 233(M-SC-40, 100%), 231(M-SC-ring D (42), 5%)(Ref. 0009)







[0001] / [0008] / [0009] / [0014] / [0065]
134
3,6-Dioxo-5b-cholan-24-oic Acid
 BBA0134
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

210degC, (Me ester; mp, 128-129degC)(Ref. 0001)
[a]D: -71deg (CHCl3)(Ref. 0002)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.70(s), 21-Me 0.94(d), 19-Me 0.96(s), COOMe 3.67(s)(Ref. 0004)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)







[0001] / [0002] / [0004] / [0007]
135
3,6-Dioxo-5a-cholan-24-oic Acid
 BBA0135
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

206-208degC, (Me ester; mp, 149-151.5degC)(Ref. 0066/0237)
[a]D: 0.0deg(Ref. 0001)
[a]d-22: +7.5deg (dioxane) (Me ester)(Ref. 0001/0237)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.70(s), 21-Me 0.94(d), 19-Me 0.96(s), COOMe 3.67(s)(Ref. 0004)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)







[0001] / [0004] / [0007] / [0066] / [0237]
136
3,7-Dioxo-5b-cholan-24-oic Acid
 BBA0136
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

145degC, (Me ester; mp, 152-155degC)(Ref. 0067)
[a]D: -36deg (C=0.2, CHCl3)(Ref. 0067)
[a]D: -27deg (CH3COCH3)(Ref. 0002)
nmax m: 9.6-9.7, 9.91(Ref. 0003)
Me ester: nmaxcm-1: 1740 (COOMe), 1715 (C=O)(Ref. 0067)
Me ester 1H-NMR (CDCl3) d: 0.70 (3H, s, 18-CH3), 1.31 (3H, s, 19-CH3), 0.92 (3H, d, J=5Hz, 21-CH3), 3.7(3H, s, COOMe)(Ref. 0005/0067)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.4, C-2 36.6, C-3 210.7, C-4 42.9, C-5 47.7, C-6 44.9, C-7 209.7, C8 49.5, C-9 42.9, C-10 35.4, C-11 22.1, C-12 38.9, C-13 42.9, C-14 48.9, C-15 24.7, C-16 28.1, C-17 54.8, C-18 12.0, C-19 22.3, C-20 35.1, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.3, C-25 51.3(Ref. 0004/0064/0140)
Me ester (70eV) m/z: 402(M+, 62%), 387(M-CH3, 4%), 384(M-H2O, 6%), 370(M-32, 28%), 353(M-H2O-31, 26%), 329(M-73, 33%), 287(M-SC, 100%), 269(M-H2O-SC, 40%), 261(M-SC-26, 5%), 260(M-SC-27, 11%), 251(M-2H2O-SC, 4%), 247(M-SC-40, 9%), 246(M-SC-41, 10%), 245(M-SC-42, 14%)(Ref. 0009)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)







[0002] / [0003] / [0004] / [0005] / [0007] / [0009] / [0064] / [0067] / [0140]
137
3,7-Dioxo-5a-cholan-24-oic Acid
 BBA0137
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

185-187degC(Ref. 0237)
162-1631degC (Me ester)(Ref. 0013/0237)
[a]d-25: -21.6pm2.0deg (C=1.0, MeOH) (Me ester)(Ref. 0013/0237)
Me ester: nmaxcm-1: 1736, 1706, 1319, 1162, 977, 906, 894(Ref. 0013)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.93(s), 21-Me 1.28(d)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.4, C-2 36.8, C-3 209.2, C-4 44.0, C-5 47.7, C-6 45.6, C-7 210.0, C-8 49.6, C-9 54.1, C-10 36.0, C-11 22.1, C-12 38.6, C-13 42.5, C-14 48.8, C-15 24.8, C-16 28.1, C-17 54.7, C-18 12.0, C-19 10.9, C-20 35.1, C-21 18.3, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.3(Ref. 0065)
Me ester (70eV) m/z: 402(M+, 56%), 384(M-H2O), 370(M-32), 353(M-18-31), 329(M-73), 287(315-SC), 269(M-H2O-SC)(Ref. 0009/0013)







[0008] / [0009] / [0013] / [0065] / [0237]
138
3,12-Dioxo-5b-cholan-24-oic Acid
 BBA0138
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

179-181deg(Ref. 0068)
133-134deg (Me ester)(Ref. 0001)
[a]d-23: +94.8deg (C=0.6, dioxane)(Ref. 0068)
[a]D: +88.5deg (C=2.2, CHCl3) (Me ester)(Ref. 0001)
nmax m: 9.6-9.7, 10.53(Ref. 0003)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.85(d), 18-Me 1.06(s), 19-Me 1.11(s)(Ref. 0004/0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.8, C-2 36.8, C-3 211.6, C-4 42.0, C-5 43.7, C-6 25.5, C-7 26.6, C-8 35.4, C-9 44.3, C-10 35.6, C-11 38.3, C-12 213.7, C-13 57.5, C-14 58.5, C-15 24.2, C-16 27.4, C-17 46.5, C-18 11.7, C-19 22.1, C-20 35.6, C-21 18.5, C-22 31.3, C-23 30.5, C-24 174.4, C-25 51.3(Ref. 0004/0064/0140)
Me ester (70eV) m/z: 402(M+, 100%), 387(M-CH3, 3%), 384(M-H2O, 8%), 370(M-32, 7%), 353(M-H2O-31, 2%), 329(M-73, 18%), 287(M-SC, 15%), 269(M-H2O-SC, 12%), 261(M-SC-26, 5%), 260(M-SC-part of ring D (27), 9%), 251(M-2H2O-SC, 7%), 247(M-SC-40, 86%), 246(M-SC-41, 2%), 245(M-SC-ring D (42), 12%)(Ref. 0009)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Detected in human feces.(Ref. 0101/0161/0205)




[0001] / [0003] / [0004] / [0005] / [0007] / [0009] / [0064] / [0068] / [0101] / [0140] / [0161] / [0205]
139
3,12-Dioxo-5a-cholan-24-oic Acid
 BBA0139
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

225degC(Ref. 0001/0237)
162-163degC (Me ester)(Ref. 0013/0237)
[a]D: +87.2deg(Ref. 0237)
[a]d-25: +88.0pm1.5deg (C=0.55, MeOH) (Me ester)(Ref. 0013/0237)
Me ester: nmaxcm-1: 3472, 1709, 1207, 1077, 952(Ref. 0013)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.86(d), 18-Me 1.05(s), 19-Me 1.10(s)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.9, C-2 37.7, C-3 210.5, C-4 44.3, C-5 46.4, C-6 28.6, C-7 30.9, C-8 35.1, C-9 56.5, C-10 36.3, C-11 38.5, C-12 213.8, C-13 57.2, C-14 58.0, C-15 24.3, C-16 27.3, C-17 46.1, C-18 11.6, C-19 11.1, C-20 35.5, C-21 18.5, C-22 31.2, C-23 30.4, C-24 174.4, C-25 51.3(Ref. 0065)
Me ester (70eV) m/z: 402(M+, 62%), 387(M-CH3, 2%), 384(M-H2O, 7%), 370(M-32, 3%), 353(M-H2O-31, 2%), 329(M-73, 15%), 287(M-SC, 20%), 269(M-H2O-SC, 9%), 261(M-SC-26, 1%), 260(M-SC-part of ring D (27), 5%), 251(M-2H2O-SC, 1%), 247(M-SC-40, 100%), 246(M-SC-41, 4%), 245(M-SC-ring D (42), 8%)(Ref. 0009)







[0001] / [0008] / [0009] / [0013] / [0065] / [0237]
140
7,12-Dioxo-5b-cholan-24-oic Acid
 BBA0140
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

180-182.5degC, (Me ester; mp, 136.5-137.5degC)(Ref. 0063)
[a]D: +26deg (dioxane)(Ref. 0002)
[a]D: +97deg (C=0.1, MeOH)(Ref. 0001)
nmaxcm-1: 1720-1710, 1700cm-1(Ref. 0063)
1H-NMR (CDCl3) d: 18-Me 1.05 (3H, s), , 19-Me 1.31 (3H, s)
Me ester 1H-NMR (CDCl3) d: 18-Me 1.04 (s), 19-Me 1.30(s), COOMe 3.68(s)(Ref. 0005/0063)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.4, C-2 20.4, C-3 26.2, C-4 28.2, C-5 46.7, C-6 45.8, C-7 209.8, C-8 49.0, C-9 45.6, C-10 36.6, C-11 38.4, C-12 212.8, C-13 56.9, C-14 52.0, C-15 25.3, C-16 27.7, C-17 45.6, C-18 11.8, C-19 23.3, C-20 35.6, C-21 18.7, C-22 31.3, C-23 30.5, C-24 174.5, C-25 51.4(Ref. 0004/0064)
m/z: 388 (M+), 370, 287, 247(100%)(Ref. 0063)
M ester m/z: 402 (M+), 287, 247(100%)(Ref. 0009/0063)







[0001] / [0002] / [0004] / [0005] / [0009] / [0063] / [0064]
141
7,12-Dioxo-5a-cholan-24-oic Acid
 BBA0141
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

194degC, (Me ester; mp, 143-144degC)(Ref. 0038/0237)
[a]d-25: +11.0pm1deg (C=0.94)(Ref. 0038/0237)
[a]d-25: +9.4deg (C=0.99, MeOH) (Me ester)(Ref. 0001/0237)
nmaxcm-1: 3226, 1736, 1706, 1698, 897, 789(Ref. 0038)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.84(d), 18-Me 1.04(s), 19-Me 1.15(s)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.3, C-3 26.0, C-4 28.7, C-5 48.3, C-6 46.2, C-7 209.2, C-8 49.3, C-9 58.0, C-10 37.1, C-11 37.9, C-12 212.7, C-13 56.4, C-14 51.6, C-15 25.1, C-16 27.4, C-17 45.3, C-18 11.5, C-19 11.1, C-20 35.3, C-21 18.4, C-22 31.0, C-23 30.3, C-24 174.1, C-25 51.1(Ref. 0065)
Me ester (70eV) m/z: 402(M+, 41%), 387(M-CH3, 4%), 384(M-H2O, 27%), 370(M-32, 5%), 366(M-2H2O, 3%), 353(M-H2O-31, 7%), 329(M-73, 11%), 287(M-SC, 28%), 269(M-H2O-SC, 17%), 261(M-SC-26, 5%), 260(M-SC-part of ring D (27), 10%), 251(M-2H2O-SC, 3%), 247(M-SC-40, 100%), 246(M-SC-41, 4%), 245(M-SC-ring D (42), 3%)(Ref. 0009)







[0001] / [0008] / [0009] / [0038] / [0065] / [0237]
142
5b-Chol-9(11)-en-24-oic Acid
 BBA0142
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

139-140.8degC, (Me ester; mp, 67.4-68.2degC)(Ref. 0055)
[a]d-21: +40.2pm2deg (2.59%, CHCl3)(Ref. 0055)
[a]d-25: +39deg (Me ester)(Ref. 0002)
Me ester: nCS2max mm: 3.22, 3.45-3.55, 5.75, 8.55(Ref. 0055)









[0002] / [0055]
143
5b-Chol-11-en-24-oic Acid
 BBA0143
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

133-135degC(Ref. 0001/0220)
58-59degC (Me ester)(Ref. 0069/0220)
[a]d-25: +29.0deg (Me ester)(Ref. 0069)
[a]d-12: +34.1pm2deg (C=1.99, acetone) (Me ester)(Ref. 0220)









[0001] / [0069] / [0220]
144
5b-Chol-14-en-24-oic Acid
 BBA0144
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

143-144degC(Ref. 0072)
[a]d-22: +61.8deg (CHCl3)(Ref. 0072)
emax (EtOH): 3404(Ref. 0072)
Me ester 1H-NMR (CDCl3) d: 18- and 19-Me 0.91(s), 15-H 5.15(Ref. 0070)
Me ester m/z: 373(M+), 257(100%)(Ref. 0070)







[0070] / [0072]
145
6a,7a-Dihydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0145
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

195-197degC(Ref. 0073)
[a]D: +12deg(Ref. 0073)
1H-NMR (DMSO-d6; 270MHz) d: 0.64 (3H, s, 18-CH3), 0.89 (3H, d, J=6.3Hz, 21-CH3), 0.94 (3H, 3H, s, 19-CH3), 3.61 (2H, m, 6b- and 7b-H)(Ref. 0073)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0007] / [0073]
146
3a-Hydroxy-6-oxo-5b-cholan-24-oic Acid
 BBA0146
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

170-173degC(Ref. 0001)
143-144degC (Me ester)(Ref. 0018)
[a]d-25: -38.6pm3deg (dioxane) (Me ester)(Ref. 0001)
Me ester: nmaxcm-1: 1725, 1695 (C=O), 3510, 1064 (OH)(Ref. 0018)
1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.76(s), 21-Me 0.95(d), 3b-H 3.58(w1/2, 30)(Ref. 0004)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.84(s), 21-Me 0.93(d), 3b-H 3.57(brm), COOMe 3.66(s)(Ref. 0018)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0001] / [0004] / [0007] / [0018]
147
3b-Hydroxy-6-oxo-5b-cholan-24-oic Acid
 BBA0147
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

188degC(Ref. 0001)
122-123degC (Me ester-3-formate)(Ref. 0018)
Me ester-3-formate: nmaxcm-1: 1722, 1702 (C=O), 1198 (ester)(Ref. 0018)
Me ester-3-formate 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.89(s), 21-Me 0.93(d), COOMe 3.66(s), 3a-H 5.25(m), -CHO 8.03(s)(Ref. 0018)








[0001] / [0018]
148
3a-Hydroxy-6-oxo-5a-cholan-24-oic Acid
 BBA0148
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

188-190degC, (Me ester; mp, 138-140degC)(Ref. 0019/0237)
185degC (Me ester-3-acetate)(Ref. 0001)
[a]D: 0.0deg(Ref. 0237)
[a]d-25: -8deg (C=1.0, CHCl3) (Me ester-3-acetat)(Ref. 0036)
nmaxcm-1: 1698, 3490, 1005(Ref. 0019)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.71(s), 21-Me 0.93(d), 3b-H 4.07(m)(Ref. 0019)Me ester 1H-NMR (CDCl3) d: 18-Me 0.68(s), 19-Me 0.74(s), 21-Me 0.94(d), COOMe 3.67(s), 3b-H 4.15(w1/2, 12)(Ref. 0004)
Me ester (70eV) m/z: 404(M+, 100%), 386(M-H2O, 21%), 372(M-32, 11%), 371(M-H2O-CH3, 18%), 368(M-2H2O, 3%), 355(M-H2O-31, 10%), 353(M-2H2O-CH3, 3%), 331(M-73, 34%), 314(M-H2O-72, 5%), 313(M-H2O-73, 17%), 289(M-SC, 11%), 271(M-H2O-SC, 1%), 262(M-SC-27, 21%), 253(M-2H2O-SC, 1%), 249(M-SC-40, 6%), 247(28%), 244(M-H2O-SC-part of ring D (27), 6%), 231(M-H2O-SC-40, 9%), 230(M-H2O-SC-41, 7%), 229(M-H2O-SC-ring D (42), 21%), 217(5%), 215(5%)(Ref. 0009)
Me ester-3-acetate (70eV) m/z: 386(M-AcOH, 100%)(Ref. 0036)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Constituent of pig and rat bile.(Ref. 0001/0101)




[0001] / [0004] / [0007] / [0009] / [0019] / [0036] / [0101] / [0237]
149
3b-Hydroxy-6-oxo-5a-cholan-24-oic Acid
 BBA0149
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

247-249degC, (Me ester; mp, 149-151degC)(Ref. 0019)
93-95degC (Me ester)(Ref. 0001/0237)
[a]D: -11deg(Ref. 0237)
nmaxcm-1: 1726, 1690 (C=O), 3435, 1022, 997 (OH)(Ref. 0019)
Me ester: nmaxcm-1: 1712 (C=O), 3477, 1024, 1003 (OH)(Ref. 0019)
1H-NMR (CDCl3; 90MHz) d: 18-Me 0.67(s), 19-Me 0.73(s), 21-Me 0.93(d), 3a-H 3.53(brm)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.75(s), 21-Me 0.93(d), 3a-H 3.51(brm), COOMe 3.66(s)(Ref. 0004/0019)








[0001] / [0004] / [0019] / [0237]
150
7-Ketolithocholic Acid
3a-Hydroxy-7-oxo-5b-cholan-24-oic Acid
 BBA0150
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

201-203degC(Ref. 0075)
107-109degC (Me ester)(Ref. 0076)
[a]d-21: -3.16pm2deg (C=0.99, CHCl3)(Ref. 0258)
[a]d-20: -38.0pm2deg (C=1.63, CHCl3) (Me ester)(Ref. 0076)
nmax m: 9.33, 9.6-9.7, 9.91, 10.25(Ref. 0003)
nmaxcm-1: 1400, 1410, 1700, 1920, 2550, 2850, 2900, 3520(Ref. 0258)
1H-NMR (CDCl3) d: 3H 0.65(s), 3H 0.65(s), 3H 0.88(d, J, 6.3), 3H 1.19(s), 23H 1.02-2.01(m), 4H 2.13-2.46(m), 1H 2.65(dd, J, 5.9, 12.0), 1H 3.60(m)(Ref. 0258)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.65(s), 21-Me 0.95(d), 19-Me 1.20(s), COOMe 3.62(s), 3a-H 3.50(brm)(Ref. 0004)
Me ester 13C-NMR (CDCl3; 67.8MHz) d: C-1 34.1, C-2 29.7, C-3 70.5, C-4 37.2, C-5 46.0, C-6 45.3, C-7 212.2, C-8 48.8, C-9 42.7, C-10 35.0, C-11 21.6, C-12 38.9, C-13 42.5, C-14 49.4, C-15 24.7, C-16 28.1, C-17 54.7, C-18 11.9, C-19 22.9, C-20 35.1, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0140)
Me ester (70eV) m/z: 404(M+, 52%), 386(M-H2O, 69%), 372(M-32, 18%), 371(M-H2O-CH3, 26%), 368(M-2H2O, 38%), 355(M-H2O-31, 23%), 353(M-2H2O-CH3, 36%), 331(M-73, 23%), 314(M-H2O-72, 25%), 313(M-H2O-73, 24%), 292(80%), 289(M-SC, 54%), 271(M-H2O-SC, 59%), 262(M-SC-part of ring D (27), 9%), 253(M-2H2O-SC, 55%), 249(M-SC-40, 25%), 247(12%), 244(M-H2O-SC-27, 13%), 231(M-H2O-SC-40, 15%), 230(M-H2O-SC-41, 11%), 229(M-H2O-SC-ring D (42), 24%), 217(17%), 215(13%), 194(49%)(Ref. 0009)
Me ester-3-acetate (70eV) m/z: 386(M-AcOH, 100%)(Ref. 0036)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Detected in human bile, serum and feces.(Ref. 0001/0101/0160/0161)
Isolated from the bile of pig, coypu, chicken, and a number of mammalian species.(Ref. 0101)
Primary bile acid in koala and guinea pig.(Ref. 0102)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)




[0001] / [0003] / [0004] / [0007] / [0009] / [0036] / [0075] / [0076] / [0101] / [0102] / [0140] / [0155] / [0160] / [0161] / [0191] / [0258]
151
3b-Hydroxy-7-oxo-5b-cholan-24-oic Acid
 BBA0151
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

247-248degC (Ref. 0001)









[0001]
152
3b-Hydroxy-7-oxo-5a-cholan-24-oic Acid
 BBA0152
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

185-197degC(Ref. 0041/0237)
147-149degC (Me ester)(Ref. 0041/0237)
[a]d-20: -41.6pm0.5deg (C=1%, MeOH)(Ref. 0041)
[a]D: -41.6deg (Me ester)(Ref. 0237)

Me ester (70eV) m/z: 404(M+, 49%), 386(M-H2O, 11%), 372(M-32, 24%), 371(M-H2O-CH3, 7%), 355(M-H2O-31, 16%), 353(M-2H2O-CH3, 7%), 331(M-73, 29%), 313(M-H2O-73, 3%), 292(12%), 289(M-SC, 15%), 271(M-H2O-SC, 35%), 262(M-SC-part of ring D (27), 13%), 253(M-2H2O-SC, 8%), 249(M-SC-40, 24%), 247(37%), 244(M-H2O-SC-27, 3%), 231(M-H2O-SC-40, 3%), 230(M-H2O-SC-41, 4%), 229(M-H2O-SC-ring D (42), 6%), 217(4%), 215(5%), 194(100%)(Ref. 0009)







[0009] / [0041] / [0237]
153
3a-Hydroxy-11-oxo-5b-cholan-24-oic Acid
 BBA0153
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

222-224degC, (Me ester; mp, 99-102degC)(Ref. 0077)
131-133.2degC (Me ester-3-acetate)(Ref. 0055)
[a]D: +62deg (C=1.02, MeOH) (Me ester)(Ref. 0001)
[a]d-25: +70deg (C=1.0%, CHCl3) (Me ester-3-acetate)(Ref. 0077)









[0001] / [0055] / [0077]
154
3b-Hydroxy-11-oxo-5b-cholan-24-oic Acid
 BBA0154
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

152-153degC(Ref. 0001)
174.8-176.2degC (Me ester-3-acetate)(Ref. 0055)
[a]d-21: +39.4deg (C=0.939, CH3COCH3) (Me ester)(Ref. 0001)
[a]d-23: +39.6pm2deg (2.22%, acetone) (Me ester-3-acetate)(Ref. 0055)









[0001] / [0055]
155
12-Ketolithocholic Acid
3a-Hydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0155
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

165degC<0001>>
112.0-113.6degC (Me ester)(Ref. 0025)
nmax m: 9.71, 10.22(Ref. 0003)
Me ester-3-acetate 13C-NMR (CDCl3; 67.8MHz) d: C-1 34.9, C-2 26.3, C-3 73.6, C-4 32.1, C-5 41.3, C-6 26.9, C-7 25.9, C-8 35.6, C-9 43.9, C-10 35.3, C-11 38.0, C-12 214.4, C-13 57.4, C-14 58.5, C-15 24.2, C-16 27.4, C-17 46.4, C-18 11.6, C-19 22.7, C-20 35.5, C-21 18.5, C-22 31.3, C-23 30.4, C-24 174.5, C-25 51.3, 170.4, 21.3(Ref. 0140)
Me ester (70eV) m/z: 404(M+, 100%), 386(M-H2O, 84%), 372(M-32, 2%), 371(M-H2O-CH3, 4%), 368(M-2H2O, 2%), 355(M-H2O-31, 1%), 353(M-2H2O-CH3, 1%), 331(M-73, 11%), 313(M-H2O-73, 8%), 289(M-SC, 14%), 271(M-H2O-SC, 3%), 262(M-SC-part of ring D (27), 2%), 253(M-2H2O-SC, 9%), 249(M-SC-40, 47%), 247(3%), 244(M-H2O-SC-27, 1%), 231(M-H2O-SC-40, 53%), 230(M-H2O-SC-41, 2%), 229(M-H2O-SC-ring D (42), 11%), 217(2%), 215(3%)(Ref. 0009)
Me-TFA (24eV) m/z: 500(M+, 100%), 386(M-114), 345(M-155), 231(M-114-155), 229(M-114-157)(Ref. 0138)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)
Me ester-3-acetate (70eV) m/z: 446(M, 100%), 386(M-AcOH, 35%), 313(15%), 291(15%), 271(25%), 253(20%), 231(100%), 229(25%)(Ref. 0231)


Isolated from human bile, serum and faeces.(Ref. 0001/0160/0161)
Identified in the bile of beef and in the feces of several species.(Ref. 0101)
Identified in urine and feces of healthy humans and patients with liver cirrhosis.(Ref. 0138/0150/0151/0212)
A major bile acid of gallbladder bile of Varanus monitor (species Varanidae).(Ref. 0142)
Faecal bile acid identified from a patient with familial adenomatous polyposis.(Ref. 0154)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Excreted in duodenal bile and urine of diabetic patients.(Ref. 0221)
Identified in feces of patients with cororectal cancer or polyps.(Ref. 0243)




[0001] / [0003] / [0007] / [0009] / [0025] / [0101] / [0138] / [0140] / [0142] / [0150] / [0151] / [0154] / [0160] / [0161] / [0191] / [0206] / [0212] / [0221] / [0231] / [0243]
156
3b-Hydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0156
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

127-129degC (Me ester)(Ref. 0078)
[a]d-20: +82deg (C=0.9, CHCl3)(Ref. 0078)
Me ester: nmaxcm-1: 1740, 1440, 1251, 1175 (COOMe), 1702, 1695, (>C=O), 3615, 1030 (OH)(Ref. 0078)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 1.02(s), 19-Me 1.05(s), COOMe 3.65(s), 3a-H 4.08(m)(Ref. 0078)



Detected in the feces of rabbits.(Ref. 0101)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Identified in human feces.(Ref. 0161)




[0078] / [0101] / [0150] / [0151] / [0161]
157
12b-Hydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0157
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

129.5-131.0degC (Me ester)(Ref. 0014)
Me ester: nmaxcm-1: 1725, 1690 (C=O), 3440, 1053, 1023, 975, 952 (OH)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.76(s), 21-Me 1.01(d), 19-Me 1.02(s), 12a-H 3.40(brm), COOMe 3.64(s)(Ref. 0014)








[0014]
158
6a-Hydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0158
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

188-190degC(Ref. 0043)
99-100degC (Me ester)(Ref. 0018)
[a]D: +17deg (C=1.0, CHCl3)(Ref. 0043)
Me ester: nmaxcm-1: 1738, 1720 (C=O), 3450, 1042 (OH)(Ref. 0018)
Me ester 1H-NMR(CDCl3 ; 90MHz) d: 18-Me 0.68(s), 21-Me 0.93(d), 19-Me 1.01(s), COOMe 3.66(s), 6b-H 4.08(brm)(Ref. 0018)
Me ester (70eV) m/z: 404(M+, 9%), 386(M-H2O, 32%), 372(M-32, 5%), 371(M-H2O-CH3, 13%), 368(M-2H2O, 6%), 355(M-H2O-31, 10%), 353(M-2H2O-CH3, 7%), 331(M-73, 3%), 314(M-H2O-72, 5%), 313(M-H2O-73, 13%), 289(M-SC, 3%), 271(M-H2O-SC, 100%), 262(M-SC-part of ring D (42), 7%), 253(M-2H2O-SC, 4%), 249(M-SC-40, 9%), 247(2%), 244(M-H2O-SC-27, 14%), 231(M-H2O-SC-40, 9%), 230(M-H2O-SC-41, 8%), 229(M-H2O-SC-ring D (42), 31%), 217(6%), 215(10%)(Ref. 0009)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


A metabolite of lithocholic acid in human fetal liver.(Ref. 0164)




[0007] / [0009] / [0018] / [0043] / [0164]
159
6b-Hydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0159
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

196.5-198degC(Ref. 0074)
124-125degC (Me ester)(Ref. 0018)
[a]d-26: +15.7pm3deg (MeOH)(Ref. 0074)
Me ester: nmaxcm-1: 1740, 1710 (C=O), 3400 (OH)(Ref. 0018)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 21-Me 0.93(d), 19-Me 1.22(s), COOMe 3.67(s), 6a-H 3.72(m)(Ref. 0018)








[0018] / [0074]
160
6a-Hydroxy-3-oxo-5a-cholan-24-oic Acid
 BBA0160
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

195-197degC, (Me ester; mp, 90-97degC)(Ref. 0079/0237)
[a]d-32: +4pm2deg (C=1.059, pyridine), [a]d-27: +55pm2deg (C=1.038) (Me ester)(Ref. 0079/0237)









[0079] / [0237]
161
7a-Hydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0161
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

88-90degC(Ref. 0073)
122-124degC (Me ester)(Ref. 0040)
[a]D: +17deg (C=0.8, CHCl3)(Ref. 0067)
Me ester: nmaxcm-1: 1740 (ester C=O), 1715 (C=O), 3620-3300 (OH)(Ref. 0067)
Me ester-7-acetate: nmax m: 9.58, 9.82, 10.31, 10.65(Ref. 0003)
1H-NMR (DMSO-d6; 270MHz) d: 18-Me 0.64(s), 21-Me 0.89(d), 19-Me 0.94(s), 7b-H 3.69(q, J=3.0)(Ref. 0073)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.71(s), 21-Me 0.92(d), 19-Me 1.00(s), COOMe 3.7(s), 7b-H 3.9(m)(Ref. 0067)
Me ester (70eV) m/z: 404(M+, 9%), 386(M-H2O, 50%), 372(M-32, 7%), 371(M-H2O-CH3, 22%), 368(M-2H2O, 7%), 355(M-H2O-31, 10%), 353(M-2H2O-CH3, 23%), 314(M-H2O-72, 6%), 313(M-H2O-73, 7%), 271(M-H2O-SC, 100%), 262(M-SC-part of ring D (27), 17%), 253(M-2H2O-SC, 8%), 249(M-SC-40, 4%), 247(7%), 244(M-H2O-SC-27, 17%), 231(M-H2O-SC-40, 7%), 230(M-H2O-SC-41, 8%), 229(M-H2O-SC-ring D (42), 26%), 217(8%), 215(8%)(Ref. 0009)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from kangaroos and an opossum.(Ref. 0100)
Detected in human feces and serum.(Ref. 0101/0160/0161)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
A biotransformation product of chenodeoxycholic acid by Pseudomonas species NCIB 10590.(Ref. 0195)




[0003] / [0007] / [0009] / [0040] / [0067] / [0073] / [0100] / [0101] / [0155] / [0160] / [0161] / [0191] / [0195]
162
7b-Hydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0162
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

73-75degC(Ref. 0073)
103-104degC (Me ester)(Ref. 0080)
[a]D: +67deg(Ref. 0073)
1H-NMR (DMSO-d6) d: 0.65 (3H, s, 18-CH3), 0.89 (3H, d, J=6.3Hz, 21-CH3), 0.96 (3H, s, 19-CH3), 3.28 (1H, dt, J1=10.6Hz, J2=4.5Hz, 7a-H)(Ref. 0073)Me ester-7-acetate 1H-NMR (CDCl3) d: 18-Me 0.75(s), 21-Me 0.93(d), 19-Me 1.08(s), COOMe 3.62(s), 7a-H 4.73(brm)(Ref. 0004)








[0004] / [0073] / [0080]
163
7a-Hydroxy-3-oxo-5a-cholan-24-oic Acid
 BBA0163
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

143-144degC (Me ester)(Ref. 0041/0237)
[a]d-25: +18.5pm0.5deg (C=1%, MeOH)(Ref. 0041)
[a]D: +16deg (Me ester)(Ref. 0237)
Me ester: nmaxcm-1: 3472 (OH), 1736 (COOMe), 1701 (C=O), 1172(COOMe), 1076 (OH), 1040 (OH)(Ref. 0041)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 21-M 0.93(d), 19-Me 1.01(s), COOMe 3.66(s), 7b-H 3.86(m)(Ref. 0024)
Me ester (70eV) m/z: 404(M+, 12%), 386(M-H2O, 87%), 372(M-32, 11%), 371(M-H2O-CH3, 29%), 368(M-2H2O, 8%), 355(M-H2O-31, 22%), 353(M-2H2O-CH3, 19%), 331(M-73, 5%), 314(M-H2O-72, 5%), 313(M-H2O-73, 10%), 271(M-H2O-SC, 94%), 262(M-SC-part of ring D (27), 42%), 253(M-2H2O-SC, 4%), 249(M-SC-40, 6%), 247(35%), 244(M-H2O-SC-27, 43%), 231(M-H2O-SC-40, 20%), 230(M-H2O-SC-41, 15%), 229(M-H2O-SC-ring D (42), 46%), 217(14%), 215(15%)(Ref. 0009)Me-TMS ether (20eV) m/z: 476(M+), 386(M-TMSOH), 271(M-2TMSOH-SC), 316(Ref. 0041)







[0009] / [0024] / [0041] / [0237]
164
7a-Hydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0164
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

98-100degC, (Me ester; mp, 113.5-114.5degC)(Ref. 0026)
nmaxcm-1: 1678, 1706 (C=O), 3390, 1032, 1017, 1000, 985, 909 (OH)(Ref. 0026)
1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 1.00(s), 19-Me 1.02(s), 7b-H 3.84(m)(Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.99(s), 19-Me 1.01(s), COOMe 3.63(s), 7b-H 3.92(m)(Ref. 0026)








[0026]
165
7b-Hydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0165
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

185.5-187.5degC, (Me ester; mp, 114-115degC)(Ref. 0026)
Me ester: nmaxcm-1: 1706 (C=O), 3333, 1018 (OH)(Ref. 0026)
1H-NMR (CDCl3; 100MHz) d: 18- and 19-Me 1.04(s), 7a-H 3.59(brm), (Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18- and 19-Me 1.04(s), 7a-H 3.56(brm), COOMe 3.63(s)(Ref. 0026)








[0026]
166
7a-Hydroxy-12-oxo-5a-cholan-24-oic Acid
 BBA0166
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

185-186.5degC, (Me ester; mp, 122-123degC)(Ref. 0028/0237)
[a]D: +53.8deg(Ref. 0237)
[a]d-25: +41.2deg (C=0.29, MeOH) (Me ester)(Ref. 0001/0237)
nmaxcm-1: 1710, 1692, (C=O), 3400, 1022 (OH)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.85, 18-Me 0.87(s), 19-Me 1.02(s), COOMe 3.63(s), 7b-H 3.90(m)(Ref. 0028)








[0001] / [0028] / [0237]
167
7b-Hydroxy-12-oxo-5a-cholan-24-oic Acid
 BBA0167
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

219-220degC, (Me ester; mp, 107-108degC)(Ref. 0028)
nmaxcm-1: 1710, 1682 (C=O), 3300, 1030, 990 (OH)(Ref. 0028)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 21-Me 0.83(d), 18-Me 0.89(s), 19-Me 1.04(s), 7a-H 3.55(brm)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.86(d), 18-Me 0.90(s), 19-Me 1.05(s), 7a-H 3.34(brm), COOMe 3.66(s)(Ref. 0028)








[0028]
168
12a-Hydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0168
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

103-105degC(Ref. 0073)
156-158degC(Ref. 0001)
148-149degC (Me ester)(Ref. 0080/0259)
[a]D: +52deg (C=1.0, EtOH)(Ref. 0001)
Me ester: nmaxcm-1: 1720 (C=O), 3521(0H)(Ref. 0081/0259)
Me ester-12-acetate: nmax m: 9.58, 9.75, 10.32(Ref. 0003)
1H-NMR (DMSO-d6; 270MHz) d: 18-Me 0.63(s), 21-M 0.92(d), 19-Me 0.94(s), 12b-H 3.82(t, J=2.8)(Ref. 0073)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.73(s), 21-M 1.00(d), 19-Me 1.02(s), COOMe 3.67(s), 12b-H 4.04(m)(Ref. 0004/0259)
Me ester (70eV) m/z: 404(M+, 10%), 386(M-H2O, 13%), 372(M-32, 1%), 371(M-H2O-CH3, 3%), 368(M-2H2O, 1%), 355(M-H2O-31, 4%), 353(M-2H2O-CH3, 2%), 331(M-73, 1%), 314(M-H2O-72, 2%), 313(M-H2O-73, 5%), 289(M-SC, 1%), 271(M-H2O-SC, 100%), 262(M-SC-part of ring D (27), 1%), 253(M-2H2O-SC, 10%), 249(M-SC-40, 1%), 247(8%), 244(M-H2O-SC-27, 4%), 231(M-H2O-SC-40, 4%), 230(M-H2O-SC-41, 2%), 229(M-H2O-SC-ring D (42), 1%), 217(3%), 215(4%)(Ref. 0009/0259)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Detected in human feces and serum.(Ref. 0101/0160/0161/0205)




[0001] / [0003] / [0004] / [0007] / [0009] / [0073] / [0080] / [0081] / [0101] / [0160] / [0161] / [0205] / [0259]
169
12a-Hydroxy-3-oxo-5a-cholan-24-oic Acid
 BBA0169
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

141.5-143degC (Me ester)(Ref. 0014/0237)
[a]d-25: +51.7pm0.5deg (C=1.0, MeOH)(Ref. 0013)
[a]D: +51.7deg (Me ester)(Ref. 0237)
Me ester: nmaxcm-1: 1725, 1708 (C=O), 3470, 1030, 1017, 967, 955 (OH)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 19-Me 1.01(s), COOMe 3.65(s), 12b-H 3.97(m)(Ref. 0014)
Me ester (70eV) m/z: 404(M+, 2%), 386(M-H2O, 5%), 372(M-32, 1%), 371(M-H2O-CH3, 3%), 368(M-2H2O, 1%), 355(M-H2O-31, 4%), 331(M-73, 1%), 314(M-H2O-72, 1%), 313(M-H2O-73, 2%), 289(M-SC, 1%), 271(M-H2O-SC, 100%), 262(M-SC-part of ring D (27), 1%), 253(M-2H2O-SC, 3%), 249(M-SC-40, 1%), 247(8%), 244(M-H2O-SC-27, 4%), 231(M-H2O-SC-40, 4%), 230(M-H2O-SC-41, 5%), 229(M-H2O-SC-ring D (42), 6%), 217(4%), 215(3%)(Ref. 0009)







[0009] / [0013] / [0014] / [0237]
170
5b-Chol-2-en-24-oic Acid
 BBA0170
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

Me ester 1H-NMR (CDCl3; 60MHz) d: 5.50(m)(Ref. 0105)
Me ester m/z: 372(M+, 100%), 357(M-CH3, 49%), 318(M-54, 51%), 257(M-SC, 39%), 203(M-SC-54, 35%), 215(79%)(Ref. 0105)







[0105]
171
12a-Hydroxy-7-oxo-5a-cholan-24-oic Acid
 BBA0171
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

192-193degC, (Me ester; mp, 164-165degC)(Ref. 0038/0237)
[a]d-25: -19.1pm1deg (C=0.83, MeOH), [a]d-25: -13.8pm0.5deg (C=1.01, MeOH) (Me ester)(Ref. 0038/0237)
nmaxcm-1: 3484, 3322, 1706, 1304, 1280, 1078, 1043, 1025, 959, 917, 853(Ref. 0038)









[0038] / [0237]
172
2b,3b-Dihydroxy-6-oxo-5a-cholan-24-oic Acid
 BBA0172
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

235degC, (Me ester-2,3-diacetate; mp, 170-172degC)(Ref. 0082)









[0082]
173
3a,6a-Dihydroxy-7-oxo-5b-cholan-24-oic Acid
 BBA0173
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

184 - 186degC(Ref. 0029)
[a]d-25: -47.5pm1deg (C=0.393, MeOH)(Ref. 0083)
nmaxcm-1: 1718 (C=O), 3400, 1055, 1018(Ref. 0029)
1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 21-Me 0.94(d), 19-Me 1.23(s), 3b-H 3.55(brm), 6b-H 4.52(d, J, 6.3)(Ref. 0029)








[0029] / [0083]
174
3a,7a-Dihydroxy-6-oxo-5b-cholan-24-oic Acid
 BBA0174
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

234-236degC(Ref. 0001)
149-150degC (Me ester-3,7-diacetate)(Ref. 0084)
[a]13D: -7.4deg (C=0.5, CHCl3)(Ref. 0084)
[a]d-30: +62.3deg (C=0.62, CHCl3) (Me ester-3,7-diacetate)(Ref. 0084)
Me ester: nmaxcm-1: 3400, 1735, 1705(Ref. 0084)
Me ester-3,7-diacetate: nmaxcm-1: 1205, 1707, 1742(Ref. 0084)
Me ester 1H-NMR(CDCl3) d: 18-Me 0.66(s), 19-Me 0.83(s), 21-Me 0.93(d), COOMe 3.66(s), 3b-H 3.75(br), 7b-H 3.95(d, J, 5.0)(Ref. 0084)
Me ester-3,7-diacetate 1H-NMR(CDCl3) d: 18-Me 0.66(s), 19-Me 0.86(s), 21-Me 0.94(d), 3a-OCOMe 2.04(s), COOMe 3.67(s), 3b-H 4.58(br), 7b-H 4.89(d, J, 3.5)(Ref. 0084)
Me ester-3,7-diacetate m/z: 505(M++1)(Ref. 0084)







[0001] / [0084]
175
3a,7b-Dihydroxy-6-oxo-5a-cholan-24-oic Acid
 BBA0175
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

223-224degC<0037/0237)
136-139degC (Me ester)(Ref. 0037)
[a]d-25: +39.6pm1deg (C=0.19, MeOH)(Ref. 0083/0237)
nmaxcm-1: 1719, 1686 (C=O), 3540, 1007 (OH)(Ref. 0037)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18- and 19-Me 0.67(s), 21-Me 0.94(s), 7a-H 3.71(d, J,9.0), 3b-H 4.00(m)(Ref. 0037)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18- and 19-Me 0.68(s), COOMe 3.66(s), 7a-H 3.77(d, J,9.0), 3b-H 4.13(m)(Ref. 0037)








[0037] / [0083] / [0237]
176
12-Kotochenodeoxycholic Acid
3a,7a-Dihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0176
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

222-224degC(Ref. 0001)
154.5-161.5degC (Me ester)(Ref. 0032)
[a]D: +78deg (MeOH)(Ref. 0086)
nmax m: 9.32, 9.6-9.7, 9.86, 10.33(Ref. 0003)
Me ester-3,7-diacetate: nmax m: 9.41, 9.78, 10.32, 1065(Ref. 0003)
1H-NMR (DMSO-d6; 270MHz) d: 21-Me 0.76(d), 18-Me 0.96(s), 19-Me 0.94(s), 3b-H 3.18(sept, J, 10.7, 4.6), 7b-H 3.71(q, J, 3.0)(Ref. 0086)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18- and 19-Me 1.03(s), 3b-H 3.50(brm), COOMe 3.70(s), 7b-H 3.93(m)(Ref. 0032)
Me ester-3,7-diacetate 1H-NMR(CDCl3) d: 21-Me 1.00(d), 18- and 19-Me 1.05(s), 3a- and 7a-OCOMe 2.01(s), 23-H2 2.30(m), COOMe 3.60(s), 3b-H 4.50(brm), 7b-H 4.92(m)(Ref. 0247)
Me ester 13C-NMR (CDCl3) d: C-1 35.4, C-2 30.3, C-3 71.4, C-4 39.5, C-5 41.1, C-6 34.9, C-7 67.7, C-8 39.3, C-9 37.1, C-10 35.8, C-11 37.7, C-12 215.1, C-13 57.0, C-14 53.4, C-15 23.7, C-16 27.5, C-17 46.3, C-18 11.5, C-19 22.2, C-20 35.6, C-21 18.6, C-22 31.2, C-23 30.5, C-24 174.7(Ref. 0137)
Me-TFA (24eV) m/z: 612(M+), 498(M-114), 457(M-155), 343(M-144-155), 229(M-2times114-155, 100%)(Ref. 0138)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)
Me ester-3,7-diacetate (70eV) m/z: 504(M, 4%), 444(M-AcOH, 56%), 384(M-2AcOH, 22%), 369(7%), 366(7%), 353(11%), 311(18%), 289(18%), 269(24%), 251(24%), 243(36%), 229(100%)(Ref. 0231)


An oxidoreduction product of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases.(Ref. 0086)
Detected in human feces and serum.(Ref. 0101/0160)
Identified in urine and feces of a patients with liver cirrhosis.(Ref. 0138)
Identified in human feces.(Ref. 0162)
Isolated from biliary bile in cholecystectomized patients.(Ref. 0170)
Isolated from the bile of patients with hepatobiliary diseases.(Ref. 0179/0191)
Identified in urine of infants during the neonatal period.(Ref. 0211)




[0001] / [0003] / [0007] / [0032] / [0086] / [0101] / [0137] / [0138] / [0160] / [0162] / [0170] / [0179] / [0191] / [0211] / [0231] / [0247]
177
3a,7b-Dihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0177
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

138.0-139.5degC(Ref. 0031)
nmaxcm-1: 1740, 1670 (C=O)(Ref. 0031)
1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18- and 19-Me 1.08(s), 3b- and 7a-H 3.58(brm)(Ref. 0031)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18- and 19-Me 1.04(s), 3b- and 7a-H 3.56(brm), COOMe 3.64(s)(Ref. 0031)








[0031]
178
3b,7a-Dihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0178
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

205.0-206.0degC, (Me ester; mp, 170.0-170.5degC)(Ref. 0032)
[a]D: +93.2pm1deg (CS2) (Me ester)(Ref. 0032)
nmaxcm-1: 1695 (C=O), 1715 (COOH)(Ref. 0032)
1H-NMR (CD3COCD3+DMSO-d6; 100MHz) d: 18- and 19-Me 1.07(s), 7b-H 3.50(brm), 3a-H 3.91(m)(Ref. 0032)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18- and 19-Me 1.03(s), COOMe 3.64(s), 7b-H 3.95(m), 3a-H 4.05(m)(Ref. 0032)








[0032]
179
3b,7b-Dihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0179
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

258.0-259.0degC, (Me ester; mp, 177.0-178.0degC)(Ref. 0031)
nmaxcm-1: 1730 (ester C=O), 1672 (COOH), 3636, 3300, 1032, 986, 969, 959 (OH)(Ref. 0031)
1H-NMR (CDCl3+DMSO-d6+D2O; 100MHz) d: 18- and 19-Me 1.05(s), 7a-H 3.49(brm), 3a-H 4.00(m)(Ref. 0031)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 1.04(s), 19-Me 1.07(s), 7a-H 3.58(m), COOMe 3.64(s), 3a-H 4.04(m)(Ref. 0031)








[0031]
180
3a,7a-Dihydroxy-12-oxo-5a-cholan-24-oic Acid
 BBA0180
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

248-250degC(Ref. 0033)
nmaxcm-1: 1700, 1685 (C=O), 3400, 998 (OH)(Ref. 0033)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.86(s), 19-Me 1.02(s), 7b-H 3.83(m), 3b-H 4.07(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.84(d), 18-Me 0.87(s), 19-Me 1.02(s), COOMe 3.66(S), 7b-H 3.92(m), 3b-H 4.07(m)(Ref. 0033)








[0033]
181
3a,7b-Dihydroxy-12-oxo-5a-cholan-24-oic Acid
 BBA0181
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

264-266degC(Ref. 0033/0237)
[a]d-23: +94pm1deg (C=0.70, EtOH)(Ref. 0085/0237)
nmaxcm-1: 1732, 1695 (C=O), 3400, 1028, 1003 (OH)(Ref. 0033)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 21-Me 0.84(d), 18-Me 0.88(s), 19-Me 1.05(s), 7a-H 3.25(m), 3b-H 3.96(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.85(d), 18-Me 0.89(s), 19-Me 1.06(s), 7a-H 3.37(m), COOMe 3.66(S), 3b-H 4.07(m)(Ref. 0033)








[0033] / [0085] / [0237]
182
3b,7a-Dihydroxy-12-oxo-5a-cholan-24-oic Acid
 BBA0182
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

272-273degC, (Me ester; mp, 189-190degC)(Ref. 0033)
nmaxcm-1: 1695 (C=O), 3450, 1032 (OH)(Ref. 0033)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 21-Me 0.84(d), 18-Me 0.88(s), 19-Me 1.01(s), 3a-H 3.49(brm), 7b-H 3.81(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.87(d), 18-Me 0.90(s), 19-Me 1.03(s), 3a-H 3.58(brm), COOMe 3.66(S), 7b-H 3.93(m)(Ref. 0033)








[0033]
183
3b,7b-Dihydroxy-12-oxo-5a-cholan-24-oic Acid
 BBA0183
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

249-251degC, (Me ester; mp, 198.5-200.5degC)(Ref. 0033)
nmaxcm-1 : 1690 (C=O), 3530, 3160, 1040, 980 (OH)(Ref. 0033)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 21-Me 0.84(d), 18-Me 0.92(s), 19-Me 1.05(s), 3a- and 7a-H 3.41(brm)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.84(d), 18-Me 0.93(s), 19-Me 1.05(s), 3a- and 7a-H 3.40(brm)(Ref. 0033)








[0033]
184
7-Kotodeoxycholic Acid
3a,12a-Dihydroxy-7-oxo-5b-cholan-24-oic Acid
 BBA0184
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

194-195degC(Ref. 0086)
154-155degC (Me este)(Ref. 0034)
[a]d-25: +0.3pm1deg (C=0.99, MeOH) (Me ester)(Ref. 0013)
[a]D: -6deg (MeOH)(Ref. 0086)
Me ester : nmaxcm-1: 1737, 1695 (C=O), 3462, 1014, (OH)(Ref. 0034)
1H-NMR (DMSO-d6; 270MHz) d: 18-Me 0.59(s), 19-Me 1.11(s), 21-Me 0.92(d), 3b-H 3.34(sept, J, 10.7, 4.6), 12b-H 3.80(t, J, 2.8)(Ref. 0086)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 21-Me 0.98(d), 19-Me 1.18(s), 3b-H 3.56(brm), COOMe 3.66(s), 12b-H 3.99(m)(Ref. 0034)
Me ester 13C-NMR (CDCl3) d: C-1 34.1, C-2 29.6, C-3 70.7, C-4 37.3, C-5 46.1, C-6 45.4, C-7 212.1, C-8 49.6, C-9 35.8, C-10 34.7, C-11 29.2, C-12 72.0, C-13 46.5, C-14 40.5, C-15 24.3, C-16 27.7, C-17 46.3, C-18 12.8, C-19 22.8, C-20 35.1, C-21 17.3, C-22 31.1, C-23 30.9, C-24 174.7(Ref. 0137)
Me-TFA (24eV) m/z: 498(M-114), 384(M-2times114), 384(M-114-115, 100%), 269(M-2times114-115), 251(M-2times114-H2O-115)(Ref. 0138)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


An oxidoreduction product of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases.(Ref. 0086)
Identified in the hedgehog, Solenodon paradoxus.(Ref. 0100)
Identified in the bile of cattle, python, monkey, and rat and in the feces of human, dog, and rat.(Ref. 0101)
Identified in urine and feces of a patients with liver cirrhosis.(Ref. 0138)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in human serum or feces.(Ref. 0160/0162)
Isolated from biliary bile in cholecystectomized patients.(Ref. 0170)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Identified in urine of infants during the neonatal period.(Ref. 0211)




[0007] / [0013] / [0034] / [0086] / [0100] / [0101] / [0137] / [0138] / [0155] / [0160] / [0162] / [0170] / [0191] / [0211]
185
3b,12a-Dihydroxy-7-oxo-5b-cholan-24-oic Acid
 BBA0185
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

217.5-219.0degC, (Me ester; mp, 165.5-167.0degC)(Ref. 0031)
1H-NMR (CDCl3; 100MHz) d: 18-Me 0.69(s), 19-Me 1.21(s), 3a- and 12b-H 4.01(m)(Ref. 0031)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.69(s), 19-Me 1.22(s), COOMe 3.66(s), 3a- and 12b-H 4.02(m)(Ref. 0031)








[0031]
186
3a,12a-Dihydroxy-7-oxo-5a-cholan-24-oic Acid
 BBA0186
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

179-180degC (Me este)(Ref. 0038/0237)
[a]d-25: -11.6pm1.5deg (C=0.76, MeOH) (Me este)(Ref. 0038/0237)
nmaxcm-1: 3425, 3322, 1715, 1689, 1168, 1024, 1010, 899(Ref. 0038)









[0038] / [0237]
187
3b,12a-Dihydroxy-7-oxo-5a-cholan-24-oic Acid
 BBA0187
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

188-189degC (Me este)(Ref. 0038/0237)
[a]d-25: -5.1pm2deg (C=0.3, MeOH) (Me ester)(Ref. 0038/0237)
nmaxcm-1: 3425, 3344, 1718, 1709, 1300, 1271, 1244, 1195, 1174, 1081, 1031, 1003, 961, 948, 904, 857, 775(Ref. 0038)









[0038] / [0237]
188
3a,12b-Dihydroxy-11-oxo-5b-cholan-24-oic Acid
 BBA0188
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

202-203.5degC, (Me ester; mp, 155.5-156degC)(Ref. 0087)
[a]d-24: +65.7deg (EtOH)(Ref. 0087)
lmax (EtOH) (loge): 285 (1.67) nm(Ref. 0087)
nmaxcm-1: 3450, 1730, 1705, 1250(Ref. 0088)









[0087] / [0088]
189
3a,12a-Dihydroxy-15-oxo-5b,14b-cholan-24-oic Acid
 BBA0189
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

269-270degC, (Me ester; mp, 247-248degC)(Ref. 0058)
nmaxcm-1: 1735, 1660(Ref. 0058)
Me ester: nmaxcm-1: 3450-3350, 1740, 1735(Ref. 0058)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.99(s), 19-Me 0.99(s), COOMe 3.65(s)(Ref. 0058)
m/z: 406(M+), 388(M-H2O), 370(M-2H2O), 269(100%), 213(Ref. 0058)
Me ester m/z: 420(M+), 402(M-H2O), 384(M-2H2O), 269(M-2H2O-SC, 100%), 213(Ref. 0058)







[0058]
190
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0190
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

218-220degC(Ref. 0001)
181-183degC (Me ester)(Ref. 0080/0252)
[a]D: +41deg (MeOH)(Ref. 0086)
nmaxcm-1: 1708 (C=O)(Ref. 0081)
Me ester-7,12-diacetate: nmax m: 9.41, 9.78, 10.32, 1065(Ref. 0003)
Me ester: nmaxcm-1: 1700(3-ketone), 1720-1730(carboxy), 3450(hydroxy), 3500(hydroxy)(Ref. 0252)
1H-NMR (DMSO-d6; 270MHz) d: 18-Me 0.62(s), 21-Me 0.92(d), 19-Me 0.93(s), 7b-H 3.68(q, J, 3.0), 12b-H 3.82(t, J, 2.8)(Ref. 0086)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.67(s), 19-Me 0.96(s), 21-Me 1.21(d), COOMe 3.66(s), 12b-H 4.00(t), 7b-H 4.05(brs)(Ref. 0004/0252)
Me ester-7,12-diacetate 13C-NMR (CDCl3) d: C-1 36.4, C-2 36.9, C-3 212.9, C-4 44.8, C-5 43.5, C-6 43.5, C-7 70.9, C-8 38.0, C-9 30.0, C-10 34.6, C-11 26.0, C-12 75.6, C-13 45.3, C-14 42.4, C-15 23.0, C-16 27.3, C-17 47.6, C-18 12.4, C-19 21.5, C-20 34.8, C21 17.37, C-22 31.1, C-23 30.9, C-24 175.1(Ref. 0137)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)
Me ester-7,12-diacetate (70eV) m/z: 502(M, 2%), 443(M-AcOH, 3%), 384(M-2AcOH, 45%), 369(9%), 353(7%), 314(11%), 311(7%), 279(9%), 269(100%), 229(10%)(Ref. 0231)
Me ester m/z: 420(M+, 13%), 402(M-H2O, 42%), 384(M-2H2O, 20%), 287(M-SC-H2O, 13%), 269(M-SC-2H2O, 93%)(Ref. 0252)


An oxidoreduction product of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases.(Ref. 0086)
Isolated from cattle bile.(Ref. 0101)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in human serum.(Ref. 0160)
Identified in urine of infants during the neonatal period.(Ref. 0211)
A bacterial degradation product of cholic acid by Pseudomonas sp. N.C.I.B. 10590.(Ref. 0252)




[0001] / [0003] / [0004] / [0007] / [0080] / [0081] / [0086] / [0101] / [0137] / [0155] / [0160] / [0211] / [0231] / [0252]
191
7a,12a-Dihydroxy-3-oxo-5a-cholan-24-oic Acid
 BBA0191
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

156-157degC (Me ester)(Ref. 0038/0237)
[a]d-25: +37.0pm0.5deg (C=1.0, MeOH) (Me ester)(Ref. 0038/0237)
Me ester: nmaxcm-1: 1716 (C=O), 3400, 1035 (OH)(Ref. 0024)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.99(s), COOMe 3.66(s), 7b-H 3.86(m), 12b-H 3.98(m)(Ref. 0024)
Me-TMS ether (70eV) m/z: 564(M+), 549(M-CH3), 474(M-TMSOH), 384(M-2TMSOH), 369(M-2TMSOH-CH3), 269(M-2TMSOH-SC)(Ref. 0038)







[0024] / [0038] / [0237]
192
3a-Hydroxy-7,12-dioxo-5b-cholan-24-oic Acid
 BBA0192
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

190-191degC(Ref. 0086)
159.5-161degC (Me ester)(Ref. 0001)
[a]D: +32deg(Ref. 0086)
1H-NMR (DMSO-d6; 270MHz) d: 0.98 (3H, s, 18-CH3), 1.24 (3H, s, 19-CH3), 0.74 (3H, d, J=6.3Hz, 21-CH3), 3.33 (1H, sept, J=10.7 and 4.6Hz, 3b-H)(Ref. 0086)
Me ester 13C-NMR (CDCl3) d: C-1 34.1, C-2 29.6, C-3 70.2, C-4 37.3, C-5 45.2, C-6 45.4, C-7 209.8, C-8 48.9, C-9 45.5, C-10 35.8, C-11 38.3, C-12 212.8, C-13 56.7, C-14 51.9, C-15 25.2, C-16 27.6, C-17 45.5, C-18 11.8, C-19 22.4, C-20 35.5, C-21 18.6, C-22 31.3, C-23 30.5, C-24 174.6(Ref. 0137/0140)
Me-TFA m/z: 245(M-114-155, 100%), 359(M-155), 496(M-18), 400 (M-114), 514(M+)(Ref. 0138)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


An oxidoreduction product of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases.(Ref. 0086)
Identified in urine and feces of a patients with liver cirrhosis.(Ref. 0138)




[0001] / [0007] / [0086] / [0137] / [0138] / [0140]
193
3b-Hydroxy-7,12-dioxo-5b-cholan-24-oic Acid
 BBA0193
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

270-272degC(Ref. 0086)
151-153degC (Me ester)(Ref. 0031)
[a]D: +22deg(Ref. 0086)
1H-NMR (DMSO-d6; 270MHz) d: 0.98 (3H, s, 18-CH3), 1.26 (3H, s, 19-CH3), 0.74 (3H, d, J=6.3Hz, 21-CH3), 3.79 (1H, t, J=3.0Hz, 3a-H)(Ref. 0086)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 1.03(s), 19-Me 1.33(s), COOMe 3.65(s), 3a-H 4.07(m)(Ref. 0031)



An oxidoreduction product of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases.(Ref. 0086)




[0031] / [0086]
194
7a-Hydroxy-3,12-dioxo-5b-cholan-24-oic Acid
 BBA0194
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

193-195degC(Ref. 0086>
160-162degC (Me ester-7-acetate)(Ref. 0001)
[a]D: +73deg(Ref. 0086)
[a]10D: +64deg (Me ester-7-acetate)(Ref. 0001)
1H-NMR (DMSO-d; 270MHz) d: 1.00 (3H, s, 18-CH3), 1.05 (3H, s, 19-CH3), 0.77 (3H, d, J=6.3Hz, 21-CH3), 3.78(1H, q, J=3.3Hz, 7b-H)(Ref. 0086)
Me ester-7-acetate: Me-Ac 13C-NMR (CDCl3) d: C-1 36.3, C-2 36.5, C-3 211.1, C-4 44.4, C-5 41.9, C-6 31.1, C-7 70.3, C-8 38.6, C-9 37.8, C-10 35.7, C-11 37.8, C-12 213.3, C-13 57.1, C-14 53.0, C-15 23.7, C-16 27.3, C-17 46.3, C-18 11.5, C-19 21.3, C-20 35.5, C-21 18.5, C-22 31.0, C-23 30.4, C-24 174.5(Ref. 0137)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


An oxidoreduction product of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases.(Ref. 0086)




[0001] / [0007] / [0086] / [0137]
195
7b-Hydroxy-3,12-dioxo-5b-cholan-24-oic Acid
 BBA0195
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

187-189degC(Ref. 0086)
[a]D: +90deg (MeOH)(Ref. 0086)
1H-NMR(DMSO-d6; 270MHz) d: 1.01 (3H, s, 18-CH3), 1.05 (3H, s, 19-CH3), 0.77 (3H, d, J=6.3Hz, 21-CH3), 3.40(1H, dt, J=10.6 and 4,5Hz, 7a-H)(Ref. 0086)
MS (Positive FAB) m/z: 405((M+H)+, 100%), 387 (98%), 369 (30%), 353 (14%), 351 (17%), 341 (21%), 323 (12%), 263 (12%), 219(9%), 145(18%), 121(23%), 105 (35%)(Ref. 0086)


An oxidoreduction product of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases.(Ref. 0086)




[0086]
196
12a-Hydroxy-3,7-dioxo-5b-cholan-24-oic Acid
 BBA0196
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

168-170degC(Ref. 0086)
190*192degC (Me ester)(Ref. 0001/0259)
[a]D: -9deg(Ref. 0086)
[a]d-15: -25deg (Me ester)(Ref. 0001)
Me ester: nmaxcm-1: 1703, 1735 (C=O)(Ref. 0259)
1H-NMR(DMSO-d6; 270MHz) d: 0.63 (3H, s, 18-CH3), 1.22 (3H, s, 19-CH3), 0.93 (3H, d, J=6.3Hz, 21-CH3), 3.83 (1H, t, J=3.2Hz, 12b-H)(Ref. 0086)
Me ester 1H-NMR (CDCl3; 270MHz) d: 18-Me 0.72(s), 21-Me 0.84(d), 19-Me 1.28(s), COOMe 3.66(s), 12b-H 4.05(m)(Ref. 0259)
Me ester (70eV) m/z: 418(M+, 2%), 400(M+-H2O, 13%), 286(100%), 285(M+-H2O-SC, 89%)(Ref. 0259)


An oxidoreduction product of cholic acid and dehydrocholic acid catalyzed by hydroxysteroid dehydrogenases.(Ref. 0086)




[0001] / [0086] / [0259]
197
12a-Hydroxy-3,7-dioxo-5a-cholan-24-oic Acid
 BBA0197
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

222-223degC, (Me ester; mp, 178degC(Ref. 0013/0237)
[a]d-25: 0pm0.5deg (C=1.0, MeOH) (Me ester)(Ref. 0013/0237)
nmax cm-1: 3472, 1709, 1207, 1077, 952(Ref. 0013)

Me ester (70eV) m/z: 418(M+, 4.9%), 400(M-H2O, 3%), 382(M-2H2O, 10.5%), 369(M-H2O-31, 6.3%), 345(M-73, 7.3%), 327(M-H2O-73, 6.6%), 285(M-H2O-SC, 100%)(Ref. 0013)







[0013] / [0237]
198
3a-Hydroxychol-4-en-24-oic Acid
 BBA0198
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

170-172degC(Ref. 0090)
145-147degC (Me ester-3-acetate)(Ref. 0089)
[a]D: +120deg (C=0.8, CHCl3)(Ref. 0090)
[a]D: +175deg (C=0.99, CHCL3) (Me ester-3-acetste)(Ref. 0089)
nmaxm: 9,3-9,4(Ref. 0090)









[0089] / [0090]
199
3b-Hydroxychol-4-en-24-oic Acid
 BBA0199
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

180-182degC, (Me ester; mp,129-131degC)(Ref. 0089/0090)
[a]D: +51deg (C=0.9, dioxane)(Ref. 0089)
[a]D: +48deg (C=1.88, CHCl3) (Me ester)(Ref. 0090)









[0089] / [0090]
200
3a-Hydroxychol-5-en-24-oic Acid
 BBA0200
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

199-200degC, (Me ester; mp, 127degC)(Ref. 0046)
107-109degC (Me ester-3-acetate)(Ref. 0248)
[a]d-21: -25.5deg (C=1.0, CHCl3)(Ref. 0046)
[a]D: -16deg (Me ester)(Ref. 0002)
[a]d-25: +29.9deg (CHCl3) (Me ester-3-acetate)(Ref. 0105)
nmax cm-1: 3430 (OH), 1711, 1670, 1465(Ref. 0046)
Me ester-3-acetate: nmaxcm-1: 860, 870, 1230, 1270, 1730(Ref. 0248)

Me ester-3-acetate(70eV) m/z: 430(M+, 0%), 370(M-AcOH, 100%), 355(M-AcOH-CH3, 12%), 262(8%), 255(M-SC-AcOH, 15%), 249(rings C and D+SC, 26%)(Ref. 0105)







[0002] / [0046] / [0105] / [0248]
201
3b-Hydroxy-chol-5-en-24-oic Acid
 BBA0201
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

218-221degC(Ref. 0042)
147-148degC (Me ester)(Ref. 0094)
[a]D: -36.0deg (C=0.116, EtOH)(Ref. 0042)
[a]d-23: -29.4deg (C=1.0, EtOH) (Me ester)(Ref. 0094)
nmaxcm-1: 1705 (C=O)(Ref. 0042)
Me ester: nmaxcm-1: 3490, 1735, 1710(Ref. 0094)
1H-NMR (CDCl3+MeOH) d: 18-Me 0.71(s), 21-Me 0.96(d), 19-Me 1.02(s), 3a-H 3.20-3.75(m), 6-H 5.20-5.45(brs)(Ref. 0042/0091)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.68(s), 19-Me 1.00(s), 3a-H 3.43(br), COOMe 3.65(s), 6-H 5.34(br)(Ref. 0094)
Me ester-3-acetate 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.69(s), 21-Me 0.94(d), 19-Me 1.03(s), -OCOMe 2.04(s), COOMe 3.68(s), 3a-H 4.06(br), 6-H 5.40(br)(Ref. 0096)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 37.3, C-2 31.7, C-3 71.1, C-4 42.4, C-5 140.7, C-6 121.6, C-7 31.9, C-8 31.9, C-9 50.1, C-10 36.5, C-11 21.1, C-12 39.7, C-13 42.4, C-14 56.7, C-15 24.2, C-16 28.1, C-17 55.8, C-18 11.9, C-19 19.4, C-20 35.4, C-21 18.3, C-22 31.1, C-23 31.1, C-24 174.7, C-25 51.4(Ref. 0244)
Me ester-3-acetate m/z: 430(M+, 0%), 370(M-AcOH, 100%), 355(M-AcOH-CH3, 15%), 262(17%), 255(M-SC-AcOH, 12%), 249(rings C and D+SC, 25%)(Ref. 0105)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from the marine invertebrate Ptilosarcus gurneyi (sea pen).(Ref. 0096)
Identified in human meconium of premature neonates.(Ref. 0146/0148)
Identified in urine of patients suffering acute hepatitis, obstructive jaundice and intermittent jaundice.(Ref. 0147)
Identified in urine and plasma of healthy humans and patients with liver diseases.(Ref. 0150/0151/0152)
A bile acid of the human fetus in early gestation.(Ref. 0156)
A fetal bile acid in urine, meconium, and feces.(Ref. 0180/0194)
Isolated from urine of infants with biliary atresia.(Ref. 0185)
Detected in serum and urine from healthy human adults.(Ref. 0189)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
Excreted in duodenal bile and urine of diabetic patients.(Ref. 0221)
Synthesized from 3b-hydroxy-5-pregnen-20-one.(Ref. 0091)



[0007] / [0042] / [0091] / [0094] / [0096] / [0105] / [0146] / [0147] / [0148] / [0150] / [0151] / [0152] / [0156] / [0180] / [0185] / [0189] / [0192] / [0194] / [0199] / [0202] / [0206] / [0221] / [0244]
202
3a-Hydroxy-5b-chol-6-en-24-oic Acid
 BBA0202
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

218-219degC, (Me ester; mp,104-105degC)(Ref. 0029)
[a]d-20: +17.5pm6deg, [a]d-21: 23.5pm3deg (Me ester)(Ref. 0132)
nmaxcm-1: 1708 (C=O), 3330, 1062 (OH)(Ref. 0029)
1H-NMR (CDCl3+DMSO-d6; 90MHz) d: 18-Me 0.69(s), 19-Me 0.84(s), 21-M 0.93(d), 3b-H 3.52(brm), 6- and 7-H 5.46(s)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.85(s), 21-M 0.93(d), 3b-H 3.53(brm), COOMe 3.66(s), 6- and 7-H 5.46(s)(Ref. 0029)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 34.4, C-2 30.5, C-3 71.1, C-4 40.2, C-5 43.9, C-6 130.6, C-7 128.0, C-8 37.7, C-9 39.8, C-10 33.2, C-11 20.5, C-12 40.8, C-13 43.3, C-14 54.7, C-15 23.9, C-16 28.2, C-17 55.8, C-18 12.0, C-19 22.7, C-20 35.3, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0244)
Me ester-3-acetate m/z: 430(M+, 0%), 370(M-AcOH, 100%), 355(M-AcOH-CH3, 27%), 339(7%), 315(M-SC, 11%), 255(M-SC-AcOH, 26%), 249(rings C and D+SC, 35%), 213(2%), 201(17%)(Ref. 0105)







[0029] / [0105] / [0132] / [0244]
203
3b-Hydroxy-5b-chol-6-en-24-oic Acid
 BBA0203
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

119-120degC (Me ester)(Ref. 0029)
nmaxcm-1: 1740 (C=O), 3280, 1042 (OH)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.70(s), 19-Me 0.89(s), 21-M 0.93(d), COOMe 3.66(s), 3a-H 4.06(m), 6- and 7-H 5.47(s)(Ref. 0029)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 28.9, C-2 27.7, C-3 66.3, C-4 37.5, C-5 38.5, C-6 131.5, C-7 128.0, C-8 37.5, C-9 39.5, C-10 33.6, C-11 20.9, C-12 40.2, C-13 43.3, C-14 54.8, C-15 23.8, C-16 28.2, C-17 55.8, C-18 12.0, C-19 23.8, C-20 35.5, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.5, C-25 51.4(Ref. 0244)








[0029] / [0244]
204
3a-Hydroxy-5b-chol-7-en-24-oic Acid
 BBA0204
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

189-190degC, (Me ester; mp,104-105degC)(Ref. 0072)
[a]d-21: +62.0deg (dioxane)(Ref. 0072)
[a]d-24: +61deg (CHCl3) (Me ester)(Ref. 0104)
Me ester: nmaxcm-1: 3366 (OH), 1738 (C=O), 846 (=C-H)(Ref. 0104)
Me ester 1H-NMR d: 18-Me 0.77(s), 21-M 1.05(d), 19-Me 1.14(s),3b-H 3.70, 7-H 4.72(Ref. 0004)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 34.7, C-2 31.3, C-3 71.1, C-4 37.5, C-5 40.8, C-6 28.6, C-7 115.3, C-8 137.1, C-9 36.6, C-10 33.5, C-11 21.5, C-12 39.8, C-13 43.6, C-14 55.0, C-15 22.7, C-16 27.8, C-17 55.7, C-18 11.8, C-19 24.4, C-20 35.7, C-21 18.3, C-22 30.9, C-23 31.0, C-24 174.5, C-25 51.3(Ref. 0244)
Me ester-3-acetate m/z: 430(M+, 0%), 370(M-AcOH, 100%), 355(M-AcOH-CH3, 35%), 316(M-AcOH-54, 7%), 315(M-SC, 6%), 255(M-SC-AcOH, 30%), 229(12%), 228(13%), 213(26%), 201(M-SC-AcOH-54, 27%)(Ref. 0105)







[0004] / [0072] / [0104] / [0105] / [0244]
205
3b-Hydroxy-5a-chol-7-en-24-oic Acid
 BBA0205
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

110-112degC (Me ester)(Ref. 0098)
[a]d-20: -5.9deg (C=3.73, CHCl3) (Me ester)(Ref. 0098)
[a]d-20: +3.5deg (C=1.02, CHCl3) (3-Acetate)(Ref. 0097)
3-Acetate: nmaxcm-1: 1720 (COOH), 1735 (OCOMe)(Ref. 0097)
3-Acetate 1H-NMR (CCl4; 100MHz) d: 18-Me 0.53(s), 19-Me 0.80(s), 21-M 0.94(d), OCOMe 1.92(s), 3a-H 4.4-4.8(m), 7-H 5.12(m)(Ref. 0097)








[0097] / [0098]
206
3a-Hydroxy-5b-chol-8-en-24-oic Acid
 BBA0206
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

189-190degC, (Me ester; mp,116-117degC)(Ref. 0099)
[a]d-23: +57pm3deg (CHCl3), [a]d-22: +56pm2deg (CHCl3) (Me ester)(Ref. 0099)
lmax (EtOH) (e): 241 (4200) nm(Ref. 0099)









[0099]
207
3a-Hydroxy-5b-chol-8(14)-en-24-oic Acid
 BBA0207
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

167-168degC(Ref. 0106)
81-82degC (Me ester)(Ref. 0002)
[a]d-15: +41pm2deg (CHCl3)(Ref. 0106)
[a]D: +56deg (Me ester)(Ref. 0002)
lmax (EtOH) (e): 214 (5550) nm(Ref. 0106)
Me ester-3-acetate: nmaxcm-1: 1740 (C=O), 1200 (C-O-C)(Ref. 0104)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.770(s), 19-Me 0.799(s), 21-M 0.911(d), 3b-H 3.598(brm, w1/2, 22), COOMe 3.633(s)(Ref. 0071)
Me ester-3-acetate 1H-NMR(CDCl3) d : 18-Me 0.81(s), 19-Me 0.83(s), 21-M 1.00(d), OCOMe 2.00(s), COOMe 3.65(s), 3b-H 4.73(m)(Ref. 0107)Me ester-3-acetate 13C-NMR (CDCl3) d: C-1 34.4, C-2 27.1, C-3 74.2, C-4 34.4, C-5 42.1, C-6 27.1, C-7 28.5, C-8 126.8, C-9 36.0, C-10 36.3, C-11 19.5, C-12 37.3, C-13 42.7, C-14 141.8, C-15 24.7, C-16 27.2, C-17 42.1, C-18 18.1, C-19 23.6, C-20 34.0, C-21 18.8, C-22 31.1, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0107)
Me ester-3-acetate 13C-NMR (CDCl3) d: C-1 34.4, C-2 27.1, C-3 74.2, C-4 34.4, C-5 42.1, C-6 27.1, C-7 28.5, C-8 126.8, C-9 36.0, C-10 36.3, C-11 19.5, C-12 37.3, C-13 42.7, C-14 141.8, C-15 24.7, C-16 27.2, C-17 42.1, C-18 18.1, C-19 23.6, C-20 34.0, C-21 18.8, C-22 31.1, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0107)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 34.6, C-2 30.8, C-3 71.5, C-4 36.0, C-5 42.2, C-6 26.9, C-7 24.7, C-8 126.9, C-9 35.3, C-10 36.0, C-11 19.4, C-12 37.2, C-13 42.6, C-14 141.4, C-15 25.7, C-16 27.3, C-17 56.6, C-18 18.0, C-19 23.6, C-20 33.9, C-21 18.7, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0244)








[0002] / [0071] / [0104] / [0106] / [0107] / [0244]
208
3a-Hydroxy-5b-chol-9(11)-en-24-oic Acid
 BBA0208
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

180-186degC(Ref. 0109)
105degC (Me ester)(Ref. 0108)
[a]d-25: +47pm2deg (dioxan)(Ref. 0109)
[a]D: +44deg (C=1.01, CHCl3) (Me ester)(Ref. 0108)
Me ester 1H-NMR(CDCl3; 500MHz) d: 18-Me 0.535(s), 21-Me 0.874(d), 19-M 1.008(s), 3b-H 3.594(brm, w1/2, 22), COOMe 3.622(s), 11H-5.267(d, J, 6.0)(Ref. 0071)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 35.7, C-2 31.8, C-3 72.2, C-4 38.0, C-5 42.0, C-6 26.9, C-7 26.9, C-8 36.6, C-9 140.0, C-10 38.5, C-11 119.4, C-12 42.0, C-13 40.9, C-14 53.3, C-15 25.3, C-16 28.3, C-17 56.1, C-18 11.6, C-19 29.6, C-20 35.2, C-21 17.9, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0244)








[0071] / [0108] / [0109] / [0244]
209
3b-Hydroxy-5b-chol-9(11)-en-24-oic Acid
 BBA0209
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

174-175degC, (Me ester-3-acetate; mp,178-180degC)(Ref. 0110)
[a]D: +42deg (CHCl3)(Ref. 0110)
[a]d-22: +38deg (dioxane) (Me ester)(Ref. 0001)









[0001] / [0110]
210
3a-Hydroxy-5b-chol-11-en-24-oic Acid
 BBA0210
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

166degC, (Me ester; mp,101-103degC)(Ref. 0111)
[a]d-19: +25.9deg (C=2.2, CHCl3)(Ref. 0111)
[a]16D: +32deg (CHCl3) (Me ester)(Ref. 0001)
nmaxcm-1: 1729 (COOH), 2660, 3420 (OH)(Ref. 0111)
1H-NMR (CDCl3; 100MHz) d: 18-Me 0.72(s), 19-Me 0.88(s), 3b-H 3.65(w1/2 ; 20), -OH 5.74(s), -CH=CH-CH= 2.28, 5.43 and 6.09(AMXm, J, 10.0, 2.0, 3.0)(Ref. 0111)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.647(s), 19-Me 0.800(s), 21-M 0.923(d), 3b-H 3.539(brm, w1/2, 28Hz), COOMe 3.581(s), 12H-5.341(d, J, 10.5), 11-H 6.014(dd, J, 10.0, 2.4)(Ref. 0071)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 35.1, C-2 30.4, C-3 71.5, C-4 37.1, C-5 41.4, C-6 28.0, C-7 25.4, C-8 34.4, C-9 43.1, C-10 34.9, C-11 125.3, C-12 138.6, C-13 44.9, C-14 53.6, C-15 22.9, C-16 28.3, C-17 51.8, C-18 16.6, C-19 23.6, C-20 35.9, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.4(Ref. 0244)
m/z: 374(M+, 9%), 356(100%), 341(35%), 255(45%), 228(40%), 231(25%)(Ref. 0111)
Me ester m/z: 388(M+, 3.5%), 370(56%), 355(20%), 255(56%), 228(35%), 231(25%)(Ref. 0111)
Me ester-3-acetate m/z: 430(M+, 0%), 370(M-AcOH, 47%), 355(M-AcOH-CH3, 19%), 255(M-AcOH-SC, 100%), 228(16%), 213(32%)(Ref. 0105)
CI mass spectrum; Me ester-3-acetate m/z: 431(M+), 371(MH-AcOH)(Ref. 0134)


Isolated from fungal metabolite of a Curvularia species.(Ref. 0111)




[0001] / [0071] / [0105] / [0111] / [0134] / [0244]
211
3a-Hydroxy-5b-chol-14-en-24-oic Acid
 BBA0211
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

171-172degC, (Me ester; mp,141-142degC)(Ref. 0106)
[a]14D: +65pm2deg (CHCl3)(Ref. 0106)
[a]d-20: +52.2deg (CHCl3) (Me ester)(Ref. 0104)
lmax (EtOH) (e): 241 (2270) nm(Ref. 0106)
Me ester : nmaxcm-1: 3299 (OH), 1743 (C=O), 793 (=C-H)(Ref. 0104)
Me ester 1H-NMR(CDCl3; 500MHz) d: 18-Me 0.867(s), 21-Me 0.898(d), 19-M 0.903(s), 3b-H 3.595(brm, w1/2, 23), COOMe 3.646(s), 15H-5.127(brs)(Ref. 0071)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 35.1, C-2 30.7, C-3 71.6, C-4 36.3, C-5 41.9, C-6 26.8, C-7 24.1, C-8 35.2, C-9 40.0, C-10 34.6, C-11 21.8, C-12 42.5, C-13 47.1, C-14 155.1, C-15 116.6, C-16 35.5, C-17 58.3, C-18 16.8, C-19 23.0, C-20 33.5, C-21 18.5, C-22 30.9, C-23 31.0, C-24 174.5, C-25 51.3(Ref. 0244)








[0071] / [0104] / [0106] / [0244]
212
7a-Hydroxy-5b-chol-3-en-24-oic Acid
 BBA0212
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

110-112degC (Me ester)(Ref. 0017)
Me ester: nmaxcm-1: 1737 (COOH), 3553, 1032 (OH)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.67(s), 21-Me 0.92(d), 19-Me 0.97(s), COOMe 3.66(s), 7b-H 3.71(brm), 3- and 4-H 5.70(s)(Ref. 0017)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 33.6, C-2 21.9, C-3 126.7, C-4 132.8, C-5 41.7, C-6 34.4, C-7 69.1, C-8 39.6, C-9 32.8, C-10 33.4, C-11 21.2, C-12 39.4, C-13 42.5, C-14 50.5, C-15 23.5, C-16 28.0, C-17 55.7, C-18 11.7, C-19 22.3, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.2(Ref. 0244)
Me ester-7-acetate m/z: 430(M+, 0%), 370(M-AcOH, 100%), 355(M-AcOH-CH3, 19%), 262(17%), 255(M-SC-AcOH, 24%), 249(rings C and D+SC, 18%), 213(14%)(Ref. 0105)







[0017] / [0105] / [0244]
213
12a-Hydroxy-5b-chol-3-en-24-oic Acid
 BBA0213
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

110-111degC (Me ester)(Ref. 0017)
107-108degC (Me ester-12-acetate)(Ref. 0001)
[a]D: +63.9deg (CHCl3)(Ref. 0001)
[a]d-25: +24.0deg (Me ester)(Ref. 0069)
Me ester: nmaxcm-1: 1740 (C=O), 3202, 1030, 975 (OH)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.70(s), 19-Me 0.94(s), 21-Me 0.97(d), COOMe 3.66(s), 12b-H 3.97(brm), 4-H 5.70(m), 3-H 5.60(m)(Ref. 0017)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 33.7, C-2 22.6, C-3 127.0, C-4 131.9, C-5 43.3, C-6 25.5, C-7 27.3, C-8 35.7, C-9 34.0, C-10 32.9, C-11 29.4, C-12 73.1, C-13 46.4, C-14 48.0, C-15 23.6, C-16 27.1, C-17 47.1, C-18 12.6, C-19 22.1, C-20 35.0, C-21 17.2, C-22 30.8, C-23 30.9, C-24 174.4, C-25 51.2(Ref. 0244)
Me ester-12-acetate m/z: 430(M+, 0%), 370(M-AcOH, 35%), 355(M-AcOH-CH3, 11%), 316(M-AcOH-54, 96%), 255(M-SC-AcOH, 100%), 228(10%), 213(15%), 201(M-AcOH-SC-54, 49%)(Ref. 0105)







[0001] / [0017] / [0069] / [0105] / [0244]
214
3b,6b-Dihydroxychol-4-en-24-oic Acid
 BBA0214
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

229-232degC, (Me ester; mp, 194-195degC)(Ref. 0112)
[a]d-19: +0pm2deg (C=0.913, pyridine), [a]d-22: +22pm2deg (C=0.948) (Me ester)(Ref. 0112)
lmax (EtOH) (e): 205.5(5800) nm(Ref. 0112)
nmaxcm-1: 1706 (C=O), 3000 (OH), 1658 (C=C)(Ref. 0112)









[0112]
215
3a,7a-Dhiydroxychol-4-en-24-oic Acid
 BBA0215
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

143-144degC (Me ester)(Ref. 0113)
Me ester: nmaxcm-1: 1750(C=O), 3200 (OH), 1000 (C-O)(Ref. 0113)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.67(s), 19-Me 0.96(s), COOMe 3.59(s), 7b-H 3.73(m), 3b-H 3.98(m), 4-H 5.51(d, J, 5.0)(Ref. 0113)
Me ester (20eV) m/z: 386(M-H2O), 368(M-2H2O)(Ref. 0113)


Isolated from bladder bile of hens.(Ref. 0113)




[0113]
216
3b,7a-Dihydroxychol-4-en-24-oic Acid
 BBA0216
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

229-231degC(Ref. 0114)
143-145degC (Me ester)(Ref. 0113)
[a]d-23: +40.8pm0.5deg (C=0.25, MeOH)(Ref. 0114)
[a]d-23: +17deg (MeOH) (Me ester)(Ref. 0113)

Methoxylated Me ester (20eV) m/z: 400(100%), 368, 353, 253, 249, 138, 135(Ref. 0115)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from bladder bile of hens.(Ref. 0113/0114)
Isolated from the fistula bile of patients with cholestasis.(Ref. 0115)
A biotransformation product of 7a-hydroxycholesterol in the hen.(Ref. 0214)




[0007] / [0113] / [0114] / [0115] / [0214]
217
3b,7a-Dihydroxychol-5-en-24-oic Acid
 BBA0217
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

206-210degC, (Me ester; mp, 161-163degC)(Ref. 0114/0241)
[a]d-24: -82deg (MeOH)(Ref. 0114/0241)
[a]D: -85deg (MeOH) (Me ester)(Ref. 0241)
nmaxcm-1: 2600, 1710 (COOH), 3510, 3250 (OH)(Ref. 0095)
1H-NMR (Pyridine-d5; 90MHz) d: 18-Me 0.71(s), 19-Me 0.99(s), 3a-H 3.70(m), 7b-H 4.12(m), 6-H 5.83(d, J, 7.0)(Ref. 0095)
Me ester 1H-NMR (CDCl3; 60MHz) d: 18-Me 0.68(s), 19-Me 0.98(s), COOMe 3.67(s), 6-H 5.59(d, J, 6.0)(Ref. 0004/0241)
Me-TMS ether (70eV) m/z: 458(100%), 368(1%), 253(2%)(Ref. 0007/0095/0117)


Isolated from bladder bile of hens and rats.(Ref. 0113/0213)
Isolated from human bile.(Ref. 0115)
Isolated from urine of a 3-mo-old boy with cholestatic jaundice.(Ref. 0117)
Isolated from duodental bile, urine, plasma, and feces of a child with hepatic 3b-hydroxy D5-C27-steroid dehydrogenase deficiency.(Ref. 0174)
A biotransformation product of 7a-hydroxycholesterol in the hen.(Ref. 0214)




[0004] / [0007] / [0095] / [0113] / [0114] / [0115] / [0117] / [0174] / [0213] / [0214] / [0241]
218
3b,7b-Dihydroxychol-5-en-24-oic Acid
 BBA0218
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

220-223degC, (Me ester; mp, 144-146degC)(Ref. 0114/0241)
[a]d-24: +12deg (MeOH)(Ref. 0114/0241)
[a]D: +17.8deg (MeOH) (Me ester)(Ref. 0241)
nmaxcm-1: 2570, 1725, 1700 (COOH), 3470, 3200 (OH)(Ref. 0095)
1H-NMR (Pyridine-d5; 90MHz) d: 18-Me 0.70(s), 19-Me 0.95(s), 3a-H 3.67(m), 7a-H 3.92(d, J, 9.0), 6-H 5.48(bs)(Ref. 0095)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.70(s), 19-Me 1.05(s), COOMe 3.68(s), 6-H 5.35(s)(Ref. 0004/0241)
Me ester-3-acetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.658(s), 19-Me 0.896(s), 21-M 1.023(d), OCOMe 1.998(s), COOMe 3.627(s), 3a-H 4.582(brm, w1/2, 24), 6H-5.275(brs)(Ref. 0071)
Me ester-3-acetate 13C-NMR(CDCl3; 22.53MHz) d: C-1 36.6, C-2 27.7, C-3 73.4, C-4 37.6, C-5 142.3, C-6 126.3, C-7 73.1, C-8 40.8, C-9 48.2, C-10 36.6, C-11 21.0, C-12 39.5, C-13 43.0, C-14 55.1, C-15 26.3, C-16 28.4, C-17 55.9, C-18 11.8, C-19 19.0, C-20 35.3, C-21 18.4, C-22 31.1, C-23 31.1, C-24 174.5, C-25 51.4(Ref. 0244)
Me-TMS ether (70eV) m/z: 458(100%), 368(2%), 253(0%)(Ref. 0095)


Identified in human urine of patients with extra- or intrahepatic cholestasis.(Ref. 0187)




[0004] / [0071] / [0095] / [0114] / [0187] / [0241] / [0244]
219
3b,12a-Dihydroxychol-5-en-24-oic Acid
 BBA0219
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

253-254degC(Ref. 0095)
nmaxcm-1: 1700 (COOH), 3435, 3300 (OH)(Ref. 0095)
1H-NMR(CD3OD; 90MHz) d: 18-Me 0.82(s), 19-Me 0.99(s), 3a-H 3.20-3.66(m), 12b-H 3.99(t, J, 3.0)(Ref. 0095)
Me-TMS ether (70eV) m/z: 458(13%), 368(23%), 253(100%)(Ref. 0095)


Identified in human meconium.(Ref. 0148)
Identified in urine and serum of healthy humans and patients with liver diseases.(Ref. 0150/0151/0189)
Excreted in urine or serum of a healthy newborn and an infant with liver diseases.(Ref. 0194/0207)
Identified in human umbilical cord blood and amniotic fluid from newborns and in sera and urine from adult patients with cholestatic liver diseases.(Ref. 0199)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)




[0095] / [0148] / [0150] / [0151] / [0189] / [0194] / [0199] / [0202] / [0206] / [0207]
220
3a,12a-Dihydroxy-5b-chol-6-en-24-oic Acid
 BBA0220
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

188degC(Ref. 0132)
86.5-87.5degC (Me ester-3-acetate)(Ref. 0105)
[a]d-21: +36pm2deg (C=1.0)(Ref. 0132)
nmaxcm-1: 1695 (C=O), 3362 (OH)(Ref. 0034)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 19-Me 0.81(s), 21-Me 1.00(d), 3b-H 3.39(brm), 12b-H 3.95(m), 6- and 7-H 5.45(s)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 19-Me 0.84(s), 21-Me 0.99(d), 3b-H 3.57(brm), COOMe 3.67(s), 12b-H 4.00(m), 6- and 7-H 5.47(s)(Ref. 0034)
Me ester-3,12-diacetate 13C-NMR(CDCl3; 22.53MHz) d: C-1 33.7, C-2 26.5, C-3 73.2, C-4 35.9, C-5 43.4, C-6 130.5, C-7 127.3, C-8 37.4, C-9 33.3, C-10 32.6, C-11 25.2, C-12 75.6, C-13 45.6, C-14 48.0, C-15 23.0, C-16 27.3, C-17 47.3, C-18 12.1, C-19 22.2, C-20 34.6, C-21 17.4, C-22 30.8, C-23 30.9, C-24 174.2, C-25 51.3(Ref. 0244)
Me ester-3,12-diacetate m/z: 488(M+, 0%), 428(M-AcOH, 23%), 368(M-2AcOH, 36%), 353(M-2AcOH-CH3, 13%), 314(M-2AcOH-54, 20%), 313(M-SC-AcOH, 74%), 253(M-SC-2AcOH, 100%), 247(rings C and D+SC, 4%), 226(15%), 211(19%)(Ref. 0105)







[0034] / [0105] / [0132] / [0244]
221
3a,12b-Dihydroxy-5b-chol-6-en-24-oic Acid
 BBA0221
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

[a]d-25: +28.1deg (C=0.64) (Me ester)(Ref. 0062)
Me ester: nmaxcm-1: 1740 (C=O), 3400, 1002 (OH)(Ref. 0062)
Me ester 1H-NMR (CDCl3+DHSO-d6; 400MHz) d: 18-Me 0.72(s), 19-Me 0.87(s), 21-Me 1.00(d, J=5.4Hz), 3b- and 12a-H 3.50(bm), COOMe 3.67(s), 6- and 7-H 5.45(s)(Ref. 0062)
Me-TMS ether (70eV) m/z: 273(35.6%), 253(100%), 281(2.9%), 343(45.0%), 368(12.6%), 458(12.6%), 533(1.7%)(Ref. 0062)







[0062]
222
3a,12a-Dihydroxy-5b-chol-7-en-24-oic Acid
 BBA0222
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

210-212degC, (Me ester; mp, 64-67degC)(Ref. 0116)
68-70degC (Me ester-3,12-diacetate)(Ref. 0230)
[a]d-23: +92.6pm2deg (C=1.572, dioxane)(Ref. 0116)
[a]d-18: +78.3pm2deg (C=1.495,CHCl3) (Me ester)(Ref. 0116)
Me ester-3,12-diacetate: nmaxcm-1: 1725(COOMe), 1250, 1738(OCOMe)(Ref. 0230)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.506(s), 19-M 0.777(s), 21-Me 0.919(d), 3b-H 3.515(brm, w1/2, 23), COOMe 3.608(s), 12b-H 4.003(t, J, 2.1), 7-H 5.053(d, J, 3.5)(Ref. 0071)
Me ester-3,12-diacetate 1H-NMR (CDCl3) d: 18-Me 0.63(s), 19-Me 0.85(s), 3a- and 12a-OCOMe 2.00, 2.10(each s), 23-H2 2.3(m), COOMe 3.61(s), 3b-H 4.87, 12b-H 5.13(Ref. 0230)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 34.6, C-2 31.2, C-3 71.7, C-4 37.6, C-5 40.9, C-6 28.7, C-7 2115.9, C-8 137.0, C-9 30.9, C-10 33.2, C-11 29.2, C-12 72.8, C-13 47.6, C-14 46.5, C-15 22.3, C-16 27.2, C-17 47.1, C-18 12.8, C-19 24.2, C-20 35.6, C-21 17.5, C-22 30.9, C-23 31.2, C-24 174.5, C-25 51.4(Ref. 0244)
Me ester-3,12-diacetate m/z: 488(M+, 0%), 428(M-AcOH, 30%), 368(M-2AcOH, 38%), 353(M-2AcOH-CH3, 11%), 338(9%), 314(M-2AcOH-54, 32%), 313(M-SC-AcOH, 100%), 286(2%), 253(M-SC-2AcOH, 100%), 226(25%), 211(19%)(Ref. 0105/0230)
Me ester-3,12-diacetate (70eV) m/z: 488(M, 1%), 428(M-AcOH, 24%), 368(M-2AcOH, 38%), 313(M-SC, 76%), 253(100%), 211(24%), 413(4%), 353(9%), 286(5%), 281(8%), 226(24%)(Ref. 0231)







[0071] / [0105] / [0116] / [0230] / [0231] / [0244]
223
3a,12a-Dihydroxy-5b-chol-8-en-24-oic Acid
 BBA0223
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

196-198degC(Ref. 0001)
[a]D: +6deg(CHCl3)(Ref. 0001)









[0001]
224
Apocholic Acid
3a,12a-Dihydroxy-5b-chol-8(14)-en-24-oic Acid
 BBA0224
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

168-172degC, (Me ester; mp, 80-83degC)(Ref. 0107/0253)
137-137.5degC (Me ester-3,12-diacetate)(Ref. 0235)
[a]D: +38.4deg (C=0.727, dioxane), [a]D: +34.64deg (C=1.25, dioxane) (Me ester)(Ref. 0107/0253)
[a]14D: +86.1deg (C=2.512, CHCl3) (Me ester-3,12-diacetate)(Ref. 0253)
nmax(CHCl3)cm-1: 3400, 1690(Ref. 0058)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.86(s), 19-Me 0.82(s), 21-M 0,975(d), COOMe 3.63(s), 12b-H 3.90(t)(Ref. 0107)
Me ester 13C-NMR (CDCl3) d: C-1 34.6, C-2 30.9, C-3 71.6, C-4 36.1, C-5 42.3, C-6 26.6, C-7 26.3, C-8 127.4, C-9 31.3, C-10 36.2, C-11 26.5, C-12 72.0, C-13 47.4, C-14 138.1, C-15 24.7, C-16 27.4, C-17 47.4, C-18 19.3, C-19 24.0, C-20 33.9, C-21 17.7, C-22 31.1, C-23 30.9, C-24 174.7, C-25 51.5(Ref. 0107/0244)
m/z: 372(M-H2O), 354(M-2H2O), 271, 253(100%)(Ref. 0058)
Me ester-3,12-diacetate m/z: 488(M+, 0%), 428(M-AcOH, 29%), 413(M-AcOH-CH3, 11%), 368(M-2AcOH, 21%), 353(M-2AcOH-CH3, 16%), 314(M-2AcOH-54, 30%), 313(M-SC-AcOH, 88%), 286(25%), 253(M-SC-2AcOH, 100%), 226(49%), 211(21%)(Ref. 0105)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0007] / [0058] / [0105] / [0107] / [0235] / [0244] / [0253]
225
3a,12a-Dihydroxy-5b-chol-9(11)-en-24-oic Acid
 BBA0225
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

138-140degC, (Me ester; mp, 79-81degC)(Ref. 0087)
[a]d-23: +89.0pm1deg (C=2.180, EtOH), [a]d-21: +88.4pm1.5deg (C=1.388, EtOH) (Me ester)(Ref. 0087)
Me ester-3,12-diacetate 1H-NMR (CCl4) d: 5.65(d, J, 6.0)(Ref. 0105)
Me ester-3,12-diacetate m/z: 488(M+, 0%), 428(M-AcOH, 13%), 413(M-AcOH-CH3, 4%), 386(5%), 368(M-2AcOH, 12%), 353(M-2AcOH-CH3, 14%), 314(M-2AcOH-54, 33%), 313(M-SC-AcOH, 97%), 286(11%), 253(M-SC-2AcOH, 100%), 226(49%)(Ref. 0105)







[0087] / [0105]
226
7a,12a-Dihydroxy-5b-chol-3-en-24-oic Acid
 BBA0226
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

136-137degC (Me ester)(Ref. 0017)
Me ester: nmaxcm-1: 1743 (C=O), 3405, 990 (OH)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.96(s), 21-Me 0.99(d), COOMe 3.66(s), 7b-H 3.70(m), 12b-H 3.98(m), 3- and 4-H 5.70(s)(Ref. 0017)
Me ester-3,12-diacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.671(s), 21-M 0.748(d), 19-Me 0.878(s), OCOMe 1.941 and 2.007(s), COOMe 3.582(s), 7b-H 4.758(m, w1/2, 7), 12b-H 5.001(t, J, 1.9), 4-H 5.233(dd, J, 10.0, 1.3), 3-H 5.446(brm, w1/2, 20)(Ref. 0071)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 33.5, C-2 21.7, C-3 126.8, C-4 132.5, C-5 42.3, C-6 34.4, C-7 69.0, C-8 39.5, C-9 26.5, C-10 33.2, C-11 28.9, C-12 72.8, C-13 46.3, C-14 41.6, C-15 22.9, C-16 27.3, C-17 47.2, C-18 12.6, C-19 22.1, C-20 35.0, C-21 17.2, C-22 30.8, C-23 30.9, C-24 174.5, C-25 51.4(Ref. 0244)








[0017] / [0071] / [0244]
227
3b,7a,12a-Trihydroxychol-5-en-24-oic Acid
 BBA0227
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file


Me-TMS ether (22.5eV) m/z: 548(M-TMSOH, 100%), 456, 366, 341, 251, 247(Ref. 0007/0117)


Isolated from urine of a 3-mo-old boy with cholestatic jaundice.(Ref. 0117)
Isolated from duodenal bile, urine, plasma, and feces of a child with hepatic 3b-hydroxy D5-C27-steroid dehydrogenase deficiency.(Ref. 0174)
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)




[0007] / [0117] / [0174] / [0202]
228
D22-chenodeoxycholic Acid
(22E)-3a,7a-Dihydroxy-5b-chol-22-en-24-oic Acid
 BBA0228
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

OIL (Me ester)(Ref. 0139)
Et ester; acetonitrile: lmax (e) : 216(10700) nm(Ref. 0249)
Me ester: nmaxcm-1: 1650 (D22), 1730 (COOCH3), 3400 (OH)(Ref. 0139)t ester: nmaxcm-1: 1610 (C=C), 1670 (C=O), 3400 (OH)(Ref. 0249)
Me ester 1H-NMR (Pyridine-d5) d: 0.68 (3H, s, 18-CH3), 0.95 (3H, s, 19-CH3), 1.03 (3H, d, J=6Hz, 21-CH3), 3.65 (3H, s, COOCH3), 3.60 (1H, m, 3b-H), 3.93 (1H, m, 7b-H), 5.82 (1H, d, J=15.3Hz, 23-H), 6.89 (1H, dd, J=15.3 and 7.2Hz, 22-H)(Ref. 0139)
Et ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.92(s), 21-Me 1.10(d), 24-COOCH2CH3 1.29(t, J, 7.0), 3b-H 3.49(brm), 7b-H 3.87(m), 24-COOCH2CH3 4.20(dq, J, 7.0, 3.0), 22-H 5.67(ddd, J, 16.0, JCH, 160), 22-H 6.94(dd, J, 7.0, 16.0)
Et ester 13C-NMR (CDCl3; 22.53MHz) d: C23 118.7, C24 167.2(Ref. 0249)
Me-TMS ether m/z: 458(M-90, 4%), 443(M-15-90, 3%), 368(M-2x90, 100%), 353(M-15-2x90, 15%), 255(M-2x90-SC, 32%), 243(C-3-C-7, 8%)(Ref. 0139)
Et ether m/z: 374[(M+2)-TMSOH], 384[(M+2)-2TMSOH], 255(M-2TMSOH-SC)(Ref. 0249)







[0139] / [0249]
229
D22-ursodeoxycholic Acid
(22E)-3a,7b-Dihydroxy-5b-chol-22-en-24-oic Acid
 BBA0229
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

229-230degC(Ref. 0139)
Me ester : nmaxcm-1 : 1650 (D22), 1730 (COOCH3), 3400 (OH)(Ref. 0139)
Me ester 1H-NMR (Pyridine-d5) d: 0.69 (3H, s, 18-CH3), 0.95 (3H, s, 19-CH3), 1.06 (3H, d, J=6Hz, 21-CH3), 3.65 (3H, s, COOCH3), 3.75 (2H, m, 3b- and 7a-H), 5.85 (1H, d, J=15.3Hz, 23-H), 6.95 (1H, dd, J=15.3 and 7.2Hz, 22-H)(Ref. 0139)
Me-TMS ether m/z: 621(M-15, 16%), 458(M-90, 100%), 443(M-15-90, 9%), 368(M-2x90, 26%), 353(M-15-2x90, 13%), 345(M-90-SC, 8%), 255(M-2x90-SC, 49%), 243(C-3-C-7, 20%)(Ref. 0139)







[0139]
230
D22-deoxycholic Acid
(22E)-3a,12a-Dihydroxy-5b-chol-22-en-24-oic Acid
 BBA0230
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

98-100degC (Me ester)(Ref. 0139)
Me ester: nmaxcm-1: 1640 (D22), 1720 (COOCH3), 3400 (OH)(Ref. 0139)
Me ester 1H-NMR (Pyridine-d5) d: 0.73 (3H, s, 18-CH3), 0.94 (3H, s, 19-CH3), 1.23 (3H, d, J=6Hz, 21-CH3), 3.65 (3H, s, COOCH3), 3.80 (1H, m, 3b-H), 4.07 (1H, m, 12b-H), 5.85 (1H, d, J=15.3Hz, 23-H), 6.98 (1H, dd, J=15.3 and 7.2Hz, 22-H)(Ref. 0139)
Me-TMS ether m/z: 548 (M+, 13%), 533 (M-15, 19%), 458(M-90, 8%), 368(M-2x90, 11%), 353(M-15-2x90, 7%), 345(M-90-SC, 17%), 255(M-2x90-SC, 100%)(Ref. 0139)







[0139]
231
D22-b-muricholic Acid
(22E)-3a,6b,7b-Trihydroxy-5b-chol-22-en-24-oic Acid
 BBA0231
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

Me ester 1H-NMR (Pyridine-d5; 399.950MHz) d: 18-Me 0.672(s), 21-Me 1.076(d), 19-Me 1.450(s), COOMe 3.731(s), 7a-H 3.780(dd, J, 10.5, 3.5), 6a-H 4.064(dd, J, 4.0, 2.0), 23-H 5.978(dd, J, 15.5, 0.6), 22-H 7.080(dd, J, 15.5, 9.0)(Ref. 0118)
Me ester 13C-NMR (taurine conjugate; Pyridine-d5; 50.309MHz) d: C1 36.51, C2 31.08, C3 70.74, C4 36.88, C5 48.85, C6 76.47, C7 73.37, C8 39.20, C9 40.22, C10 34.49, C11 21.27, C12 40.22, C13 44.06, C14 56.06, C15 27.84, C16 28.91, C17 54.56, C18 12.58, C19 26.26, C20 39.89, C21 19.57, C22 155.40, C23 119.14, C24 167.31, C25 51.24(Ref. 0118)
1H-NMR (Taurine conjugate; Pyridine-d5; 399.950MHz) d: 18-Me 0.672(s), 21-Me 1.051(d), 19-Me 1.421(s), 7a-H 3.763(dd, J, 10.0, 3.7), 6a-H 4.053(dd, J, 3.2, 2.2), 23-H 6.086(d, J, 15.3), 22-H 7.047(dd, J, 15.3, 8.8), CH2S 3.531(t, J, 6.7), CH2N 4.332(t, J, 6.0), NH 8.705(t, J, 5.8)(Ref. 0118)
13C-NMR (taurine conjugate; Pyridine-d5; 50.309MHz) d: C1 36.50, C2 31.05, C3 70.75, C4 36.84, C5 48.80, C6 76.46, C7 73.35, C8 39.14, C9 40.24, C10 34.47, C11 21.27, C12 40.24, C13 43.95, C14 56.11, C15 27.82, C16 29.10, C17 54.85, C18 12.56, C19 26.25, C20 39.69, C21 19.95, C22 149.50, C23 122.82, C24 166.59, C25 51.24, CH2S 51.65, CH2N 36.74(Ref. 0118)



Primary bile acid in rats.(Ref. 0102)
A biotransformation product of b-muricholic acid in rats with an intestinal bacteria obtained from human feces.(Ref. 0118)
Identified as a major bile acid in human and rat liver tissue and in hepatocyte nuclei.(Ref. 0197)
Identified in the serum of female rats.(Ref. 0208)




[0102] / [0118] / [0197] / [0208]
232
22-Dehydrochocholic Acid
(22E)-3a,7a,12a-Trihydroxy-5b-chol-22-en-24-oic Acid
 BBA0232
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

181-183degC (Me ester)(Ref. 0139)
Me ester : nmaxcm-1 : 1650 (D22), 1730 (COOCH3), 3400 (OH)(Ref. 0139)
Me ester 1H-NMR (Pyridine-d5) d: 0.78 (3H, s, 18-CH3), 0.97 (3H, s, 19-CH3), 1.28 (3H, d, J=6Hz, 21-CH3), 3.65 (3H, s, COOCH3), 3.60 (1H, m, 3b-H), 3.98 (1H, m, 7b-H), 4.09 (1H, m, 12b-H), 5.82 (1H, d, J=15.3Hz, 23-H), 6.95 (1H, dd, J=15.3 and 7.2Hz, 22-H)(Ref. 0139)
Me-TMS ether m/z: 636(M+, 4%), 621(M-15, 7%), 546(M-90, 14%), 531(M-15-90, 5%), 456(M-2x90, 39%), 441(M-15-2x90, 7%), 366(M-3x90, 32%), 351(M-15-3x90, 20%), 433(M-90-SC, 4%), 343(M-2x90-SC, 24%), 253(M-3x90-SC, 100%), 243(C-3-C-7, 8%)(Ref. 0139)







[0139]
233
3-Oxochol-4-en-24-oic Acid
 BBA0233
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

184-186degC(Ref. 0092)
125-126degC (Me ester)(Ref. 0090)
[a]d-21: +61deg (CHCl3) (Me ester)(Ref. 0104)
lmax (EtOH) (e) : 240 (16500) nm(Ref. 0093)
Me ester : nmaxcm-1 : 3030, 1745, 1680, 1620 cm-1(Ref. 0093/0104)
1H-NMR (CDCl3) d: 0.72 (3H, s, 18-CH3), 0.94 (3H, d, J=6Hz, 21-CH3), 1.19 (3H, s, 19-CH3), 5.74 (1H, s, 4-H)(Ref. 0092)
Me ester 1H-NMR (CDCl3; 200MHz) d: 18-Me 0.72(s), 21-Me 0.92(d), 19-Me 1.17(s), COOMe 3.62(s), 4-H 5.66(s)(Ref. 0093)
Me ester 13C-NMR (CDCl3; 50MHz) d: C-1 35.7, C-2 33.9, C-3 199.4, C-4 123.8, C-5 171.4, C-6 32.9, C-7 32.0, C-8 35.7, C-9 53.7, C-10 38.6, C-11 21.0, C-12 39.6, C-13 42.5, C-14 55.9, C-15 24.1, C-16 28.0, C-17 55.9, C-18 11.9, C-19 17.4, C-20 35.3, C-21 18.2, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0093/0251)
Me ester m/z: 386 [M+] (17), 271 (3), 263 (6), 244 (5), 229 (26), 124 (100)(Ref. 0093)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


Isolated from human faeces.(Ref. 0205)




[0007] / [0090] / [0092] / [0093] / [0104] / [0205] / [0251]
234
3-Oxochola-1,4-dien-24-oic Acid
 BBA0234
Takashi Iida
C24H34O3 370.525 Download ChemDraw structure file

224-226degC(Ref. 0120)
131-133degC (Me ester)(Ref. 0119)
[a]d-22: +25deg (C=1.0, CHCl3) (Me ester)(Ref. 0119)
Me ester : lmax (e) : 244.0 (11700) nm(Ref. 0121)
Me ester : nmaxcm-1 : 1734 (C=O), 1600, 1625, 1665, (D1.4-3-OXO)(Ref. 0121)
Me ester 1H-NMR (CDCl3; 200MHz) d: 18-Me 0.75(s), 21-Me 0.93(d), 19-Me 1.23(s), COOMe 3.65(s), 4-H 6.07(s), 2-H 5.85(d, J, 10.0), 1-H 6.80(d, J, 10.0)(Ref. 0093)
Me ester 13C-NMR (CDCl3; 50MHz) d: C-1 155.9, C-2 127.5, C-3 186.3, C-4 123.8, C-5 169.3, C-6 33.6, C-7 32.9, C-8 35.5, C-9 52.3, C-10 43.5, C-11 22.8, C-12 39.4, C-13 42.7, C-14 55.4, C-15 24.3, C-16 27.9, C-17 55.7, C-18 12.0, C-19 18.7, C-20 35.2, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.4(Ref. 0093/0251)
m/z: 370(M+), 355 (M-CH3), 269(M-SC), 122(100%)(Ref. 0120)
Me ester m/z: 384(M+), 369 (M-SC), 122(100%)(Ref. 0120)







[0093] / [0119] / [0120] / [0121] / [0251]
235
3-Oxochola-4,6-dien-24-oic Acid
 BBA0235
Takashi Iida
C24H34O3 370.525 Download ChemDraw structure file

197-198degC(Ref. 0023)
l max (e): 284 (30500) nm(Ref. 0023)
1710 (C=O), 1628, 1608, (4,6-DIENE)(Ref. 0023)
1H-NMR (CDCl3) d: 0.77 (3H, s, 18-CH3), 0.95 (3H, d, J=5.4Hz, 21-CH3), 1.11 (3H, s, 19-CH3), 5.69 (1H, s, 4-H), 6.12 (2H, s, 6- and 7-H)(Ref. 0023)
Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 33.8, C-2 33.8, C-3 199.1, C-4 123.4, C-5 163.6, C-6 127.7, C-7 141.1, C-8 37.6, C-9 50.6, C-10 36.0, C-11 20.5, C-12 39.4, C-13 43.3, C-14 53.3, C-15 23.6, C-16 27.9, C-17 55.6, C-18 11.8, C-19 16.2, C-20 35.2, C-21 18.1, C-22 30.9, C-23 31.0, C-24 174.2, C-25 51.3(Ref. 0251)
Me-DMES-methoxime (70eV) m/z: 413(M+, 100%), 382(M-31, 35%), 298(M-SC), 249(88%)(Ref. 0204)


Detected in chiken bile.(Ref. 0101)
A biotransformation product of chenodeoxycholic acid by Pseudomonas species NCIB 10590.(Ref. 0195)
A major bile acid identified in urine and serum of infants with cholestasis.(Ref. 0204)




[0023] / [0101] / [0195] / [0204] / [0251]
236
3,12-Dioxochol-4-en-24-oic Acid
 BBA0236
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

199-201degC, (Me ester; mp, 142-144degC)(Ref. 0001)
196-198degC (Me ester)(Ref. 0125)
Me ester: lmax (MeOH) (loge): 241 (4.17) nm(Ref. 0125)
Me ester: nmaxcm-1: 1736, 1706, 1665, 1624(Ref. 0125)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.88(s), 21-Me 1.13(d), 19-M 1.20(s), COOMe 3.68(s), 4-H 5.73(s), 6- and 7-H 6.14(s)(Ref. 0004)
Me ester m/z: 400(9%), 285(16%), 124(100%)(Ref. 0125)


A microbial degradation product of deoxycholic acid by Pseudomonas sp NCIB 10590.(Ref. 0125)




[0001] / [0004] / [0125]
237
3a-Hydroxy-12-oxo-5b-chol-9(11)-en-24-oic Acid
 BBA0237
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

180-180.5degC, (Me ester; mp, 119.5-120degC)(Ref. 0122)
[a]D: +107pm2deg (C=1.0, MeOH), [a]D: +107pm2deg (C=1.0, MeOH) (Me ester)(Ref. 0122)
lmax (loge): 240 (4.070) nm(Ref. 0122)
Me ester: lmax (loge): 240 (4.077) nm(Ref. 0122)
Me ester-3-acetate: nmaxcm-1: 1740, 1730, 1680 (C=O), 1245 (C-O-C)(Ref. 0104)

Me ester-3-acetate m/z: 444(M+, 30%), 384(M-AcOH, 16%), 369(M-AcOH-CH3, 6%), 229(87%), 121(100%)(Ref. 0105)







[0104] / [0105] / [0122]
238
3b-Hydroxy-12-oxo-5b-chol-9(11)-en-24-oic Acid
 BBA0238
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

113-114degC (Me ester)(Ref. 0078)
[a]d-20: +92pm1deg (C=1.0, CHCl3) (Me ester)(Ref. 0078)
nmaxcm-1: 1731, 1440, 1175 (COOMe), 1674, 1307 (>C=O), 3620, 1035(OH)(Ref. 0078)
Me ester 1H-NMR(CDCl3) d: 18-Me 0.92(s), 19-Me 1.22(s), COOMe 3.65(s), 3a-H 4.10(m), 11-H 5.70(d, J, 2.1)(Ref. 0078)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)


A microbial degradation product of deoxycholic acid by Pseudomonas sp NCIB 10590.(Ref. 0125)




[0007] / [0078] / [0125]
239
7a-Hydroxy-3-oxochol-4-en-24-oic Acid
 BBA0239
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

227-229degC(Ref. 0123)
[a]d-22: +61deg (C=0.86, MeOH)(Ref. 0001)
l max (e): 242 (15900) nm(Ref. 0023)
1718 (C=O), 1630 (4-ENE), 3500 (OH)(Ref. 0023)
1H-NMR (CDCl3+20%DMSO-d6) d: 0.71 (3H, s, 18-CH3), 0.93 (3H, d, J=5.4Hz, 21-CH3), 1.19 (3H, s, 19-CH3), 3.91 (1H, m, 7b-H), 5.70 (1H, s, 4-H)(Ref. 0023)
Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 35.3, C-2 33.9, C-3 198.7, C-4 126.6, C-5 167.9, C-6 41.0, C-7 68.2, C-8 39.2, C-9 45.0, C-10 38.4, C-11 20.8, C-12 39.8, C-13 42.4, C-14 50.3, C-15 23.5, C-16 28.0, C-17 55.7, C-18 11.8, C-19 17.0, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.4(Ref. 0251)
m/z: 402(M+, 51%), 384(M-H2O, 50%), 374(M-28, 26%), 369(M-CH3-H2O, 17%), 366(M-2H2O, 12%), 346(M-56, 57%), 269(M-H2O-SC, 25%), 261[M-(H2O+ring+C-6), 14%], 249[M-(rings A+B), 20%], 227(M-H2O-SC-ring D, 18%), 124[ring A+(C-6+C-19), 100%](Ref. 0123)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)
Me-DMES-methoxime (70eV) m/z: 517(M+, 30%), 488(M-31, 47%), 413(M-104), 382(M-104-31, 100%)(Ref. 0204)


A major bile acid identified in urine and serum of infants with cholestasis.(Ref. 0204)




[0001] / [0007] / [0023] / [0123] / [0204] / [0251]
240
12a-Hydroxy-3-oxochol-4-en-24-oic Acid
 BBA0240
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

235-238degC, (Me ester; mp, 150.0-151.5degC)(Ref. 0014)234-235degC (Me ester)(Ref. 0125)
Me ester: lmax (MeOH) (loge): 241 (4.18) nm(Ref. 0125)
nmaxcm-1: 1695, 1630 (C=O), 1610(d4), 3470, 1042, 975, 957 (OH)(Ref. 0014)
Me ester: nmaxcm-1: 3460, 1735, 1660, 1618(Ref. 0125)
1H-NMR (CDCl3; 100MHz) d: 18-Me 0.70(s), 21-Me 0.97(d), 19-Me 1.15(s), 12b-H 3.96(brs), 4-H 5.64(s)(Ref. 0081)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.74(s), 21-Me 0.99(d), 19-Me 1.18(s), COOMe 3.63(s), 12b-H 4.01(m), 4-H 5.66(s)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.79(s), 19-Me 1.05(s), 21-Me 1.30(d), COOMe 3.72(s), 12b-H 4.11(t, J, 3.0), 4-H 5.77(s)(Ref. 0125)
Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 35.5, C-2 33.9, C-3 199.3, C-4 123.8, C-5 171.1, C-6 32.9, C-7 31.7, C-8 35.8, C-9 47.2, C-10 38.1, C-11 28.7, C-12 72.5, C-13 46.3, C-14 47.4, C-15 23.6, C-16 27.3, C-17 47.2, C-18 12.7, C-19 17.2, C-20 35.0, C-21 17.3, C-22 30.9, C-23 31.1, C-24 174.5, C-25 51.4(Ref. 0251)
Me ester m/z: 402(4%), 384(39%), 269(72%), 124(100%)(Ref. 0125)


A microbial degradation product of deoxycholic acid by Pseudomonas sp NCIB 10590.(Ref. 0125)




[0014] / [0081] / [0125] / [0251]
241
7a,12a-Dihydroxy-3-oxochol-4-en-24-oic Acid
 BBA0241
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

235-237degC(Ref. 0028)
156-157degC (Me ester)(Ref. 0001/0239)
194-195degC (Me ester)(Ref. 0255)
[a]d-22: +61deg (C=0.86, MeOH)(Ref. 0001)
[a]D: +3.0deg (C=0.23, MeOH) (Me ester)(Ref. 0255)
l max (e): 244 (18000) nm(Ref. 0028)
Me ester: lmax (EtOH) (e): 244 (14400) nm(Ref. 0255)
nmaxcm-1: 1708 (C=O), 1620 (4-ENE)(Ref. 0028)
Me ester : nmaxcm-1: 1660, 1735, 3000, 3350(a,b-unsaturater six member ketonic ring), 845, 1045, 1190, 1380, 1420-1470, 1625, 1640(Ref. 0255)
1H-NMR (CDCl3+20%DMSO-d6) d: 0.72 (3H, s, 18-CH3), 0.99 (3H, d, J=5.4Hz, 21-CH3), 1.17 (3H, s, 19-CH3), 3.93 (2H, m, 7b- and 12b-H), 5.72 (1H, s, 4-H)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.75(s), 21-Me 1.01(d), 19-Me 1.18(s), COOMe 3.70(s), 7b- and 12b-H 4.03(m), 4-H 5.88(m)(Ref. 0004/0255)
Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 35.1, C-2 33.9, C-3 198.8, C-4 126.9, C-5 167.7, C-6 40.8, C-7 68.2, C-8 40.0, C-9 38.8, C-10 38.0, C-11 28.4, C-12 72.3, C-13 46.4, C-14 42.0, C-15 23.0, C-16 27.3, C-17 47.1, C-18 12.6, C-19 16.8, C-20 35.1, C-21 17.3, C-22 30.9, C-23 31.1, C-24 174.6, C-25 51.4(Ref. 0251)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)
Me-DMES-methoxime (70eV) m/z: 619(M+), 590(M-29, 68%), 484(M-104-29), 411(M-104times2), 380(M-104times2-31, 89%), 296(M-104times2-SC, 100%)(Ref. 0204)< BR>Me ester m/z: 400(M+), 382(M-H2O), 369(M-2times19), 367(M-2H2O-15), 362(M-56), 285(M-H2O-SC), 267(M-2H2O-SC, 100%), 124(3-oxo-4-en ringA)(Ref. 0255)
Me-TMS ether m/z: 562(M+), 472(M-TMSOH), 441(M-TMSOH-31), 382(M-2TMSOH), 357(M-TMSOH-SC), 267(M-2TMSOH-SC, 100%)(Ref. 0255)
Me ester-7,12-diacetate (70eV) m/z: 502(M, 2%), 442(M-AcOH, 3%), 382(M-2AcOH, 75%), 367(16%), 351(8%), 309(5%), 267(100%), 227(13%)(Ref. 0231)


A microbiological transformation product of cholic acid by Mycobacterium mucosum 1210.(Ref. 0001)
Identified in gastric contents from neonates with high intestinal obstruction.(Ref. 0155)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Identified in amniotic fluid in early gestation.(Ref. 0192)
Major bile acid identified in urine and serum of infants with cholestasis.(Ref. 0204)
A microbiological degradation product of cholic acid by Streptomyces rubescens.(Ref. 0239)




[0001] / [0004] / [0007] / [0028] / [0155] / [0188] / [0192] / [0204] / [0231] / [0239] / [0251] / [0255]
242
7a-Hydroxy-3-oxochola-1,4-dien-24-oic Acid
 BBA0242
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

262-264degC(Ref. 0024)
lmax (EtOH) (e): 246 (14500) nm(Ref. 0120)
Me ester: lmax (EtOH) (e): 246 (14900) nm(Ref. 0120)
nmaxcm-1: 1725 (C=O), 3460 (OH), 1655, 1590 (D1.4-3-OXO)(Ref. 0024)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d : 18-Me 0.74(s), 21-Me 0.93(d), 19-Me 1.23(s), 7b-H 3.99(m), 4-H 6.07(brs), 2-H 6.17(dd, J, 9.9, 1.8), 1-H 7.11(d, J, 9.9)(Ref. 0024)
Me ester-7-acetate 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.74(s), 21-M 0.92(d), 19-Me 1.25(s), 7a-OCOMe 2.00(s), COOMe 3.66(s), 7b-H 5.05(m), 4-H 6.01(s), 2-H 6.26(dd, J, 9.9, 1.8), 1-H 7.07(d, J, 9.9)(Ref. 0121)
Me ester-7-acetate 13C-NMR(CDCl3; 125.65MHz) d: C-1 155.0, C-2 127.6, C-3 185.5, C-4 126.5, C-5 163.8, C-6 38.3, C-7 72.0, C-8 37.3, C-9 45.1, C-10 42.6, C-11 22.4, C-12 38.3 C-13 43.1, C-14 50.0, C-15 23.6, C-16 27.7, C-17 55.5, C-18 11.7, C-19 18.4, C-20 35.1, C-21 18.1, C-22 30.8, C-23 30.8, C-24 174.3, C-25 51.3(Ref. 0251)
m/z: 386(M+), 368(M-H2O), 267(M-H2O-SC), 122(100%)(Ref. 0120)
Me ester m/z: 400(M+), 382(M-H2O), 367(M-CH3-H2O), 267(M--H2O-CH3), 122(100%)(Ref. 0120)


A microbial degradation product of deoxycholic acid by Pseudomonas sp NCIB 10590.(Ref. 0125)




[0024] / [0120] / [0121] / [0125] / [0251]
243
12a-Hydroxy-3-oxochola-1,4-dien-24-oic Acid
 BBA0243
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

232-234degC, (Me ester; mp, 140-141degC)(Ref. 0120)
242-244degC (Me ester)(Ref. 0125)
lmax (EtOH) (e) : 244 (14300) nm(Ref. 0120)
Me ester : lmax (EtOH) (e) : 246 (15900) nm(Ref. 0120)
Me ester : lmax (MeOH) (loge) : 244 (4.17) nm(Ref. 0125)
Me ester: nmaxcm-1: 3450, 1734, 1660, 1618, 1602(Ref. 0125)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.78(s), 19-Me 1.04(s), 21-Me 1.28(d), COOMe 3.70(s), 12b-H 4.00(t, J, 3.0), 4-H 6.02(s), 2-H 6.15(d, J, 10.0), 1-H 6.96(s)(Ref. 0125)
Me ester-12-acetate 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.81(s), 21-M 0.81(d), 19-Me 1.21(s), 12a-OCOMe 2.03(s), COOMe 3.66(s), 12b-H 5.11(m), 4-H 6.09(s), 2-H 6.21(dd, J, 10.8, 1.8), 1-H 6.93(d, J, 10.8)(Ref. 0121)
Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 155.6, C-2 127.4, C-3 186.3, C-4 123.6, C-5 169.3, C-6 32.8, C-7 33.3, C-8 35.7, C-9 45.8, C-10 43.0, C-11 30.3, C-12 72.4, C-13 46.5, C-14 47.0, C-15 23.7, C-16 27.2, C-17 47.0, C-18 12.6, C-19 18.4, C-20 35.0, C-21 17.2, C-22 30.7, C-23 30.9, C-24 174.5, C-25 51.4(Ref. 0251)
m/z: 386(M+), 368(M-H2O), 353(M-CH3-H2O), 267(M-H2O-SC, 100%)(Ref. 0120)
Me ester m/z: 400(M+, 25%), 382(M-H2O, 27.5%), 267(M-H2O-CH3, 55%), 122(100%)(Ref. 0120/0125)


A microbial degradation product of deoxycholic acid by Pseudomonas sp NCIB 10590.(Ref. 0125)




[0120] / [0121] / [0125] / [0251]
244
7a,12a-Dihydroxy-3-oxochola-1,4-dien-24-oic Acid
 BBA0244
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

237-240degC, (Me ester; mp, 210-212degC)(Ref. 0120)
lmax (EtOH) (e): 246(15500) nm(Ref. 0120)
Me ester : lmax (EtOH) (e): 246 (16200) nm (Ref. 0120)
nmaxcm-1: 1712 (C=O), 3416 (OH), 1603 (D1.4-3-OXO)(Ref. 0024)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.74(s), 21-Me 0.99(d), 19-Me 1.21(s), 7b- and 12b-H 3.96(m), 4-H 6.07(brs), 2-H 6.18(dd, J, 9.9, 1.8), 1-H 7.09(d, J, 9.9)(Ref. 0024)
Me ester-7,12-diacetate 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.81(s), 21-M 0.81(d), 19-Me 1.23(s), 7a- and 12a-OCOMe 2.04 and 2.07(s), COOMe 3.66(s), 7b- and 12b-H 5.09(m), 4-H 6.03(s), 2-H 6.25(dd, J, 9.9, 1.8), 1-H 6.95(d, J, 9.9)(Ref. 0121)
Me ester-7,12-diacetate 13C-NMR(CDCl3; 125.65MHz) d: C-1 154.1, C-2 128.0, C-3 185.4, C-4 126.8, C-5 163.0, C-6 37.3, C-7 71.5, C-8 38.3, C-9 40.0, C-10 42.5, C-11 26.9, C-12 74.5, C-13 45.1, C-14 43.1, C-15 22.9, C-16 26.9, C-17 47.3, C-18 12.2, C-19 18.2, C-20 34.5, C-21 17.4, C-22 30.6, C-23 30.8, C-24 174.2, C-25 51.4(Ref. 0251)
m/z: 384(M-H2O), 366(M-2H2O), 265(M-2H2O-SC, 100%)(Ref. 0120)
Me ester m/z: 416(M+), 398(M-H2O), 380(M-2H2O), 283(M-H2O-SC), 265(M-2H2O-SC), 122(100%)(Ref. 0120)







[0024] / [0120] / [0121] / [0251]
245
12a-Hydroxy-3-oxochola-4,6-dien-24-oic Acid
 BBA0245
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

264-266degC(Ref. 0081)
144-146degC (Me ester)(Ref. 0001/0252)
l max (e): 284 (30000) nm(Ref. 0081)
nmaxcm-1: 1718, 1708 (C=O, acid), 1648(C=O, 4,6-diene-3-keto), 1616, 1584(C=C)(Ref. 0081)
Me ester: nmaxcm-1: 1578, 1612(4,6-diene), 1664(3-ketone), 1719(carboxy), 3505(hydroxy)(Ref. 0252)
1H-NMR (CDCl3; 100MHz) d: 18-Me 0.74(s), 21-Me 0.98(d), 19-Me 1.08(s), 12b-H 3.96(brs), 4-H 5.56(s), 6- and 7-H 6.10(s)(Ref. 0081)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.774(s), 21-Me 0.993(d), 19-M 1.092(s), COOMe 3.661(s), 12b-H 4.059(brs), 4-H 5.656(s), 7-H 6.089(dd, J, 9.5, 2.0), 6-H 6.143(d, J, 9.5)(Ref. 0071/0252)
Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 33.5, C-2 33.7, C-3 199.3, C-4 123.3, C-5 163.7, C-6 127.7, C-7 141.0, C-8 37.7, C-9 43.5, C-10 35.4, C-11 28.3, C-12 72.0, C-13 47.1, C-14 45.1, C-15 23.0, C-16 27.1, C-17 46.9, C-18 12.2, C-19 15.9, C-20 35.0, C-21 17.1, C-22 30.7, C-23 30.9, C-24 174.4, C-25 51.3(Ref. 0251)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)
Me-DMES-methoxime (70eV) m/z: 515(M+, 5%), 411(M-104, 59%), 296(M-104-SC, 100%)(Ref. 0204)
Me ester m/z: 400(M, 6%), 382(M-H2O, 34%), 267(M-SC-H2O, 100%), 136(4.6-dien-3-one, 11%)(Ref. 0252)
Me ester-12-acetate (70eV) m/z: 442(M, 1%), 382(M-AcOH, 64%), 367(19%), 295(6%), 267(100%), 225(24%)(Ref. 0231)


Semisynthetic steroid produced from various substrates by incubating with Corynebacterium simplex.(Ref. 0001)
A major bile acid identified in urine and serum of infants with cholestasis.(Ref. 0204)
A bacterial degradation product of cholic acid by Pseudomonas sp. N.C.I.B. 10590.(Ref. 0252)




[0001] / [0007] / [0071] / [0081] / [0204] / [0231] / [0251] / [0252]
246
1b,3a,7b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0246
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file


Me-TMS ether m/z: 623, 549, 548, 459, 458, 396, 368, 218, 217, 195, 143(Ref. 0124)


Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in serum, faeces, liver tissue and urine from patients with primary biliary cirrhosis.(Ref. 0149/0176/0200)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)




[0124] / [0149] / [0176] / [0188] / [0200]
247
3a,5b,7b-Trihydroxycholan-24-oic Acid
 BBA0247
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

148-149degC (Me ester-3,7-diacetate)(Ref. 0228)
Me ester-3,7-diacetate: nmaxcm-1: 1027, 1366, 1729, 2874, 2910, 2935, 3600(Ref. 0228)
Me ester-3,7-diacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.68(s), 21-Me 0.92(d), 19-Me 0.94(s), 3a- and 7b-OCOMe 1.99 and 2.02(each s), 23-H 2.23(m), 23'-H 2.35(m), COOMe 3.67(s), 7a-H 4.64(td, J, 11.0, 5.5), 3b-H 5.06(m)(Ref. 0228)
Me ester-3,7-diacetate 13C-NMR (CDCl3; 125MHz) d: C-1 29.0, C-2 25.8, C-3 70.6, C-4 39.0, C-5 74.4, C-6 41.9, C-7 73.9, C-8 39.2, C-9 41.3, C-10 39.0, C-11 21.2, C-12 39.6, C-13 43.3, C-14 55.3, C-15 25.5, C-16 28.3, C-17 54.9, C-18 11.9, C-19 16.1, C-20 35.1, C-21 18.2, C-22 30.9, C-23 30.8, C-24 174.8, C-25 51.4(Ref. 0228)
Me-TMS ether m/z: 638(M+), 623(M-15), 548(M-TMSOH), 533(M-15-TMSOH), 458(M-2TMSOH), 443(M-15-2TMSOH), 368(M-3TMSOH), 353(M-15-3TMSOH), 343(ABCD-skeleton+TMSOH), 253(ABCD-skeleton), 493, 403, 331, 289, 229(Ref. 0124/0188)
Me ester-3,7-diacetate m/z: 428(5%), 386(53%), 368(63%), 353(16%), 332(100%), 331(17%), 313(27%), 271(78%), 253(63%), 226(10%), 211(16%)(Ref. 0228)


Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
A biotransformation product of ursodeoxycholic acid in the isolated perfused rat liver.(Ref. 0183)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)




[0124] / [0183] / [0188] / [0228]
248
3a,7b,21x-Trihydroxy-5b-cholan-24-oic Acid
 BBA0248
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file


Me-TMS ether m/z: 638(M+), 623(M-15), 548(M-TMSOH), 535, 533(M-15-TMSOH), 458(M-2TMSOH), 445, 443(M-15-2TMSOH), 368(M-3TMSOH), 355, 353(M-15-3TMSOH), 255(ABCD-skeleton), 509(M-129), 419(M-129-TMSOH),329(M-129-2TMSOH), 391(M-157-TMSOH), 301(M-157-2TMSOH)(Ref. 0124)


Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in serum and urine of patients with primary biliary cirrhosis.(Ref. 0149)




[0124] / [0149]
249
3a,7b,22x-Trihydroxy-5b-cholan-24-oic Acid
 BBA0249
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file


Me-TMS ether m/z: 623(M-15), 548(M-TMSOH), 458(M-2TMSOH), 443(M-15-2TMSOH), 368(M-3TMSOH), 353(M-15-3TMSOH), 464(M-175), 374(M-175-TMSOH), 284(M-175-2TMSOH), 175(C-22+C-23+C24)(Ref. 0124)


Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in serum and urine of patients with intrahepatic cholestasis of pregnancy.(Ref. 0188)
Stereochemistry of a hydroxyl group at C-22 is unidentified(Ref. 0124)



[0124] / [0188]
250
(23R)-3a,7b,23-Trihydroxy-5b-cholan-24-oic Acid
 BBA0250
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file


Me-TMS ether (70eV) m/z: 623, 548, 489, 458, 399, 368, 309, 297, 255, 234, 201, 162, 159, 129(Ref. 0127)


Occurred in human urine of patients suffering cerebrotendinous xanthomatosis.(Ref. 0127)




[0127]
251
(23S)-3a,7b,23-Trihydroxy-5b-cholan-24-oic Acid
 BBA0251
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file


Me-TMS ether (70eV) m/z: 623, 548, 489, 458, 399, 368, 309, 297, 234, 163, 162, 159(Ref. 0127)


Occurred in human urine of patients suffering cerebrotendinous xanthomatosis.(Ref. 0127)




[0127]
252
2x,3a,6a,7a-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0252
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file


Me-TMS ether (22.5eV) m/z: 726(M+), 639(M-TMSOH), 546(M-2TMSOH), 456(M-3TMSOH), 367(M-4TMSOH), 431, 341, 251, 314, 224, 217, 143, 142, 129, 271, 181, 507, 417, 327(Ref. 0126)


Isolated from urine of healthy infants, born after 35-39 weeks of gestation. ; stereochemistry of a hydroxyl group at C-2 is unidentified.(Ref. 0126)




[0126]
253
3a-Hydroxy-11-oxo-5b-chol-8-en-24-oic Acid
 BBA0253
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

128.7-129.9degC (Me ester-3-acetate)(Ref. 0055)
[a]d-24 : +144.4pm1deg (1.62% ,CHCl3) (Me ester-3-acetate)(Ref. 0055)
Me ester-3-acetate: lmax (EtOH) (loge): 254(3.94) nm(Ref. 0055)
Me ester-3-acetate: nmaxmCHCl3: 5.74, 5.98, 6.21<0055>>









[0055]
254
(23R)-3a,7a,12a,23-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0254
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

194-196degC (Me ester)(Ref. 0052)
[a]d-23: +31deg (C=1.0) (Me ester)(Ref. 0052)
M/D: +136 (Me ester)(Ref. 0052)

Me-TMS ether (70eV) m/z: 711, 547, 546, 457, 456, 429, 355, 343, 282, 254, 253, 221, 171, 147, 143, 129(Ref. 0127)


Isolated from seal and snakes bile.(Ref. 0001/0101)
Isolated from Baltic seal ; the stereochemistry of a hydroxyl group at C-23 is unidentified.(Ref. 0100)
Isolated from snake bile ; identified in Gaboon viper BItis gabonica and Puff adder B. arietans ; stereochemistry of a hydroxyl group at C-23 is unidentified.(Ref. 0100)
A primary bile acid in marine manmals and snakes.(Ref. 0102)
Occurred in human urine of patients suffering cerebrotendinous xanthomatosis.(Ref. 0127)Identified in urine of healthy humans and patients with liver diseases. : stereochemistry of a hydroxyl group at C-23 is unidentified.(Ref. 0150/0151)
Isolated from the leopard seal, Hydrurga leptonyx, and the Californian sealion, Zalophus californianus.(Ref. 0168)
Isolated from snakes of the subfamily Viperinae ; a biotransformation product of cholic acid in the adder (Vipera berus ; linn.) liver. ; stereochemistry of a hydroxyl groups at C-23 is unidentified.(Ref. 0175)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)




[0001] / [0052] / [0100] / [0101] / [0102] / [0127] / [0150] / [0151] / [0168] / [0175] / [0206]
255
3a,19-Dihydroxy-5b-cholan-24-oic Acid
 BBA0255
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

220-222degC(Ref. 0128)
[a]d-23: +35.8deg (C=0.62, MeOH)(Ref. 0128)
lmaxcm-1: 3350, 2700, 1710(Ref. 0128)
1H-NMR (Pyridine-d5; 400MHz) d: 18-Me 0.62(s), 19-H2 3.72 and 4.12(d, J=9Hz), 21-Me 0.96(d, J=6Hz), 3b-H 4.00(m)(Ref. 0128)
Me-DMES ether (70eV) m/z: 461(M-117), 357(M-DMESOH-117), 371(M-DMESOH-DMESO), 255(M-2DMESOH-SC), 549(M-C2H5)(Ref. 0128)







[0128]
256
3a,7a,19-Trihydroxy-5b-cholan-24-oic Acid
 BBA0256
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

129-130degC(Ref. 0128)
[a]d-23: +21.1deg (C=0.59, MeOH)(Ref. 0128)
lmaxcm-1: 3350, 2650, 1700(Ref. 0128)
1H-NMR (Pyridine-d5; 400MHz) d: 18-Me 0.72(s), 19-H2 3.88 and 4.23(d, J=11Hz), 21-Me 1.04(d, J=6Hz), 3b-H 3.94(m), 7b-H 4.07(brs)(Ref. 0128)
Me-DMES ether (70eV) m/z: 459(M-DMESOH-117), 355(M-2DMESOH-117), 472(M-2DMESOH), 369(M-2DMESOH-DMESO), 253(M-3DMESOH-SC)(Ref. 0128)







[0128]
257
3a,12a,19-Trihydroxy-5b-cholan-24-oic Acid
 BBA0257
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

138-140degC(Ref. 0128)
[a]d-23: +58.5deg (C=1.36, MeOH)(Ref. 0128)
nmaxcm-1: 3350, 2650, 1690(Ref. 0128)
1H-NMR (Pyridine-d5; 400MHz) d: 18-Me 0.73(s), 19-H2 3.57 and 3.82(d, J=10Hz), 21-Me 1.16(d, J=6Hz), 3b-H 3.90(m), 12b-H 4.16(brs)(Ref. 0128)
Me-DMES ether (70eV) m/z: 459(M-DMESOH-117), 355(M-2DMESOH-117), 472(M-2DMESOH), 369(M-2DMESOH-DMESO), 253(M-3DMESOH-SC)(Ref. 0128)







[0128]
258
1a-Hydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0258
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

136-137degC (Me ester)(Ref. 0044)
[a]D: +11deg (CHCl3)(Ref. 0044)
Me ester: nmaxcm-1: 1730 (C=O), 3500 (OH)(Ref. 0044)
Me ester 1H-NMR (CDCl3) d: 1b-H 3.42, COOMe 3.6(Ref. 0044)








[0044]
259
1,3,7-Trioxo-5b-cholan-24-oic Acid
 BBA0259
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

Me ester 1H-NMR (CDCl3+aceton-d6; 300MHz) d: 18-Me 0.69(s), 21-Me 0.93(d), 19-Me 1.38(s), 2.43(bt), 2.84(b), COOMe 3.62(s), 2-H 5.01(bs)(Ref. 0039)








[0039]
260
3,12,15-Trioxo-5b-cholan-24-oic Acid
 BBA0260
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

176-177degC (Me ester)(Ref. 0057/0058)
nmaxcm-1: 1712, 1739 (Me ester)(Ref. 0057)
Me ester: nmax(CDCl3)cm-1: 1739-1710(Ref. 0058)

Me ester m/z: 416(M+), 301(M-SC), 247(100%), 211(ring D (42)+SC+H)(Ref. 0057/0058)







[0057] / [0058]
261
(23S)-3a,7a,12a,23-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0261
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

195-197degC (Me ester)(Ref. 0052)
[a]d-23: +41deg (C=0.5, MeOH) (Me ester)(Ref. 0052)
M/D: +180 (Me ester)(Ref. 0052)









[0052]
262
3a,7b,12a-Trihydroxy-6-oxo-5a-cholan-24-oic Acid
 BBA0262
Takashi Iida
C24H38O6 422.555 Download ChemDraw structure file

219-221degC, (Me ester; mp, 162-163.5degC)(Ref. 0037/0237)
[a]d-21: +50pm2deg (C=1.5, EtOH)(Ref. 0085/0237)
nmaxcm-1: 1713, 1687 (C=O), 3528, 1039, 1014, 990 (OH)(Ref. 0037)
1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18- and 19-Me 0.67(s), 21-Me 1.00(s), 7a-H 3.80(d, J,9.0), 12b-H 3.95(m), 3b-H 4.05(m)(Ref. 0037)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 19-Me 0.71(s), 21-Me 0.99(d), COOMe 3.67(s), 7a-H 3.85(d, J,9.0), 12b-H 4.04(m), 3b-H 4.18(m)(Ref. 0037)








[0037] / [0085] / [0237]
263
5b-Chol-3-en-24-oic Acid
 BBA0263
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

144-145degC, (Me ester; mp, 74.5-75.5degC)(Ref. 0130)
[a]d-20: +21.5deg (C=0.506, CHCl3)(Ref. 0130)
[a]D: +17.8deg (CHCl3) (Me ester)(Ref. 0105)
nmaxcm-1: 1730 (COOH), 3050, 1620 (CH=CH)(Ref. 0130)
1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.95(s), 4-H 5.30(d, J, 11.0), 3-H 5.65(dd, J, 10.0, 4.0)(Ref. 0130)
Me ester 1H-NMR(CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.96(s), COOMe 3.66(s), 4-H 5.36(d, J, 10.0), 3-H 5.70(dd, J, 10.0, 4.0)(Ref. 0130/0225)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 34.1, C-2 23.0, C-3 127.0, C-4 132.3, C-5 43.5, C-6 25.7, C-7 27.5, C-8 35.7, C-9 40.9, C-10 34.1, C-11 21.5, C-12 40.3, C-13 42.8, C-14 56.3, C-15 24.3, C-16 28.2, C-17 56.0, C-18 12.0, C-19 22.4, C-20 35.4, C-21 18.3, C-22 31.1, C-23 31.1, C-24 174.7, C-25 51.4(Ref. 0244)
Me ester (70eV) m/z: 372(M+, 100%), 355(M-CH3, 23%), 257(M-SC, 19%), 230(16%), 215(58%)(Ref. 0105/0130)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)







[0007] / [0105] / [0130] / [0225] / [0244]
264
Chol-4-en-24-oic Acid
 BBA0264
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

160degC(Ref. 0001)
92-93degC (Me ester)(Ref. 0129)
[a]D: +70deg (C=1.2, CHCl3) (Me ester)(Ref. 0129)
nmaxcm-1: 810(Ref. 0129)









[0001] / [0129]
265
Chol-5-en-24-oic Acid
 BBA0265
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

160-161degC, (Me ester; mp, 78-80degC)(Ref. 0001)
[a]D: -67deg (CHCl3), [a]D: -43deg (CHCl3) (Me ester)(Ref. 0001)
Me ester 1H-NMR(CDCl3) d: 18-Me 0.68(s), 21-Me 0.91(d), 19-Me 1.01(s), COOMe 3.66(s), 4-H 5.31-5.28(m)(Ref. 0225)








[0001] / [0225]
266
5b-Chol-6-en-24-oic Acid
 BBA0266
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

162-163degC, (Me ester; mp, 61-62degC)(Ref. 0132)
[a]d-20: -6pm2deg (C=2.0), [a]d-20: -8pm2deg (C=2.0) (Me ester)(Ref. 0132)









[0132]
267
5b-Chol-7-en-24-oic Acid
 BBA0267
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

150-151degC, (Me ester; mp, 98-99degC)(Ref. 0072)
[a]d-23: +53pm3deg (CHCl3) (Me ester)(Ref. 0072)









[0072]
268
5b-Chol-8-en-24-oic Acid
 BBA0268
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

132-133degC(Ref. 0133)
[a]d-19: +38.1deg (C=0.64, CHCl3)(Ref. 0133)









[0133]
269
5b-Chol-8(14)-en-24-oic Acid
 BBA0269
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

142-143.5degC(Ref. 0133)
[a]37D: +39.1deg (C=0.77, CHCl3)(Ref. 0133)









[0133]
270
7-Oxo-5a-cholan-24-oic Acid
 BBA0270
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

82-84degC (Me ester)(Ref. 0041)
[a]d-25: -41.6pm0.5deg (C=1%, MeOH)(Ref. 0041)
nmaxcm-1: 1739 (COOMe), 1712 (C=O), 1171 (COOMe)(Ref. 0041)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.92(s), 21-Me 1.04(d)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 38.2, C-2 21.7, C-3 26.4, C-4 29.0, C-5 49.1, C-6 46.5, C-7 212.1, C-8 50.1, C-9 54.7, C-10 36.6, C-11 21.1, C-12 38.7, C-13 42.5, C-14 48.9, C-15 24.9, C-16 28.2, C-17 56.1, C-18 12.0, C-19 11.6, C-20 35.2, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.5, C-25 51.3(Ref. 0065)








[0008] / [0041] / [0065]
271
6b,12a-Dihydroxy-3-oxochol-4-en-24-oic Acid
 BBA0271
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

184-186degC (Me ester )(Ref. 0030)
Me ester : nmaxcm-1: 1734, 1691 (C=O), 1615 (C=C), 3500, 1039, 980 (OH)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.77(s), 21-Me 0.98(d), 19-Me 1.36(s), COOMe 3.66(s), 12b-H 4.06(m), 6a-H 4.34(m), 4-H 5.80(brs)(Ref. 0030/0071)








[0030] / [0071]
272
6b,12a-Dihydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0272
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

138-139degC (Me ester )(Ref. 0030)
Me ester : nmaxcm-1: 1721 (C=O), 3555, 3373, 1028, 974 (OH)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.75(s), 19-Me 1.20(s), 21-Me 0.98(d), COOMe 3.66(s), 6a-H 3.71(m), 12b-H 4.06(m)(Ref. 0030)








[0030]
273
6a,12a-Dihydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0273
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

153-155degC (Me ester )(Ref. 0030)
Me ester : nmaxcm-1: 1732, 1708 (C=O), 3450, 1045, 1015 (OH)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.99(s), COOMe 3.66(s), 12b-H 4.04(m), 6b-H 4.16(brm)(Ref. 0030)








[0030]
274
3a,6a,12a-Trihydroxy-7-oxo-5b-cholan-24-oic Acid
 BBA0274
Takashi Iida
C24H38O6 422.555 Download ChemDraw structure file

Me ester: nmaxcm-1: 1716 (C=O), 3466 (OH)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.69(s), 21-Me 0.98(d), 19-Me 1.22(s), 3b-H 3.57(brm), COOMe 3.67(s),12b-H 4.01(m), 6b-H 4.51(m)(Ref. 0034)








[0034]
275
3-Oxo-5b-chol-1-en-24-oic Acid
 BBA0275
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

137-139degC (Me ester )(Ref. 0093)
[a]D: +120deg (CHCl3 ) (Me ester)(Ref. 0044)
Me ester: lmax (MeOH) (e): 233(8500) nm(Ref. 0093)
Me ester: nmaxcm-1: 3030, 1745, 1690, 1615(Ref. 0093)
Me ester 1H-NMR(CDCl3; 200MHz) d: 18-Me 0.70(s), 21-Me 0.92(d), 19-Me 1.20(s), COOMe 3.65(s),2-H 5.85(d, J, 10.0), 1-H 6.80(d, J, 10.0)(Ref. 0093)
Me ester 13C-NMR(CDCl3; 50MHz) d: C-1 161.4, C-2 126.9, C-3 200.4, C-4 38.5, C-5 46.2, C-6 26.4, C-7 25.9, C-8 35.2, C-9 40.9, C-10 39.0, C-11 22.3, C-12 39.8, C-13 42.6, C-14 55.7, C-15 24.1, C-16 27.9, C-17 55.9, C-18 12.0, C-19 20.8, C-20 35.2, C-21 30.9, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.3(Ref. 0093)
Me ester m/z: 380(M+, 16%), 271(14%), 244(3%), 134(31%), 122(100%), 109(69%)(Ref. 0093)







[0044] / [0093]
276
3a-Hydroxy-1,7-dioxo-5b-cholan-24-oic Acid
 BBA0276
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

Me ester 1H-NMR(CDCl3; 300MHz) d: 18-Me 0.65(s), 21-Me 0.89(d), 19-Me 1.38(s), 23-H 2,2-2.4(m), 8b-H 2.51(t, J, 12.0), 5b-H 2.64(m), 6b-H 2.86(dd, J, 13.2, 5.7), COOMe 3.66(s), 3b-H 3.85(br)(Ref. 0039)
Me ester (22eV) m/z: 418(M+, 89%), 400(M-H2O, 29%), 369(M-H2O-CH3O, 16%), 345(M-CH2COOCH3, 42%), 303(M-SC, 59%), 292(CD-ring ion, 39%), 285(M-H2O-SC, 43%), 208(AB-ring ion, 100%), 108(A-ring ion-H2O, 20%)(Ref. 0039)







[0039]
277
1,7-Dioxo-5b-chol-2-en-24-oic Acid
 BBA0277
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file


Me ester (22eV) m/z: 368(M-CH3OH, 0.5%), 351(M-H2O-CH3O, 1.5%), 350(M-H2O-CH3OH, 0.5%), 327(M-CH2COOCH3, 3%), 292(CD-ring ion, 2.5%), 285(M-SC, 48%), 267(M-H2O-SC, 12%), 190(11%), 177(CD-ring ion-SC, 6%),159(CD-ring ion-SC-H2O, 4%), 115(SC, 3%), 108(A-ring ion, 100%), 68(RDA ion, 4%)(Ref. 0039)







[0039]
278
7a-Hydroxy-5b-chol-2-en-24-oic Acid
 BBA0278
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file


Me ester-7-acetate (70eV) m/z: 430(M+, 0%), 370(M-AcOH, 75%), 355(M-AcOH-CH3, 19%), 339(11%), 316(M-AcOH-54, 100%), 255(M-AcOH-SC, 25%), 249(rings C and D+SC, 5%), 208(26%), 201(M-AcOH-SC-54, 36%)(Ref. 0105)







[0105]
279
3a,7a-Dihydroxychol-5-en-24-oic Acid
 BBA0279
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

208-209degC, (Me ester; mp, 165-170degC)(Ref. 0114)
[a]d-25: -139.2deg (dioxane)(Ref. 0114)









[0114]
280
3a,7b-Dihydroxychol-5-en-24-oic Acid
 BBA0280
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

200-203degC, (Me ester; mp, 167-170degC)(Ref. 0114)
[a]d-24: +26.3deg (dioxane)(Ref. 0114)









[0114]
281
3,12-Dioxochola-1,4-dien-24-oic Acid
 BBA0281
Takashi Iida
C24H32O4 384.508 Download ChemDraw structure file

153-156degC(Ref. 0131)
208-210degC (Me ester)(Ref. 0125)
Me ester: lmax (e), (loge): 244.0 (10400), (4.15) nm(Ref. 0121/0125)
Me ester: nmaxcm-1: 1704, 1735 (C=O), 1600, 1622, 1660 (D1.4-3-OXO)(Ref. 0121/0125)
Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.86(d), 18-Me 1.11(s), 19-Me 1.31(s), COOMe 3.66(s), 4-H 6.10(s), 2-H 6.25(dd, J, 9.9, 1.8), 1-H 6.87(d, J, 9.9)(Ref. 0121)
Me ester m/z: 398(12%), 283(14%), 121(100%)(Ref. 0125)


A microbial degradation product of deoxycholic acid by Pseudomonas sp NCIB 10590.(Ref. 0125)




[0121] / [0125] / [0131]
282
7b-Hydroxy-3-oxochola-1,4-dien-24-oic Acid
 BBA0282
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

140-141degC (Me ester-7-acetate)(Ref. 0121)
Me ester-7-acetate: lmax (e): 243.6 (14300) nm(Ref. 0121)
Me ester-7-acetate: nmaxcm-1: 1722 (C=O), 1601, 11626, 1660 (D1.4-3-OXO), 1022, 1164, 1242 (acetate)(Ref. 0121)
Me ester-7-acetate 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.76(s), 21-Me 0.92(d), 19-Me 1.28(s), 7b-OCOMe 2.04(s), COOMe 3.66(s), 7a-H 4.59(brm), 4-H 6.12(s), 2-H 6.24(dd, J, 10.8, 1.8), 1-H 7.04(d, J, 9.9)(Ref. 0121)
Me ester-7-acetate 13C-NMR(CDCl3; 125.65MHz) d: C-1 154.6, C-2 127.8, C-3 185.5, C-4 125.5, C-5 162.9, C-6 25.4, C-7 76.2, C-8 38.1, C-9 48.7, C-10 42.6, C-11 21.4, C-12 39.2, C-13 43.4, C-14 54.5, C-15 23.1, C-16 28.1, C-17 54.8, C-18 12.0, C-19 18.7, C-20 35.0, C-21 18.2, C-22 30.8, C-23 30.9, C-24 174.3, C-25 51.3(Ref. 0251)








[0121] / [0251]
283
6a-Hydroxy-3-oxochola-1,4-dien-24-oic Acid
 BBA0283
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

Me ester-6-acetate: lmax (e): 244.4 (15000) nm(Ref. 0121)
Me ester-6-acetate: nmaxcm-1: 1740 (C=O), 1608, 1627, 1670, (D1.4-3-OXO), 1050, 1185, 1250 (acetate)(Ref. 0121)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.72(s), 21-Me 0.90(d), 19-Me 1.20(s), COOMe 3.66(s), 6b-H 4.46(m), 2-H 6.23(s), 4-H 6.46(s), 1-H 6.98(d, J, 10.0)(Ref. 0004)
Me ester-6-acetate 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.74(s), 21-Me 0.92(d), 19-Me 1.28(s), 6a-OCOMe 2.15(s), COOMe 3.66(s), 6b-H 5.55(brm), 4-H 6.25(s), 2-H 6.25(dd, J, 10.8, 1.8), 1-H 7.03(d, J, 10.8)(Ref. 0121)








[0004] / [0121]
284
3a,7a-Dihydroxy-5b-chol-11-en-24-oic Acid
 BBA0284
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

206-209degC, (Me ester-3-acetate; mp, 138-140degC)(Ref. 0134)
137-139degC (Me ester-3,7-diacetate)(Ref. 0105/0227/0254)
[a]d-25: +6.9deg (C=3.19, CHCl3) (Me ester-3,7-diacetate)(Ref. 0105/0227)
Me ester-3-acetate 1H-NMR (CDCl3; 100MHz) d: 5.45(dd, J, 10.0, 1.5), 6.15(dd, J, 10.0, 3.0)(Ref. 0134)
Me ester-3,7-diacetate 1H-NMR (CDCl3; 100MHz) d: 3a- and 7a-OCOMe 2,00 2.04(s), COOMe 3.65(s), 3b-H 4.58(m), 7b-H 5.00(m), 11- and 12-H 5.44, 6.15(q)(Ref. 0105/0254)
Me ester-3-acetate (70eV) m/z: 368(M-2AcOH), 353(M-2AcOH-CH3), 253(M-2AcOH-SC)(Ref. 0134)
Me ester-3,7-acetate m/z: 488(M+, 0%), 428(M-AcOH, 34%), 413(M-AcOH-CH3, 12%), 368(M-2AcOH, 76%), 353(M-2AcOH-CH3, 50%), 314(M-2AcOH-54, 24%), 313(M-AcOH-SC, 16%), 286(12%), 253(M-2AcOH-SC, 98%), 211(39%), 199(M-2AcOH-SC-54, 29%)(Ref. 0105)
CI mass spectrum; Me ester-3-acetate m/z: 498(MH+), 429(MH+-AcOH), 369(MH+-2AcOH)(Ref. 0134)







[0105] / [0134] / [0227] / [0254]
285
(23S)-3a,12a,23-Trihydroxy-5b-cholan-24-oic Acid
 BBA0285
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

225degC, (Me ester; mp, 143-144degC)(Ref. 0053)
[a]d-20: +38deg (C=1.8, EtOH), [a]d-20: +56.7deg (C=1.8, EtOH) (Me ester)(Ref. 0053)
Me ester: nmaxcm-1: 1730 (C=O), 3500 (OH)(Ref. 0053)
Me ester 1H-NMR (CDCl3+CD3OD) d: 18-Me 0.69(s), 19-Me 0.91(s), 21-Me 1.07(d), 3b-H and 3timesOH 3.17(m), COOMe 3.97(s), 12b-H 4.01(m), 23-H 4.26(m)(Ref. 0053)
Me ester 13C-NMR d: C20 34.39, C21 18.26, C22 41.29, C23 70.14, C24 172.20, C25 52.15(Ref. 0053)








[0053]
286
3b-Hydroxy-5b-chol-1-en-24-oic Acid
 BBA0286
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

169-170.5degC(Ref. 0090)
[a]D: +135deg (C=0.8, dioxane5)(Ref. 0090)









[0090]
287
(22E)-3b-Hydroxy-5a-chola-7,22-dien-24-oic Acid
 BBA0287
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

131degC (Me ester-3-acetate)(Ref. 0098)
[a]d-20: +44deg (C=3.58, CHCl3) (Me ester-3-acetate)(Ref. 0098)
Me ester-3-acetate 1H-NMR (CDCl3; 60MHz) d: COOMe 5.73(s), 23-H 5.76(d, J, 15.0), 22-H 6.89(dd, J, 15.0, 9.0)(Ref. 0098)








[0098]
288
3a,11b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0288
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

201degC(Ref. 0135)
146-149degC (Me ester-3-acetate)(Ref. 0055)
[a]D: +55deg(Ref. 0001/0135)
[a]d-22: +59.0pm0.8deg (1.392%, acetone) (Me ester-3-acetate)(Ref. 0055)









[0001] / [0055] / [0135]
289
11-Oxo-5b-cholan-24-oic Acid
 BBA0289
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

89.4-90.5degC (Me ester)(Ref. 0055)
[a]d-20: +48.1pm2deg (2.10%, acetone)(Ref. 0055)









[0055]
290
3,11-Dioxo-5b-cholan-24-oic Acid
 BBA0290
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

176.2-178.2degC(Ref. 0055)
[a]d-29: +62pm2deg (2.16%, acetone)(Ref. 0055)









[0055]
291
3a,9a-Dihydroxy-11-oxo-5b-cholan-24-oic Acid
 BBA0291
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

149.0-150.4degC (Me ester-3-acetate)(Ref. 0055)
[a]d-22: +83.4pm2deg (1.32%, CHCl3) (Me ester-3-acetate)(Ref. 0055)
Me ester-3-acetate: nmax(CS2) mm: 2.75(OH), 5.75(acetate), 5.77(COOMe), 5.85(11-oxo), 8.08(acetyl group)(Ref. 0055)









[0055]
292
3b,9a-Dihydroxy-11-oxo-5b-cholan-24-oic Acid
 BBA0292
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

143.8-144.6degC (Me ester-3-acetate)(Ref. 0055)
[a]d-21: +58.2pm2deg (1.22%, CHCl3) (Me ester-3-acetate)(Ref. 0055)
Me ester-3-acetate: nmax(CHCl3) mm: 2.87, 5.89-5.94(Ref. 0055)









[0055]
293
3-Oxo-5b-chol-9(11)-en-24-oic Acid
 BBA0293
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

117-119degC (Me ester)(Ref. 0110)
[a]d-22: +35pm1deg (CHCl3) (Me ester)(Ref. 0110)
Me ester: lmax(CHCl3) mm: 5.79, 5.83(Ref. 0110)









[0110]
294
2b,3a,7a,12a-Tetrahydroxy-5a-cholan-24-oic Acid
 BBA0294
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

250-252degC(Ref. 0218)
[a]d-25: +26.5pm1.6deg (C=0.15, EtOH)(Ref. 0218)
1H-NMR (C5D5N) d: 18-Me 0.79(s), 21-Me 1.20(d), 19-Me 1.40(s), 2a- and 3b-H 4.27(nm, w1/2, 6.0), 7b-H 4.09(m), 12b-H 4.16(m)(Ref. 0218)
Me ester 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.68, 19-Me 0.92(s), 21-Me 0.97(d), 2a,3b and 7b-H 4.91(m), 12b-H 3.96(t)(Ref. 0218)
Me ester-2,3,7,12-tetraacetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.71, 19-Me 0.90(s), 21-Me 0.79(d), 2b,3a and 7a-OCOMe 2.01, 2.06, 2.09(each s), 2a,3b and 7b-H 4.89(m), 12b-H 5.03(t, J, 6.0)(Ref. 0218)
(70eV) m/z: 406(M-H20), 388(M-2H20), 370(M-3H20), 305(M-H20-SC), 287(M-2H20-SC), 269(M-3H20-SC), 251(M-4H20-SC)(Ref. 0218)







[0218]
295
3,12-Dioxo-5b-chol-14-en-24-oic Acid
 BBA0295
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

134degC (Me ester)(Ref. 0072/0104)
[a]d-22: +60deg (CHCl3) (Me ester)(Ref. 0072/0104)
Me ester: lmax (EtOH) (e): 210 (2140) nm(Ref. 0104)
Me ester: nmaxcm-1: 1738, 1705 (C=O), 780 (=C-H)(Ref. 0104)









[0072] / [0104]
296
3-Oxo-5b-chol-14-en-24-oic Acid
 BBA0296
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

89-90degC (Me ester)(Ref. 0072/0104)
[a]d-24: +38.8deg (CHCl3) (Me ester)(Ref. 0072/0104)
Me ester: lmax (EtOH) (e): 210 (1990) nm(Ref. 0104)
Me ester: nmaxcm-1: 1742, 1715 (C=O), 777 (=C-H)(Ref. 0104)









[0072] / [0104]
297
3-Oxo-5b-chol-7-en-24-oic Acid
 BBA0297
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

125degC (Me ester)(Ref. 0072)
[a]d-23: +53.3deg (CHCl3) (Me ester)(Ref. 0072/0104)
Me ester: lmax (EtOH) (e): 212 (2320) nm(Ref. 0104)
Me ester: nmaxcm-1: 1740, 1712 (C=O), 795 (=C-H)(Ref. 0104)









[0072] / [0104]
298
3a,7b-Dihydroxy-5b-chol-11-en-24-oic Acid
 BBA0298
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

[a]d-21: +36.9deg (C=0.623, dioxane) (Me ester-3,7-dioxane)(Ref. 0130)
Me ester-3,7-diacetate: nmaxcm-1: 1740 (COOMe, OCOMe), 3040 (CH=CH)(Ref. 0130)
Me ester-3,7-diacetate 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.73(s), 19-Me 0.93(s), 3- and 7-OCOMe 2.00(s), COOMe 3.68(s), 12-H 5.29(d, J, 12.0), 11-H 6.07(dd, J, 12.0, 5.0)(Ref. 0130)








[0130]
299
3a-Hydroxy-5b-chola-8,14-dien-24-oic Acid
 BBA0299
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

132-133degC, (Me ester-3-acetate; mp, 113-114degC)(Ref. 0133)
[a]d-24: -17.4deg (C=1.14, CHCl3)(Ref. 0133)
lmax (EtOH) (e): 248 (16180) nm(Ref. 0133)









[0133]
300
3a,12a,15b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0300
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.94(s), 19-Me 0.94(s), 15a-H 4.18(t, J, 7.5)(Ref. 0004/0136)
Me-TMS ether m/z: 623(M-CH3), 458(M-2TMSOH, 100%), 433(M-TMSOH-SC), 393(M-245), 368(M-2TMSOH), 343(M-2TMSOH-SC), 253((M-3TMSOH-SC), 243(Ref. 0136)


A microbial transformation product of deoxycholic acid by Penicillium sp ATCC 12556.(Ref. 0136)




[0004] / [0136]
301
5a-Petromyzonol
5a-Cholane-3a,7a,12a,24-tetrol
 BBA0301
Mizuho Une
C24H42O4 394.588 Download ChemDraw structure file

224-226 and 240-241(Ref. 0301)
[a]d-25=+27.5(Ref. 0301)
(Ref. 0301)
(Ref. 0301)
(Ref. 0301)


Bile from Petromyzon marinus (Ref. 0301)Bile from Neoceratodus forsteri (Ref. 0302)Bile from Protopterus aethiopicus (Ref. 0302)
(Ref. 0301)



[0301] / [0302]
302
26,27-Dinor-5b-cholestane-3a,7a,12a,24,25-pentol
 BBA0302
Mizuho Une
C25H44O5 424.614 Download ChemDraw structure file

188(Ref. 0304)
(Ref. 0304)

as TMS derivative (Ref. 0303)


Bile from cholestatic patient(Ref. 0303)
(Ref. 0304)



[0303] / [0304]
303
3-Epi-16-deoxymyxinol
5a-Cholestane-3a,7a,26-triol
 BBA0303
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

187-188(Ref. 0305)
(Ref. 0305)
(Ref. 0305)



Bile from Heptatretus burgeri(Ref. 0305)
(Ref. 0305)



[0305]
304
3-Epimyxinol
5a-Cholestane-3a,7a,16a,26-tetrol
 BBA0304
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

178(Ref. 0305)
(Ref. 0305)
(Ref. 0305)



Bile from hagfish (Heptatretus burgeri)(Ref. 0305)




[0305]
305
a-Trichechol
5b-Cholestane-3a,6b,7a,25,26-pentol
 BBA0305
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

126-129(Ref. 0307)
(Ref. 0307)
(Ref. 0306/0307)
(Ref. 0306/0307)


Bile from west indian manatee, Trichechus manatus latirostris(Ref. 0306)
(Ref. 0307)



[0306] / [0307]
306
Arapaimol-A
5b-Cholestane-2b,3a,7a,12a,26-pentol
 BBA0306
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

216-220(Ref. 0308)
[a]d-25=+33.9pm2(Ref. 0308)
(Ref. 0308)
(Ref. 0308)
(Ref. 0308)


Bile from Arapaima gigas(Ref. 0308), Bile from Cardioglossa leucomystax , Hyperolius fusciventris burtoni, Hyperolius guttulatus, Hyperolius nitidulus (Ref. 0309)




[0308] / [0309]
307
Arapaimol-B
5b-Cholestane-2b,3a,7a,12a,26,27-hexol
 BBA0307
Mizuho Une
C27H48O6 468.666 Download ChemDraw structure file

228-230(Ref. 0308)
[a]d-25=+29.6pm2(Ref. 0308)
(Ref. 0308)
(Ref. 0308)
(Ref. 0308)


Bile from Arapaima gigas(Ref. 0308)




[0308]
308
5a-Dermophol
5a-Cholestane-3a,7a,12a,25,26,27-hexol
 BBA0308
Mizuho Une
C27H48O6 468.666 Download ChemDraw structure file

262-263(Ref. 0311)
(Ref. 0310/0311)
(Ref. 0311)
(Ref. 0310/0311)


Bile from Diemyctylus pyrrhogaster(Ref. 0310), Amphiuma means(Ref. 0310), Megalobactrachus japonicus (Ref. 0310)
(Ref. 0311)



[0310] / [0311]
309
5b-Dermophol
5b-Cholestane-3a,7a,12a,25,26,27-hexol
 BBA0309
Mizuho Une
C27H48O6 468.666 Download ChemDraw structure file

166-169(Ref. 0310)
(Ref. 0310)
(Ref. 0310)
(Ref. 0310)


Bile from Dermophis mexicanus(Ref. 0310), Bufo. formosus(Ref. 0310)
(Ref. 0310)



[0310]
310
27-Deoxy-5a-Cyprinol
5a-Cholestane-3a,7a,12a,26-tetrol
 BBA0310
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

232(Ref. 0312/0313)
[a]d-23=+39(C=0.2, ethanol)(Ref. 0312)
(Ref. 0313)




Bile from carp, Cyprinus carpio(Ref. 0312)Bile from Bufo B. Formosus, Bufo B. vulgaris (Ref. 0309/0314)Bile from Arthroleptis, Hylarana albolabris, Dicroglossus occipitalis, Ptychadena aequiplicata , Ptychadena mascareniensis, Ptychadena taenioscelis, Hyperolius guttulatus(Ref. 0309)Bile from Alligator mississippiensis (Ref. 0316)Bile from lungfishes,Lepidosiren, Neoceratodos, and Protopterus(Ref. 0302)Bile from coelacanth, Latimeria chalumae smith(Ref. 0302)Bile from Barbus trachypterus, Varicorhinus upembensis (Ref. 0315)
(Ref. 0313)



[0302] / [0309] / [0312] / [0313] / [0314] / [0315] / [0316]
311
Latimerol
5a-Cholestane-3b,7a,12a,26,27-pentol
 BBA0311
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

235-236(Ref. 0317)
[a]d-25=+33pm2(C=1.1, ethanol)(Ref. 0317)
(Ref. 0317)

as TMS derivatives(Ref. 0318)


Bile from Lathimeria chalumae (Ref. 0302/0317/0318)




[0302] / [0317] / [0318]
312
Myxinol
5a-Cholestane-3b,7a,16a,26-tetrol
 BBA0312
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

204-206(Ref. 0305/0319)
[a]D=-15pm2(C=1.2, ethanol)(Ref. 0319)
(Ref. 0319/0305)
(Ref. 0320/0321/0305)
(Ref. 0320/0321)


Bile from Eptatretus stoutii(Ref. 0319)Bile from Myxine glutinosa(Ref. 0319)




[0305] / [0319] / [0320] / [0321]
313
16-Deoxymyxinol
5a-Cholestane-3b,7a,26-triol
 BBA0313
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

218-219(Ref. 0322) or 206-207(Ref. 0324)
[a]D=+13pm3 (C=0.92, ethanol)(Ref. 0322)
(Ref. 0322)
(Ref. 0323/0305)
(Ref. 0323/0324)


Bile from Eptatretus stoutii(Ref. 0322)Bile from Myxine glutinosa(Ref. 0322)Bile from Heptatretus burgeri(Ref. 0305)
(Ref. 0324)



[0305] / [0322] / [0323] / [0324]
314
3-Epi-5a-bufol
5a-Cholestane-3b,7a,12a,25,26-pentol
 BBA0314
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

253(Ref. 0318)
(Ref. 0318)
(Ref. 0318)
(Ref. 0318)


Bile from coelacanth, Latimeria chalumnae(Ref. 0318)
(Ref. 0318)



[0318]
315
26-Deoxy-5a-chimaerol
5a-Cholestane-3a,7a,12a,24-tetrol
 BBA0315
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

(Ref. 0325)

(Ref. 0325)


Bile from rabbit(Ref. 0325)Bile from Neoceratodus forsteri(Ref. 0302)Bile from Barbus trachypterus, Varicorhinus upembensis, Labeo cf. clariensis (Ref. 0315)Bile from human (Ref. 0326), Cerebrotendinous xanthomatosis patient(Ref. 0327)




[0302] / [0315] / [0325] / [0326] / [0327]
316
27-Deoxy-5b-cyprinol
5b-Cholestane-3a,7a,12a,26-tetrol
 BBA0316
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

200-201(Ref. 0328/0329)
[a]d-23=+36.1pm1(25R), +25pm2(25S)(Ref. 0329)

as DMES derivative (Ref. 0331/0332>


Bile from Rana tigrina ruglosa(Ref. 0330)Urine from patients with cholestasis(Ref. 0331/0332)Human bile(Ref. 0326)Xenopus mulleri(Ref. 0309)Bile from Bufo B. formosus, Bufo B. vulgaris, Bufo maculatus, Bufo marinus, Bufo regularis Arthroleptis, Cardioglossa luecomystax, Dicroglossus occipitalis, Ptychadena aequiplicata, Ptychadena longirostris, Ptychadena maccarthyensis, Ptychadena mascareniensis, Ptychadena oxyrhynchus, Rana ridibunda, Hyperolius concolor ibadensis, Hyperolius fusciventris vurtoni, Hyperolius guttulatus, Hyperolius nitidulus(Ref. 0309)
(Ref. 0328/0329/0454/0467)



[0309] / [0326] / [0328] / [0329] / [0330] / [0331] / [0332] / [0454] / [0467]
317
3a,7a,12a-Trihydroxy-27-nor-5a-cholestan-24-one
 BBA0317
Mizuho Une
C26H44O4 420.625 Download ChemDraw structure file


as TMS derivative(Ref. 0333)


Bile from bullfrogs, Rana catesbeiana(Ref. 0333)
(Ref. 0334)



[0333] / [0334]
318
3a,7a,12a-Trihydroxy-27-NOR-5b-cholestan-24-one
 BBA0318
Mizuho Une
C26H44O4 420.625 Download ChemDraw structure file

(Ref. 0333)

as TMS derivative(Ref. 0333)


Bile from bullfrog, Rana catesbeiana(Ref. 0333)Human bile(Ref. 0326)
(Ref. 0334)



[0326] / [0333] / [0334]
319
5b-Petromyzonol
5b-Cholane-3a,7a,12a,24-tetrol
 BBA0319
Mizuho Une
C24H42O4 394.588 Download ChemDraw structure file

234.5-235.5(Ref. 0335)
(Ref. 0335)
(Ref. 0335)



Bile from Protopterus aethiopicus(Ref. 0302)Human bile(Ref. 0326)
(Ref. 0335)



[0302] / [0326] / [0335]
320
3a,7a,12a-Trihydroxy-26,27-dinor-5b-cholestane-24-one
 BBA0320
Mizuho Une
C25H42O4 406.599 Download ChemDraw structure file

166-168(Ref. 0336)

as TMS derivative(Ref. 0303)


Bile from a patient with cholestasis(Ref. 0303)
(Ref. 0336)



[0303] / [0336]
321
5a-Bufol
5a-Cholestane-3a,7a,12a,25,26-pentol
 BBA0321
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

241(Ref. 0337)
(Ref. 0337)




Latimeria chalumnae, Lepidosiren paradoxa, Neoceratodus forsteri (Ref. 0302)Hylarana albolabris, Ptychadena mascareniensis, Ptychadena taenioscelis, Rana galamensis (Ref. 0309)Amphiuma means(Ref. 0310)Diemyctylus phyrrhogaster(Ref. 0337)Rana erythrea (Ref. 0330)
(Ref. 0337)



[0302] / [0309] / [0310] / [0330] / [0337]
322
5b-Bufol
5b-Cholestane-3a,7a,12a,25,26-pentol
 BBA0322
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

178.5(Ref. 0338/0339)
[a]d-30=+38(Ref. 0338)
(Ref. 0338/0339)
(Ref. 0335)
(Ref. 0340/0350)


Bile from Bufo B. formosus (Ref. 0309/0310/0335/0338>Bile from Rana limnocharis(Ref. 0340)Bile from Discoglossus pictus, Bufo B. vulgaris, Bufo maculatus, Bufo marinus, Bufo regularis Arthroleptis, Dicroglossus occipitalis, Ptychadena aequiplicata, Ptychadena longirostris, Ptychadena maccarthyensis, Ptychadena mascareniensis, Ptychadena oxyrhynchus, Hyperolius concolor ibadensis, Hyperolius fusciventris vurtoni, Hyperolius guttulatus(Ref. 0309)Rana tigrina rugulosa(Ref. 0330)Rabbit bile(Ref. 0325)Healthy human bile(Ref. 0326), urine(Ref. 0351/0352), serum(Ref. 0355)Cerebrotendinous xanthomatosis : feces(Ref. 0327/0353)Extrahepatic cholestasis (Ref. 0332)Patients with Liver dysfunction : urine(Ref. 0354), serum(Ref. 0356)
(Ref. 0350)



[0309] / [0310] / [0325] / [0326] / [0327] / [0330] / [0332] / [0335] / [0338] / [0339] / [0340] / [0350] / [0351] / [0352] / [0353] / [0354] / [0355] / [0356]
323
5b-Ranol
27-Nor-5b-cholestane-3a,7a,12a,24,26-pentol
 BBA0323
Mizuho Une
C26H46O5 438.640 Download ChemDraw structure file

189(Ref. 0341) or 195.5-196.5(Ref. 0342) or 192(Ref. 0334)
[a]D=+30 (C=1.02, methanol)(Ref. 0342)
(Ref. 0341/0342)
(Ref. 0341/0342)



Bile from Discoglossus pictus, Arthroleptis, Ptychadena aequiplicata, Aubria subsigillata, Rana pipiens(Ref. 0309)Rana catesbeiana(Ref. 0334/0341/0342)Rana japonica japonica (Ref. 0330)
(Ref. 0341/0342/0343)



[0309] / [0330] / [0334] / [0341] / [0342] / [0343]
324
5a-Ranol
27-Nor-5a-cholestane-3a,7a,12a,24,26-pentol
 BBA0324
Mizuho Une
C26H46O5 438.640 Download ChemDraw structure file

Gelatinous material (Tetra-acetate = 154-157(Ref. 0344) or 155(Ref. 0334)
[a]D=+21(ethanol)(Ref. 0344)
Tetra-acetate(Ref. 0344)
Tetra-acetate(Ref. 0345)
(Ref. 0345)


Bile from Rana temporaria(Ref. 0309/0330/0344)Bile from Rana catesbeiana(Ref. 0334)Bile from Rana amurensis coreana, Rana amurensis tsushimensis, Rana japonica japonica, Rana tagoi(Ref. 0330)




[0309] / [0330] / [0334] / [0344] / [0345]
325
5a-Chimaerol
5a-Cholestane-3a,7a,12a,24,26-pentol
 BBA0325
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

234-235(Ref. 0329)
[a]d-24=+33.5pm1(C=1.1, ethanol)(Ref. 0329)
(Ref. 0329)




Bile from Catostomus commersoni(Ref. 0329)Bile from Neoceratodus forsteri(Ref. 0302)Bile from Polypterus senegalus,Distichodus lususso,Labeo cf.clariensis, Labeo weeksii(Ref. 0315)




[0302] / [0315] / [0329]
326
5b-Chimaerol
5b-Cholestane-3a,7a,12a,24,26-pentol
 BBA0326
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

180-182(Ref. 0346)
[a]D=+41.5(C=1.2, ethanol)(Ref. 0346)
(Ref. 0347)
(Ref. 0301)



Bile from Chimaera monstrosa(Ref. 0346)Bile from Mustelus manazo(Ref. 0348)Bile from Dasybatus akajei(Ref. 0349)Urine from healthy human and patients with cholestasis(Ref. 0332)Bile from human(Ref. 0326)
(Ref. 0492)



[0301] / [0326] / [0332] / [0346] / [0347] / [0348] / [0349] / [0492]
327
5a-Cyprinol
5a-Cholestane-3a,7a,12a,26,27-pentol
 BBA0327
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

242(Ref. 0313/0357) or 242-244(Ref. 0358)
[a]d-23=+29pm2(C=1.7, ethanol)(Ref. 0358)
(Ref. 0357/0358)
(Ref. 0357/0360/0301)
(Ref. 0340)


Bile from Latimeria chalumnae, Lepidosiren paradoxa, Protopterus aethiopicus (Ref. 0302)Bile from Cyprinus carpio(Ref. 0313/0357/0358), Parasilurus asotus(Ref. 0361)Bile from Hylarana albolabris, Ptychadena mascareniensis, Ptychadena taenioscelis, Rana galamensis, Rana esculenta (Ref. 0309)Bile from Opsarichthys uncirosris, Pseudogobic esocinus, Ishikauia steenackeri, Hemibarbus barbus, Zacco platypus, Sarcocheilichthys variegatus, Tribolodon hakonensis hakonensis, Carassius carassius (Ref. 0359)Bile from coelacanth, Latimeria chalumenae(Ref. 0317/0318)Bile from salamander, Megalo batrachus japonicus(Ref. 0362)Bile from Rana tagoi, Rana japonica japonica, Rana erythrea(Ref. 0330), Rana catesbeiana (Ref. 0334), Rana rugosa(Ref. 0340)Bile from Alestes macrophthalmus, Distichodus sexfasciatus, Barbus eutaenia eutaenia, Barbus trachypterus, Barbus gestetneri, Varicorhinus upembensis (Ref. 0315)




[0301] / [0302] / [0309] / [0313] / [0315] / [0317] / [0318] / [0330] / [0334] / [0340] / [0357] / [0358] / [0359] / [0360] / [0361] / [0362]
328
5b-Cholestane-3a,7a,26-triol
 BBA0328
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

155-157(25R), 138-140(25S) (Ref. 0363)
[a]d-25=+15.9 (25R), [a]d-25=+8.8(25S)(Ref. 0363)
1H-NMR(CDCl3) 18-CH3=66.0, 19-CH3=90.0, 21-CH3=91.0, 27-CH3=92.5 (in Hz) (Ref. 0363)
M/Z : 546, 531,456,441,366,351, 255, 73 (as TMS derivative) (Ref. 0363)


Human bile (Ref. 0326)
(Ref. 0363)



[0326] / [0363]
329
5b-Cholestane-3a,7a,25-triol
 BBA0329
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

181-183 (Ref. 0364)
cm-1 3480,2925, 2860, 1465, 1378, 1160, 1150, 1070 and 980 (Ref. 0364)

m/z 621, 546, 531, 456, 441, 366, 351, 255, 253, 131(base peak). (as TMS derivative) (Ref. 0364)


Human bile (Ref. 0326)
(Ref. 0364)



[0326] / [0364]
330
5b-Cholestane-3a,7a,24-triol
 BBA0330
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

125-127(25R), 78-79(25S) (Ref. 0363)
[a]d-25=+25.8(25R), [a]d-25=+4(25S)(Ref. 0363)
1H-NMR: (25R); 18-CH3=66.0, 19-CH3=91.0, 21-CH3=91.0, 26,27-CH3=91.5, (25S); 18-CH3=65.0, 19-CH3=90.0, 21-CH3=88.5, 26,27-CH3=92.5. (in Hz) (Ref. 0363)
M/Z : 546, 531,503, 456, 441,413, 366, 351, 323, 255, 145(base peak), 73 (as TMS derivative). (Ref. 0363)


Human bile (Ref. 0326)
(Ref. 0363)



[0326] / [0363]
331
12-Deoxy-chimaerol
5b-Cholestane-3a,7a,24,26-tetrol
 BBA0331
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

noncrystaline material (Ref. 0365)
cm-1(CHCl3) 3350 (Ref. 0365)
1H-NMR:18-CH3=0.70, 19-CH3=0.96, 21-CH3=1.00, 27-CH3=1.23 (Ref. 0365)



Human bile (Ref. 0365)
(Ref. 0365)



[0365]
332
12-Deoxy-bufol
5b-Cholestane-3a,7a,25,26-tetrol
 BBA0332
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

200-202 (Ref. 0366)

m/z 724(M+), 621, 531, 441, 364, 351, 343, 255, 253, 219(base peak).( as TMS derivative) (Ref. 0306/0365/0366)


Human bile (Ref. 0365)Bile from manatee, Trichechus manatus latirostris. (Ref. 0306)
(Ref. 0365)



[0306] / [0365] / [0366]
333
12-Deoxy-cyprinol
5b-Cholestane-3a,7a,26,27-tetrol
 BBA0333
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

136.5-138 (Ref. 0365)
cm-1 3300 (Ref. 0365)
1H-NMR:18-CH3=0.70, 19-CH3=0.95, 21-CH3=0.93, 3b-H=3.75, 7b-H=3.97, 26- and 27-CH2=4.02 (Ref. 0365)
m/z 544, 529, 454, 364, 343, 255(base peak), 253. ( as TMS derivative) (Ref. 0365)


Human bile (Ref. 0365)
(Ref. 0365)



[0365]
334
b-Trichechol
5b-Cholestane-3a,6b,7b,25,26-pentol
 BBA0334
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file


m/z : 709, 632, 619, 542, 529, 452, 439, 363, 349, 341, 285, 219, 195(base peak). (as TMS derivative) (Ref. 0306)


Bile from manatee, Trichechus manatus latirostris (Ref. 0306)Rat bile (Ref. 0389)




[0306] / [0389]
335
w-Trichechol
5b-Cholestane-3a,6a,7b,25,26-pentol
 BBA0335
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file


m/z : 709, 632, 619, 542, 529, 452, 439, 363, 285, 219, 195(base peak). (as TMS derivative) (Ref. 0306)


Bile from manatee, Trichechus manatus latirostris (Ref. 0306)




[0306]
336
5b-Cholestane-3a,6b,7a,26-tetrol
 BBA0336
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file


634, 544, 529, 489, 454, 441, 285, 253, 195(base peak). (as TMS derivative) (Ref. 0306)


Bile from manatee, Trichechus manatus latirostris (Ref. 0306)




[0306]
337
3a,12a,25-Trihydroxy-5b-cholestan-7-one
 BBA0337
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

cm-1 (KBr) 3350, 1695 (Ref. 0327)
1H-NMR(pyridine-d5):18-CH3=0.77, 19-CH3=1.02, 21-CH3=1.20, 26- and 27-CH3=1.39, 3b-H=3.75, 12b-H=4.24, (Ref. 0327)
m/z 560, 470, 380, 359, 341, 269, 251, 131(base peak). (Ref. 0327)


Bile and feces from patients with Cerebrotendinous xanthomatosis (Ref. 0327)
(Ref. 0327)



[0327]
338
5b-Cholestane-3a,7a,12a,24,25,26-hexol
 BBA0338
Mizuho Une
C27H48O6 468.666 Download ChemDraw structure file

204-209 (24R), 208-209 (24S) (Ref. 0367)
1H-NMR: 18-CH3=0.80, 19-CH3=0.98, 21-CH3=1.23, 27-CH3=1.53, 3b-H, 7b-H, 12b-H,24-H=3.40-4.50, 26-H2=4.00 (24R); 18-CH3=0.77, 19-CH3=0.95, 21-CH3=1.20, 27-CH3=1.45, 3b-H, 7b-H, 12b-H,24-H=3.40-4.50, 26-H2=3.92 (24S) (Ref. 0367)



Humane urine (Ref. 0367)Human serum (Ref. 0355)Urine from a patient with liver disease (Ref. 0354)
(Ref. 0367)



[0354] / [0355] / [0367]
339
5a-Cholestane-3a,7a,12a,25-tetrol
 BBA0339
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

Noncrystalline material (Ref. 0327)
1H-NMR(pyridine-d5):18-CH3=0.81, 19-CH3=0.89, 21-CH3=1.23, 26- and 27-CH3=1.36, 7b-H=4.05, 3b-H,12b-H=4.16 (Ref. 0327)
m/z 343, 253 (as TMS derivative) (Ref. 0327)


Urine and feces from a patient with Cerebrotendinous xanthomatosis (Ref. 0327)
(Ref. 0367)



[0327] / [0367]
340
5b-Cholestane-3a,7a,12a,22,25-pentol
 BBA0340
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

253-255 (22R), 237-239 (22S) (Ref. 0368)
[a]D=+32(22R), [a]D=+16(22S)(Ref. 0368)
1H-NMR(pyridine-d5):18-CH3=0.84, 19-CH3=1.00, 21-CH3=1.40, 26- and 27-CH3=1.44, (22R), 18-CH3=0.86, 19-CH3=1.00, 21-CH3=1.39, 26- and 27-CH3=1.40, (22S) (Ref. 0368)
m/z 653, 563, 473, 453, 433, 383, 363, 343, 293, 261, 253, 171(base peak), 131,81, 73. (as TMS derivative) (Ref. 0368)


Bile and Urine from a patient with Cerebrotendinous xanthomatosis ( only 22S isomer)(Ref. 0368)
(Ref. 0368)



[0368]
341
27-Nor-5b-cholest-25-ene-3a,7a,12a,24-tetrol
 BBA0341
Mizuho Une
C26H44O4 420.625 Download ChemDraw structure file

195-197 (Ref. 0326)
cm-1 (KBr) 3450(OH), 1636,883(-CH=CH2) (Ref. 0326)
1H-NMR(pyridine-d5) 18-CH3=0.83, 19-CH3=1.00, 21-CH3=1.24, 3b-H=3.78, 7b-H=4.09, 12b-H=4.26, 24-H=4.35, 25-H=6.15, 26-CH2=5.35, 5.55 (Ref. 0326)
m/z 708, 618, 528, 481, 438, 349, 343, 294, 281, 253(base peak), 157, 129. (as TMS derivative) (Ref. 0326)


Human bile (Ref. 0326)
(Ref. 0326/0343)



[0326] / [0343]
342
5b-Cholane-3a,7a,23,24-tetrol
 BBA0342
Mizuho Une
C24H42O4 394.588 Download ChemDraw structure file

224.5-226.5 (Ref. 0326)
cm-1 (KBr) 3350(OH). (Ref. 0326)
1H-NMR(pyridine-d5) 18-CH3=0.74, 19-CH3=0.96, 21-CH3=1.11, 3b-H,7b-H, and 23-H=3.4-4.5, 24-CH2=3.90 (Ref. 0326)
m/z 579, 489,399,309(base peak), 283,267,255,199. (as TMS derivative) (Ref. 0326)


Human bile (Ref. 0326)
(Ref. 0326)



[0326]
343
5b-Cholestane-3a,7a,12a,23-tetrol
 BBA0343
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

232-233(23R), 189-191(23S) (Ref. 0369)
[a]D=+52(23R), [a]D=+41(23S)(Ref. 0369)
cm-1 (KBr) 3400(OH), 1080,1040,980,950,920 (23R), 3340(OH), 1080,1030,980,950,918 (23S) (Ref. 0369)
1H-NMR(pyridine-d5) 18-CH3=0.89, 26-and 27-CH3=1.00,1.03, 19-CH3=1.01, 21-CH3=1.39, 3b-H=3.70, 7b-H and 23-H=4.10, 12b-H=4.32 :(23R) , 18-CH3=0.88, 26-and 27-CH3=0.95,0.98, 19-CH3=1.00, 21-CH3=1.38, 3b-H=3.70, 7b-H and 23-H=4.10, 12b-H=4.32: (23S) (Ref. 0369)
m/z 724,667,634,544,454,364,253(base peak),159. (as TMS derivative) (Ref. 0369/0370)


Patient with Cerebrotendinous xanthomatosis; Bile (Ref. 0327/0371), urine (Ref. 0327), feces (Ref. 0327/0370)
(Ref. 0452)



[0327] / [0369] / [0370] / [0371] / [0452]
344
5b-Cholestane-3a,7a,12a,24-tetrol
 BBA0344
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

185-185.5(24R), 186-186.5(24S) (Ref. 0373)
[a]d-25=+39(24R), [a]d-24=+24(24S)(Ref. 0373)
cm-1 (KBr) 3500(OH) (Ref. 0373)

m/z 681,634,591,544,501,454,411,364,343,321,253,145(base peak),55. (as TMS derivative) (Ref. 0325)


Rabbit bile (Ref. 0325)Human bile (Ref. 0326)Cerebrotendinous xanthomatosis; bile (Ref. 0327/0371), urine (Ref. 0327), feces (Ref. 0327/0370)
(Ref. 0372/0373/0407)



[0325] / [0326] / [0327] / [0370] / [0371] / [0372] / [0373] / [0407]
345
26-Deoxy-5b-ranol
27-Nor-5b-cholestane-3a,7a,12a,24-tetrol
 BBA0345
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

196(24R), 184(24S) (Ref. 0334)
[a]D=+36(24R), [a]D=+27(24S)(Ref. 0334)
1H-NMR(pyridine-d5) (24R): 18-CH3=0.79, 19-CH3=0.99, 26-CH3=1.15, 21-CH3=1.27, 3b-H,7b-H,12b-H and 24-H=3.50-4.42.(24S):18-CH3=0.84, 19-CH3=1.02, 26-CH3=1.17, 21-CH3=1.28, 3b-H, 7b-H, 12b-H and 24-H=3.50-4.40 (Ref. 0343)
m/z 530, 515, 501, 440, 433, 425, 411, 351, 343, 335, 321, 281, 253, 131(base peak). (as TMS derivative) (Ref. 0343)


Bile from Rana catesbeiana (Ref. 0334)Bile from Rana japonica japonica (Ref. 0330)Bile from Discoglossus pictus, Xenopus mulleri, Athroleptis poecilonotus?, Cardioglossa leucomystax, Abria subsigillata, Dicroglossus occipitalis, Ptychadena aequiplicata, Ptychadena longirostris, Ptychadena maccarthyensis, Ptychadena mascareniensis, Ptychadena oxyrhynchus, Ptychadena taenioscelis, Rana pipiens (Ref. 0309)
(Ref. 0326/0334)



[0309] / [0326] / [0330] / [0334] / [0343]
346
26-Deoxy-5a-ranol
27-Nor-5a-cholestane-3a,7a,12a,24-tetrol
 BBA0346
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

162(24R, as 3,7,24-triacetate), 81(24S, as 3,7,24-triacetate) (Ref. 0334)
[a]D=+2(24R, as 3,7,24-triacetate), [a]D=+15(24S, 3,7,24-triacetate) (Ref. 0334)




Bile from Rana catesbeiana (Ref. 0334)Bile from Rana amurensis coreana, Rana amurensis tsushimensis, Rana temporaria coreana, Rana temporaria tsushimensis, Rana japonica japonica, Rana tagoi (Ref. 0330)Bile from Cardioglossa leucomystax, Hylarana albolabris, Dicroglossus occipitalis, Ptychadena aequiplicata, Ptychadena longirostris, Ptychadena maccarthyensis, Ptychadena mascareniensis, Ptychadena taenioscelis, Rana galamensis, Rana temporaria (Ref. 0309)




[0309] / [0330] / [0334]
347
5b-Cholestane-3a,7a,12a-triol
 BBA0347
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

186-187.5(Ref. 0374)
[a]D=+30.4 (Ref. 0380)

m/z 546,456,366(base peak),253. (as TMS derivative) (Ref. 0375)


Patients with Cerebrotendinous xanthomatosis: Bile (Ref. 0375), urine (Ref. 0327)
(Ref. 0372/0374)



[0327] / [0372] / [0374] / [0375] / [0380]
348
5b-Cholest-25-ene-3a,7a,12a-triol
 BBA0348
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

164 (Ref. 0339)
cm-1 (nujol) 3660(OH), 1650,883(CH2=C-) (Ref. 0339)




Bile from a patient with Cerebrotendinous xanthomatosis (Ref. 0375)
(Ref. 0339/0493)



[0339] / [0375] / [0493]
349
27-Nor-5a-cholestane-3a,7a,12a,24,25,26-hexol
 BBA0349
Mizuho Une
C26H46O6 454.640 Download ChemDraw structure file

174-175 (Ref. 0326)
cm-1 (KBr) 3350(OH) (Ref. 0326)
1H-NMR 18-CH3=0.80, 19-CH3=0.99, 21-CH3=1.32, 3b-H,7b-H,12b-H, 24,25,and 26-H =3.50-4.40. (Ref. 0326)
m/z 769,681,591,501,411,343,321(base peak),281,253,204,191,156,129,116. (as TMS derivative) (Ref. 0326/0381)


Human bile (Ref. 0326)Human urine (Ref. 0367/0381)Human serum (Ref. 0355)Urine from a patient with liver disease (Ref. 0354)




[0326] / [0354] / [0355] / [0367] / [0381]
350
5b-Cholestane-3a,7a,12a,25-tetrol
 BBA0350
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

188-189 (Ref. 0376), 189.5-191 (Ref. 0377)
[a]D=+36.8(Ref. 0380)
(Ref. 0380)
m/z 724,709,634,619,544,529,454,439,364,349,131(base peak). (as TMS derivative) (Ref. 0377)


A patient with Cerebrotendinous xanthomatosis: Bile (Ref. 0327/0371/0375), urine (Ref. 0327/0378), feces (Ref. 0327/0370/0377).Human bile (Ref. 0326)Rabbit bile (Ref. 0325)Bile from Alligator mississippiensis (Ref. 0316)
(Ref. 0350/0376/0493/0494)



[0316] / [0325] / [0326] / [0327] / [0350] / [0370] / [0371] / [0375] / [0376] / [0377] / [0378] / [0380] / [0493] / [0494]
351
5b-Cholestane-3a,7a,12a,23,25-pentol
 BBA0351
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

209-210(23S) (Ref. 0379)
[a]d-25=+49(23S)
cm-1 (CHCl3) 3340(OH), 1075,1020,990,920,894. (Ref. 0379/0380)
1H-NMR(pyridine-d5) 18-CH3=0.82, 19-CH3=0.96, 21-CH3=1.38, 26 and 27-CH3=1.44 and 1.50, 3b-H,7b-H,12b-H, and 23-H =3.40-4.60. (Ref. 0379/0380)
m/z 722,667,632,577,550,542,487,460,452,397,370,362,344,307,281.253,199,143,131(base peak). (as TMS derivative) (Ref. 0379/0380)


Cerebrotendinous xanthomatosis: bile (Ref. 0327/0371), urine (Ref. 0327/0378), feces (Ref. 0327/0370/0377)
(Ref. 0350/0379/0452)



[0327] / [0350] / [0370] / [0371] / [0377] / [0378] / [0379] / [0380] / [0452]
352
5b-Cholestane-3a,7a,12a,24,25-pentol
 BBA0352
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

212-214(24R), 203-205(24S) (Ref. 0380)
[a]D=+44.8(24R), [a]D=+28.7(24S) (Ref. 0380)
cm-1 (CHCl3) 3420(OH) (Ref. 0380)
1H-NMR(CD3OD) 18-CH3=72.4, 19-CH3=92.2, 21-CH3=103.6, 26 and 27-CH3=114.4 and 116.8 (in Hz) (Ref. 0380)
m/z 812,797,722,707,681,632,617,591,543,527,501,453,437,411,363,347,343,321,281,253,147,143,131(base peak) (as TMS derivative) (Ref. 0351/0380)


Cerebrotendinous xanthomatosis: bile (Ref. 0327/0371), urine (Ref. 0327/0378), feces (Ref. 0327/0370/0377/0380)Human bile (Ref. 0326), urine (Ref. 0351/0367), serum (Ref. 0355)Urine from patients with liver disease(Ref. 0354)
(Ref. 0339/0493)



[0326] / [0327] / [0339] / [0351] / [0354] / [0355] / [0367] / [0370] / [0371] / [0377] / [0378] / [0380] / [0493]
353
Scymnol
5b-Cholestane-3a,7a,12a,24,26,27-hexol
 BBA0353
Mizuho Une
C27H48O6 468.666 Download ChemDraw structure file

120-123 (Ref. 0347)
[a]D=+34 (Ref. 0347)
cm-1 (CHCl3) 3400(OH) (Ref. 0347)




Bile from shark (Ref. 0347/0348) and sting-ray (Ref. 0349)
(Ref. 0347)



[0347] / [0348] / [0349]
354
27-Nor-5b-cholestane-3a,7a,12a,24,25-pentol
 BBA0354
Mizuho Une
C26H46O5 438.640 Download ChemDraw structure file

230(Ref. 0351), 194-200 (Ref. 0353)
cm-1 (KBr) 3400(OH) (Ref. 0351), cm-1 (nujol) 3440(OH) (Ref. 0353)
1H-NMR(pyridine-d5) 18-CH3=0.82, 19-CH3=1.00, 21-CH3=1.26, 26-CH3=1.52, 3b,7b,12b,24,25-H=3.55-4.40 (Ref. 0380)
m/z 798,708,693,681,618,603,591,528,513,501,438,411,371,348,343,321(base peak),281,253,219,129,117. (as TMS derivative) (Ref. 0351/0353/0382)


Human bile (Ref. 0326), urine (Ref. 0351/0352/0367/0382), serum (Ref. 0355)Urine from a patient with Cerebrotendinous xanthomatosis (Ref. 0327)Urine from a patient with liver disease (Ref. 0354)Serum from a patient with liver disease (Ref. 0356)Urine and feces from a patient with Sitosterolemia (Ref. 0353)Urine from a patient with cholestasis (Ref. 0331) and extrahepatic cholestasis (Ref. 0332)Rat bile(Ref. 0389)
(Ref. 0351/0353)



[0326] / [0327] / [0331] / [0332] / [0351] / [0352] / [0353] / [0354] / [0355] / [0356] / [0367] / [0380] / [0382] / [0389]
355
24-Nor-5b-cholestane-3a,7a,12a,25-tetrol
 BBA0355
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

124-126 (Ref. 0383)
cm-1 (KBr) 3400(OH) (Ref. 0383)
1H-NMR(CDCl3) 18-CH3=0.65, 19-CH3=0.85, 21-CH3=0.95, 26 and 27-CH3=1.16, (Ref. 0383)
m/z 620,565,530,440,384,294,253,131(base peak). (as TMS derivative) (Ref. 0303/0325/0383)


Bile from a patient with cholestasis (Ref. 0303)Rabbit bile (Ref. 0325)Human bile (Ref. 0326)
(Ref. 0383)



[0303] / [0325] / [0326] / [0383]
356
5b-Cyprinol
5b-Cholestane-3a,7a,12a,26,27-pentol
 BBA0356
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

173-174 (Ref. 0384), 175-177(Ref. 0385)
[a]D=+35.5 (Ref. 0385)
cm-1 (nujol) 3400(OH) (Ref. 0384)
1H-NMR(d7-DMF) 18-CH3=41.0 cps, 19-CH3=52.5 cps. (Ref. 0386)



Bile from Conger myriaster (Ref. 0387)Bile from Sturgeons (Acipenseridae) and paddlefish Polyodon spathula (Ref. 0385)Bile from Rana nigromaculata (Ref. 0388)Bile from Rana brevipoda (Ref. 0340)Bile from Xenopus laevis (Ref. 0309/0340)Bile from Rana plancyi, Rana tigrina ruglosa (Ref. 0330)Bile from Discoglossus pictus, Xenopus mulleri, Arthroleptis poecilonotus, Dicroglossus occipitalis, Ptychadena aequiplicata, Ptychadena longirostris, Ptychadena maccarthyensis, Ptychadena mascareniensis, Ptychadena oxyrhynchus, Rana esculenta, Rana ridibunda, Hyperolius concolor ibadensis, Hyperolius fusciventris vurtoni, Hyperolius guttulatus, Hyperolius nitidulus (Ref. 0309)Bile from healthy human (Ref. 0326)Urine from healthy human (Ref. 0351)Urine from patients with cholestasis (Ref. 0331) and extrahepatic cholestasis (Ref. 0332)Bile from some fishes, Polypterus endlicheri congicus, Polypterus ornatipinnis, Polypterus senegalus, Alestes macrolepidotus, Schilbe mystus (Ref. 0315)
(Ref. 0384/0385)



[0309] / [0315] / [0326] / [0330] / [0331] / [0332] / [0340] / [0351] / [0384] / [0385] / [0386] / [0387] / [0388]
357
26,27-Dinor-5b-Cholestane-3a,7a,12a,24-tetrol
 BBA0357
Mizuho Une
C25H44O4 408.614 Download ChemDraw structure file

179-180(24R), 192-193(24S) (Ref. 0390)
[a]D=+40 (24R), [a]D=+33 (24S) (Ref. 0385)
cm-1 (KBr) 3340(OH), 1080, 1030,980,950,918 (Ref. 0390)
1H-NMR(pyridine-d5) 18-CH3=0.83, 19-CH3=1.02, 21-CH3=1.25, 25-CH3=1.35, 3b,7b,12b,24-H=3.70-4.35(Ref. 0390)
m/z 696,606,516,426,343,337,253. (as TMS derivative) (Ref. 0390)


Arthroleptis poecilonotus?, Aubria subsigillata, Dicroglossus occipitalis, Rana pipiens (Ref. 0309)
(Ref. 0390)



[0309] / [0385] / [0390]
358
3a,7a,12a,24-Tetrahydroxy-24-methyl-5b-cholestan-26-oic acid
 BBA0358
Mizuho Une
C28H48O6 480.677 Download ChemDraw structure file

144 (Methyl ester) (Ref. 0391)

m/z (relative intensity) 767(9%), 692(4%), 602(31%), 512(25%),422(14%), 343(22%),2 81(11%), 253(17%), 203(100%). (as methyl ester-TMS derivative) (Ref. 0392)


Bile from Bufo vulgaris formosus (Ref. 0392)
(Ref. 0391)



[0391] / [0392]
359
3a,7a,12a-Trihydroxy-24-methyl-5b-Cholestan-26-oic acid
 BBA0359
Mizuho Une
C28H48O5 464.678 Download ChemDraw structure file

192 (Ref. 0391)

m/z (relative intensity) 679(4%), 604(4%), 514(25%), 499(4%), 424(56%), 409(8%), 343(40%), 317(15%), 281(24%), 253(100%). (as methyl ester-TMS derivative) (Ref. 0333)


Bile from Rana catesbeiana (Ref. 0333)
(Ref. 0391)



[0333] / [0391]
360
3a,7a,12a-Trihydroxy-5b-cholest-22-ene-24-carboxylic acid
 BBA0360
Mizuho Une
C28H46O5 462.662 Download ChemDraw structure file

160 (Ref. 0394)

m/z (relative intensity) 692(6%), 602(29%), 512(23%), 422(28%), 343(22%), 315(7%), 253(100%). (as methyl ester-TMS derivative) (Ref. 0392)


Bile from Bufo vulgaris formosus (Ref. 0392/0393/0394)




[0392] / [0393] / [0394]
361
3a,7a,12a-Trihydroxy-5a-cholest-22-ene-24-carboxylic acid
 BBA0361
Mizuho Une
C28H46O5 462.662 Download ChemDraw structure file


m/z (relative intensity) 692(10%), 602(49%), 512(27%), 422(7%), 343(49%), 315(37%), 253(100%). (as methyl ester-TMS derivative) (Ref. 0392)


Bile from Bufo vulgaris formosus (Ref. 0392)




[0392]
362
Arapaimic acid
2b,3a,7a,12a-Tetrahydroxy-5b-cholestan-26-oic acid
 BBA0362
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file

244-248 (Ref. 0308)
1H-NMR(CDCl3) 18-CH3=0.775 19-CH3=1.03 , 21-CH3=1.17(d, J=5.5Hz), 27-CH3=1.29(d, J=6.5Hz), 2a-H=4.0-4.4, 3b-H= 3.5-3.9, 7b-H=4.08, 12b-H=4.20. (Ref. 0308)
m/z 648(M+), 528, 468, 431, 408, 371, 311, 251. (as tetraacetate-methyl ester)


Bile from Arapaima gigas (Ref. 0308)




[0308]
363
3a,7a,12a,22-Tetrahydroxy-5b-cholestan-26-oic acid
 BBA0363
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file

220 (as lactone form) (Ref. 0395)
cm-1 (nujol) 3300(OH), 1710 (Ref. 0396)
As Lactone: 1H-NMR(CDCl3) 19-CH3=0.68, 18-CH3=0.87 , 21-CH3=1.11(d, J=6.5Hz), 27-CH3=1.30(d, J=6.5Hz), 25-H=2.40(ddq, J=11.5,6.2 and 6.8Hz), 22-H=4.42(dd,J=11.7 and 3.2Hz), (Ref. 0395); As methyl ester (pyridine-d5) 18-CH3=0.90, 19-CH3=1.03, 21-CH3=1.40, 27-CH3=1.22, 3b-H=~3.7, 7b-H=4.11, 12b-H=4.35, 22-H=~4.00 (Ref. 0397)
m/z 383,293,253,217,185,127. (as methyl ester-TMS ether derivative) (Ref. 0397)m/z 574,559,484,469,394,343,281,253,113 (as TMS ether of lactone form) (Ref. 0397)


(22S)-isomer was found inBile from Amyda japonica (22S isomer)(Ref. 0395/0396)Bile from Chelonia mydas (Ref. 0397)(22R)-isomer was found inUrine from a patient with Zellweger syndrome.(Ref. 0398)




[0395] / [0396] / [0397] / [0398]
364
3a,7a,12a,24-Tetrahydroxy-5a-cholestan-26-oic acid
 BBA0364
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file

cm-1 (KBr) 3340(OH), 1710(COOH) (Ref. 0333)

m/z 753,588,498,343,253. (as methyl ester-TMS ether derivative) (Ref. 0333)


Bile from Rana catesbeiana (Ref. 0333)
(Ref. 0333)



[0333]
365
3a,7a,12a,23-Tetrahydroxy-5b-cholestan-26-oic acid
 BBA0365
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file


m/z 574,559,484,469,394,379,343,253. (as TMS ether derivative of the lactone form) (Ref. 0398)


Urine from a patient with Zellweger syndrome (Ref. 0398/0399)




[0398] / [0399]
366
3b,7a,12a-Trihydroxy-5a-cholestan-26-oic acid
 BBA0366
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file

228-229 (Ref. 0318)
cm-1 (KBr) 3400(OH), 1730(COOH) (Ref. 0318)
1H-NMR(pyridine-d5) 18-CH3=0.80, 19-CH3=0.90, 21-CH3=1.23(d,J=6Hz), 27-CH3=1.32(d.J=6Hz), 3a-H=3.80, 7b-H=4.09, 12b-H=4.23 (Ref. 0318)
m/z 693,318,514,483,411,357,303,253 (as methyl ester-TMS ether derivative) (Ref. 0318)


Bile from coelacanth Latimeria chalumnae (Ref. 0318)
(Ref. 0318)



[0318]
367
1b,3a,7a,12a-Tetrahydroxy-5b-cholestan-26-oic acid
 BBA0367
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file


m/z 588,498,408,341,251,217. (as methyl ester-TMS ether derivative) (Ref. 0400)


Bile from Alligator mississippiensis. (Ref. 0400)Urine from a patient with Zellweger syndrome (Ref. 0399/0404/0425)




[0399] / [0400] / [0404] / [0425]
368
3a,7b,12a-Trihydroxy-5b-cholestan-26-oic acid
 BBA0368
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file

90-92 (Ref. 0400)
cm-1 (KBr) 3400(OH), 1720(COOH) (Ref. 0400)
1H-NMR(pyridine-d5) 18-CH3=0.82, 19-CH3=1.00, 21-CH3=1.13(d,J=6Hz), 27-CH3=1.17(d,J=6Hz), 3b-H and 7a-H=3.78, 12b-H=4.16, COOCH3=3.57 (Ref. 0400)
m/z 665,590,500,433,410,343,281,253,243 (as methyl ester TMS ether derivative) (Ref. 0400)


Bile from Alligator mississippiensis (Ref. 0400)
(Ref. 0400)



[0400]
369
7b,12a-Dihydroxy-3-oxo-5b-cholestan-26-oic acid
 BBA0369
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file


m/z 591,516,426,269,251 (as methyl ester-TMS ether derivative) (Ref. 0400)


Bile from Alligator mississippiensis (Ref. 0400)




[0400]
370
7a,12a-Dihydroxy-3-oxo-5b-cholestan-26-oic acid
 BBA0370
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file

168-170 (as methyl ester) (Ref. 0400)
cm-1 (KBr) 3400(OH), 1735, 1700. (Ref. 0400)
1H-NMR(pyridine-d5) 18-CH3=0.80, 19-CH3=0.97, 21-CH3 and 27-CH3=1.11(d,J=6Hz), COOCH3=3.50, 7b-H=3.99, 12b-H=4.15. (Ref. 0400)



Bile from Alligator mississippiensis (Ref. 0316/0400)
(Ref. 0400)



[0316] / [0400]
371
7a,12a-Dihydroxy-3-oxo-5a-cholestan-26-oic acid
 BBA0371
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file





Bile from Alligator mississippiensis (Ref. 0316)
(Ref. 0318)



[0316] / [0318]
372
3a,12a-Dihydroxy-7-oxo-5b-cholestan-26-oic acid
 BBA0372
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file

1H-NMR(pyridine-d5) 18-CH3=0.75, 21-CH3=1.13(d,J=6Hz), 27-CH3=1.15(d,J=6Hz), 19-CH3=1.17, COOCH3=3.57, 3b-H=3.72, 12b-H=4.12. (Ref. 0400)



Bile from Alligator mississippiensis (Ref. 0316/0400)
(Ref. 0400/0467)



[0316] / [0400] / [0467]
373
3b-Hydroxy-5b-cholestan-26-oic acid
 BBA0373
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file





Feces from Alligator mississippiensis (Ref. 0401)Serum from a patient with Zellweger syndrome (Ref. 0403)




[0401] / [0403]
374
3a-Hydroxy-5b-cholestan-26-oic acid
 BBA0374
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

169 (Ref. 0402), 169-170(25L)(Ref. 0411), 155-157(25D)(Ref. 0412), 100-105(methyl ester)(Ref. 0411), 112-113(25L,methyl ester)(Ref. 0412), 108-109(25D,methyl ester)(Ref. 0412)
[a]D=+43(25L), [a]D=+26 (25D) (Ref. 0412)
cm-1 (KBr) 3400(OH), 1710 (Ref. 0402)

m/z 504,489,414,399,383,257,230,215 (Ref. 0401)


Feces from Alligator mississippiensis (Ref. 0401)Serum from a patient with Zellweger syndrome (Ref. 0403)patient with cholestasis (Ref. 0411)
(Ref. 0402/0412)



[0401] / [0402] / [0403] / [0411] / [0412]
375
3b,12a-Dihydroxy-5b-cholestan-26-oic acid
 BBA0375
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file





Feces from Alligator mississippiensis (Ref. 0401)




[0401]
376
3a,12a-Dihydroxy-5b-cholestan-26-oic acid
 BBA0376
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

144-146 (Ref. 0400),
[a]D=+63(25L), [a]D=+47 (25D) (Ref. 0412)
cm-1 (KBr) 3400(OH), 1700 (Ref. 0400)
1H-NMR(pyridine-d5) 18-CH3=0.73, 19-CH3=0.95, 21-CH3=1.16(d,J=6Hz), 27-CH3=1.31(d,J=6Hz), 3b-H=3.80, 12b-H=4.22. (Ref. 0400)



Alligator mississippiensis; Feces (Ref. 0401), bile(Ref. 0316/0400)
(Ref. 0400/0412/0416)



[0316] / [0400] / [0401] / [0412] / [0416]
377
3b,7b-Dihydroxy-5b-cholestan-26-oic acid
 BBA0377
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file





Feces from Alligator mississippiensis (Ref. 0401)




[0401]
378
3a,7b-Dihydroxy-5b-cholestan-26-oic acid
 BBA0378
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

cm-1 (KBr) 3400(OH), 1700 (Ref. 0400)
1H-NMR(pyridine-d5) 18-CH3=0.70, 19-CH3=0.97, 21-CH3=0.97(d,J=6Hz), 27-CH3=1.26(d,J=6Hz), 3b-H and 7a-H=3.70 (Ref. 0400)



Alligator mississippiensis; Feces (Ref. 0401), bile(Ref. 0400)
(Ref. 0400)



[0400] / [0401]
379
3a,7a-Dihydroxy-5b-cholest-24-en-26-oic acid
 BBA0379
Mizuho Une
C27H44O4 432.636 Download ChemDraw structure file

214 (Ref. 0405)
cm-1 (KBr) 3400(OH), 1680,1640 (Ref. 0405)

m/z 590,575,559,500,410,395,345,283,255 (as methyl ester-TMS ether derivative) (Ref. 0406)


Bile from Varanus monitor (Ref. 0406)
(Ref. 0405/0450)



[0405] / [0406] / [0450]
380
3a,7a-Dihydroxy-5b-cholest-23-en-26-oic acid
 BBA0380
Mizuho Une
C27H44O4 432.636 Download ChemDraw structure file


m/z 590,575,500,463,410,373,345,283,255 (as methyl ester-TMS ether derivative) (Ref. 0406)


Bile from Varanus monitor (Ref. 0406)




[0406]
381
3a,12a,22-Trihydroxy-5b-cholestan-26-oic acid
 BBA0381
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file

1H-NMR(pyridine-d5) 18-CH3=0.83, 19-CH3=0.99, 21-CH3=1.38(d,J=6.5Hz), 27-CH3=1.22(d,J=7Hz), 3b-H=~3.90, 12b-H=~4.30, 22-H=4.01 (as methyl ester) (Ref. 0397)
m/z 665,385,345,295,255,217,185,127 (as methyl ester-TMS ether derivative) (Ref. 0397)m/z 576,471,396,345,283,255 (as lactone) (Ref. 0397)


Bile from Chelonia mydas (Ref. 0397)




[0397]
382
3a,7a,24-Trihydroxy-5b-cholestan-26-oic acid
 BBA0382
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file

cm-1 (CHCl3) 3300,1710 (Ref. 0365)
1H-NMR(pyridine-d5) 18-CH3=0.70, 19-CH3=0.95, 21-CH3=0.98(d,J=6Hz), 27-CH3=1.43(d,J=6Hz), COOCH3=3.60, 3b-H and 24-H=3.50-4.10, 7b-H=3.95, (as methyl ester) (Ref. 0365)
m/z 500,485,410,395,343,323,296,281,255,253,243,189 (as methyl ester-TMS ether derivative) (Ref. 0365)


Bile from Varanus monitor (Ref. 0406)Serum from patients with Zellweger syndrome (Ref. 0422/0423/0425)
(Ref. 0365)



[0365] / [0406] / [0422] / [0423] / [0425]
383
3b,7a,12a-Trihydroxy-5b-cholestan-26-oic acid
 BBA0383
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file





Feces from Alligator mississippiensis (Ref. 0401)




[0401]
384
3a,7a,12a-Trihydroxy-5b-cholest-24-en-26-oic acid
 BBA0384
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file

205-206(24E isomer) (Ref. 0407)
cm-1 (KBr) 3400,1682,1645 (Ref. 0407)
1H-NMR(pyridine-d5) 24E-isomer: 18-CH3=0.78, 19-CH3=0.97, 21-CH3=1.19(d,J=6Hz), 27-CH3=1.80, 3b-H=3.65, 7b-H=4.05, 12b-H=4.20, 24-H=7.13(t,J=6Hz).(Ref. 0407); 24Z-isomer: 18-CH3=0.78, 19-CH3=0.97, 21-CH3=1.19(d,J=6Hz), 27-CH3=1.80, 3b-H=3.65, 7b-H=4.05, 12b-H=4.20, 24-H=5.85(t,J=6Hz).(Ref. 0407)
m/z 678,663,588,573,551,498,461,408,371,343,281,253,251 (as methyl ester-TMS ether derivative) (Ref. 0406)


Bile from Varanus monitor (Ref. 0406)Human bile (Ref. 0408),serum(Ref. 0490)
(Ref. 0407/0450/0467)



[0406] / [0407] / [0408] / [0450] / [0467] / [0490]
385
3a,7a,12a-Trihydroxy-5b-cholest-23-en-26-oic acid
 BBA0385
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file

176-179 (Ref. 0409)
[a]d-12=+29.13, (C=1.16, ethanol)(Ref. 0409)

m/z 663,588,498,461,408,371,343,301,281,253 (as methyl ester-TMS ether derivative) (Ref. 0392)m/z 678,663,588,573,551,498,461,431,408,371,343,341,281,253,251(as methyl ester-TMS ether derivative) (Ref. 0406)


Bile from Bufo vulgaris japonicus (Ref. 0409)Bile from Bufo vulgaris formosus (Ref. 0392)Bile from Varanus monitor (Ref. 0406)Patient with Thiolase deficiency(Ref. 0490)




[0392] / [0406] / [0409] / [0490]
386
3a,7a-Dihydroxy-5b-cholestan-26-oic acid
 BBA0386
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

25D:175-176, 25L: non-crystakkine form (Ref. 0412)
25D:[a]D=+5, 25L:[a]D=+18, (Ref. 0412)
cm-1 (KBr) 3400,1700 (Ref. 0405)

m/z 448,430,412,397,273,264,255,245,228,213,201 (Ref. 0416)


Alligator mississippiensis; Bile (Ref. 0316/0400/0416), Feces (Ref. 0401)Patients with Zellweger syndrome; Bile(Ref. 0403/0423), urine(Ref. 0403/0419/0421), serum (Ref. 0420/0422/0423/0425), plasma(Ref. 0426)Refsum disease:plasma(Ref. 0426)Bile from kite Milvuslineatus lineatus (Ref. 0429)Human bile(Ref. 0441)
(Ref. 0405/0412/0416/0441/0482)



[0316] / [0400] / [0401] / [0403] / [0405] / [0412] / [0416] / [0419] / [0420] / [0421] / [0422] / [0423] / [0425] / [0426] / [0429] / [0441] / [0482]
387
Varanic acid
3a,7a,12a,24-Tetrahydroxy-5b-cholestan-26-oic acid
 BBA0387
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file

24S,25R-isomer:170-171, 24S,25S:173-175, 24R,25R:219-220, 24R,25S: 149-150 (Ref. 0407)
24S,25R:[a]D=+23.5, 24S,25S:[a]D=+26.7, 24R,25R:[a]D=+61.7, 24R,25S:[a]D=+44.6(Ref. 0407)
cm-1 (KBr) 3390,1715 (Ref. 0407)
(Ref. 0407)
m/z 753,588,498,408,343,321,281,253 (as methyl ester-TMS derivative)(Ref. 0333)


Bile from Varanus monitor (Ref. 0406), Varanus niloticus(Ref. 0430)Bile from Bombina orientalis(Ref. 0340/0431), Rana catesbeiana(Ref. 0333), Bufo vulgaris formosus(Ref. 0392),Patients with Zellweger syndrome:Urine (Ref. 0399/0419/0421/0423), Serum (Ref. 0403/0419/0422),plasma (Ref. 0426)
(Ref. 0407)



[0333] / [0340] / [0392] / [0399] / [0403] / [0406] / [0407] / [0419] / [0421] / [0422] / [0423] / [0426] / [0430] / [0431]
388
3a,7a,12a,26-Tetrahydroxy-5a-cholestan-27-oic acid
 BBA0388
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file

238-240(Ref. 0333)
cm-1 (KBr) 3300,1710 (Ref. 0333)
1H-NMR(pyridine-d5) 18-CH3=0.80, 19-CH3=0.90, 21-CH3=1.19(d,J=6Hz), 3b-H=4.09, 7b-H,12b-H, and 26-CH2=4.16-4.36 (Ref. 0333)
m/z 753,678,588,498,343,281,253 (as methyl ester-TMS ether derivative)(Ref. 0333)


Bile from Rana catesbeiana (Ref. 0333)
(Ref. 0333)



[0333]
389
3a,7a,12a,26-Tetrahydroxy-5b-cholestan-27-oic acid
 BBA0389
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file

268-269(Ref. 0330)
cm-1 (KBr) 3400,2940,1720 (Ref. 0330)
1H-NMR(pyridine-d5) 18-CH3=0.81, 19-CH3=1.01, 21-CH3=1.21(d,J=6Hz), 3b-H=3.76, 7b-H=4.16, 12b-H=4.28, 26-CH2=4.30 (Ref. 0330)
m/z 753,678,588,498,391,343,281,253 (as methyl ester-TMS ether derivative)(Ref. 0330)


Bile from Rana plancyi(Ref. 0330), Rana catesbeiana(Ref. 0333)Patients with Zellweger syndrome: urine(Ref. 0399), plasma(Ref. 0426)Infants with Refsum's disease:plasma(Ref. 0426)Human bile(Ref. 0408)Bile from Alligator mississippiensis (Ref. 0400)
(Ref. 0330)



[0330] / [0333] / [0399] / [0400] / [0408] / [0426]
390
3a,7a,12a-Trihydroxy-5a-cholestan-26-oic acid
 BBA0390
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file

225-226(Ref. 0427), 227-229(Ref. 0428)
[a]d-25=+41.7(Ref. 0427)
cm-1 (KBr) 3278,1710,1194,1123,1083,1035,1009,957,930,888,859,838 (Ref. 0427)

m/z 665,590,575,500,485,410,395,343,303,281,253 (Ref. 0333)


Bile from Iguana iguana (Ref. 0428)Bile from Rana temporaria coreana(Ref. 0330),Rana temporaria tsushimensis(Ref. 0330), Rana catesbeiana(Ref. 0333), Rana rugosa(Ref. 0340)Bile from Alligator mississippiensis (Ref. 0316/0400)
(Ref. 0427)



[0316] / [0330] / [0333] / [0340] / [0400] / [0427] / [0428]
391
3a,6a,7a,12a-Tetrahydroxy-5b-cholestan-26-oic acid
 BBA0391
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file

260-262(Ref. 0415)
1H-NMR(pyridine-d5) 18-CH3=0.81, 19-CH3=1.04, 21-CH3=1.22(d,J=6Hz), 27-CH3=1.34, 3b-H=3.68-3.84, 6b-H,7b-H, and 12b-H=4.22-4.31 (Ref. 0415)
m/z 588,498,409,341,251 (as methyl ester-TMS ether derivative) (Ref. 0415)


Patients with Zellweger syndrome: urine(Ref. 0399/0404), serum(Ref. 0422)
(Ref. 0415)



[0399] / [0404] / [0415] / [0422]
392
3b-Hydroxycholest-5-en-26-oic acid
 BBA0392
Mizuho Une
C27H44O3 416.636 Download ChemDraw structure file

97-100 (as methyl ester)(Ref. 0411)

m/z 502,446,412,373,291,255,129 (as methyl ester-TMS ether derivative) (Ref. 0403/0411/0444)


Patients with Zellweger syndrome: bile(Ref. 0403), serum(Ref. 0403)Human serum (Ref. 0444)Serum from 3b-hydroxy-D5-C27-steroiddehydrogenase deficiency(Ref. 0445)




[0403] / [0411] / [0444] / [0445]
393
3a,7a,12a,25-Tetrahydroxy-5b-cholestan-26-oic acid
 BBA0393
Mizuho Une
C27H46O6 466.651 Download ChemDraw structure file


m/z 753,709,678,619,588,529,498,439,391,367,343,253,226,199(as methyl ester-TMS derivative) (Ref. 0413)


Gastric contents from neonates with high intestinal obstruction (Ref. 0413)Patients with Zellweger syndrome: bile(Ref. 0490), urine(Ref. 0491),plasma(Ref. 0426/0490)
(Ref. 0495)



[0413] / [0426] / [0490] / [0491] / [0495]
394
3a,7a,12a-Trihydroxy-27a,27b-dihomo-5b-cholestane-26,27b-dioic acid
 BBA0394
Mizuho Une
C29H47O7 507.679 Download ChemDraw structure file

1H-NMR(CDCl3) 18-CH3=0.72, 19-CH3=0.92, 21-CH3=0.79(d,J=6.5Hz), 3b-H=4.60(tt,J=31Hz), 7b-H=4.92(q,J=9.5Hz), 12b-H=5.10(t,6Hz), 3x-OAc=2.14,2.10,2.06, 2x-COOCH3=3.675, 2x-CH2COOCH3=2.29,2.35 (Ref. 0414)
m/z 542,482,313,253 (as dimethyl ester-acetate) (Ref. 0414)m/z 752,737,662,572,482,343,253 (as dimethyl ester-TMS ether derivative) (Ref. 0414)


Patients with Zellweger syndrome: serum (Ref. 0403/0422),bile(Ref. 0403), urine(Ref. 0399/0403/0423/0425), plasma(Ref. 0426)Plasma from patients with Refsum disease(Ref. 0426)
(Ref. 0496)



[0399] / [0403] / [0414] / [0422] / [0423] / [0425] / [0426] / [0496]
395
3a,7a,12a-Trihydroxy-5a-cholest-23-en-26-oic acid
 BBA0395
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file


m/z 678,588,498,461,408,371,343,301,281,253 (as methyl ester-TMS ether derivative) (Ref. 0392)


Bile from Bufo vulgaris formosus (Ref. 0392)




[0392]
396
3a,7a,12a-Trihydroxy-5b-cholestan-26-oic acid
 BBA0396
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file

25D:180-182(Ref. 0433),183-184(Ref. 0412), 25L:195-196(Ref. 0432),195-196(Ref. 0433),199-201(Ref. 0412)
25D:[a]D=+28,25L:[a]D=+44(Ref. 0412)
25D:[a]D=+27,25L:[a]D=+43(Ref. 0433)

m/z 680,665,590,500,410,343,303,281,253 (as methyl ester-TMS ether derivative) (Ref. 0392)


Bile from Alligator mississippiensis(Ref. 0316/0400/0436), Caiman crocodilus(Ref. 0436), Crocodilus niloticus(Ref. 0436/0437), Caiman sclerops(Ref. 0438),Caiman latirostris(Ref. 0439).Bile from Varanus monitor(Ref. 0406)Bile from Xenopus mulleri(Ref. 0309), Bufo bufo vulgaris(Ref. 0309), Bufo maculatus(Ref. 0309), Bufo marinus(Ref. 0309), Bufo regularis(Ref. 0309), Aubria subsigillata(Ref. 0309), Dicroglossus occipitalis(Ref. 0309),Xenopus laevis(Ref. 0340),Bombina orientalis(Ref. 0340), Rana brevipoda(Ref. 0340), Rana limnocharis limnocharis(Ref. 0340), Bufo vulgaris formosus(Ref. 0392), Rana plancyi(Ref. 0330), Rana tigrina rugulosa(Ref. 0330), Rana nigromaculata(Ref. 0440), Rana catesbeiana(Ref. 0333/0434/0435)Zellweger syndrome : urine(Ref. 0399/0403/0404/0419/0421/0423/0425), serum(Ref. 0403/0420/0422/0423/0426), bile(Ref. 0403/0420/0423)Infantile Refsum disease:serum(Ref. 0424/0426)Duodenal fluid from intrahepatic bile duct anomalies(Ref. 0417/0418)Gastric contents from patients with intestinal obstraction(Ref. 0413)Human bile(Ref. 0408/0442)Kite bile(Ref. 0429), baboon bile(Ref. 0443)
(Ref. 0412/0432/0433/0467)



[0309] / [0316] / [0330] / [0333] / [0340] / [0392] / [0399] / [0400] / [0403] / [0404] / [0406] / [0408] / [0412] / [0413] / [0417] / [0418] / [0419] / [0420] / [0421] / [0422] / [0423] / [0424] / [0425] / [0426] / [0429] / [0432] / [0433] / [0434] / [0435] / [0436] / [0437] / [0438] / [0439] / [0440] / [0442] / [0443] / [0467]
397
7a-Hhydroxy-3-oxo-cholest-4-en-26-oic acid;7a-Hydroxy-3-oxo-4-cholesten-26-oic acid
 BBA0397
Mizuho Une
C27H42O4 430.620 Download ChemDraw structure file


m/z 516,501,426,411,395,394,269,224,209,174,162 (as methyl ester-TMS ether derivative)(Ref. 0444)


Human serum (Ref. 0444/0497/0498)




[0444] / [0497] / [0498]
398
5-Cholestene-3b,7a,12a,24-tetrol
 BBA0398
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file


m/z 632,542,499,452,409,341,319,251,145,129 (as TMS ether derivative)(Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroiddehydrogenase deficiency(Ref. 0445)




[0445]
399
5-Cholestene-3b,7a,12a,25-tetrol
 BBA0399
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file


m/z 632,542,452,411,341,251,131 (as TMS ether derivative) (Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroiddehydrogenase deficiency(Ref. 0445)




[0445]
400
3b,7a-Dihydroxy-5-cholesten-26-oic acid
 BBA0400
Mizuho Une
C27H44O4 432.636 Download ChemDraw structure file


m/z 575,500,485 (as methyl ester-TMS ether derivative) (Ref. 0444)


Human serum (Ref. 0444/0497)Plasma from 3b-hydroxy-D5-C27-steroid dehydrogenase deficiency(Ref. 0445)




[0444] / [0445] / [0497]
401
5-Cholestene-3b,7a,12a,26-tetrol
 BBA0401
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file


m/z 632,542,452,341,251,103(base peak) (as TMS ether derivative)(Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroid dehydrogenase deficiency(Ref. 0445)




[0445]
402
5-Cholestene-3b,7a,26-triol
 BBA0402
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file


m/z 634,544,454,253,233,208,129,103 (as TMS ether derivative)(Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroid dehydrogenase deficiency(Ref. 0445)




[0445]
403
27-Nor-5-cholestene-3b,7a,12a,24,25-pentol
 BBA0403
Mizuho Une
C26H44O5 436.625 Download ChemDraw structure file


m/z 706,589,499,409,341,319,251,209,129,117(as TMS ether derivative)(Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroid dehydrogenase deficiency(Ref. 0445)




[0445]
404
5-Cholestene-3b,7a,12a,24,25-pentol
 BBA0404
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file


m/z 720,630,540,131(as TMS ether derivative)(Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroid dehydrogenase deficiency(Ref. 0445)




[0445]
405
5-Cholestene-3b,7a,25,26-tetrol
 BBA0405
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file


m/z 722,632,619,529,439,349,343,253,219,129,103(as TMS ether derivative)(Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroid dehydrogenase deficiency(Ref. 0445)




[0445]
406
5-Cholestene-3b,7a,12a,25,26-pentol
 BBA0406
Mizuho Une
C27H46O5 450.651 Download ChemDraw structure file


m/z 720,707,630,617,540,527,437,347,341,251,219 (Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroid dehydrogenase deficiency(Ref. 0445)




[0445]
407
3b,7a,12a-Trihydroxy-5-cholesten-26-oic acid
 BBA0407
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file


m/z 678,588,341,251,209,129 (as methyl ester TMS ether derivative) (Ref. 0445)


Bile and urine from 3b-hydroxy-D5-C27-steroid dehydrogenase deficiency(Ref. 0445)




[0445]
408
Haemulcholic acid
3a,7a,22-Trihydroxy-5b-cholan-24-oic acid
 BBA0408
Mizuho Une
C24H40O5 408.571 Download ChemDraw structure file

22R:141-142(Ref. 0446), 22S:251-252(Ref. 0447), 247-250(Ref. 0446)
22R:[a]D=+1.0(Ref. 0446), 22S:[a]D=-10(Ref. 0447), [a]D=+2.4(Ref. 0446)
cm-1:3400, 1720(Ref. 0446/0447)
1H-NMR 22R:0.69(s,18-CH3), 0.97(s,19-CH3), 1.17(d,J=6Hz,21-CH3), 3.4-4.4(m, 3b,7b,22-H);22S:0.74(s,18-CH3), 0.96(s,19-CH3), 1.16(d,J=6Hz,21-CH3), 3.4-4.4(m, 3b,7b,22-H)(Ref. 0446)13C-NMR 22R: 43.1(C-20), 12.8(C-21), 71.2(C-22), 36.5(C-23);22S: 42.0(C-20), 12.4(C-21), 70.9(C-22), 41.5(C-23)(Ref. 0446)
m/z 623,548,533,458,443,368,353,344,295,284,269,255,254,247,227,213 (as methyl ester TMS ether derivative)(Ref. 0446)


22S-isomer: Bile from Parapristipoma trilineatum(Ref. 0447), Polypterus senegalus(Ref. 0315), Mormyrus caballus(Ref. 0315), Chrysichthys sp.(Ref. 0315), Malapterurus electricus(Ref. 0315), Schilke mystus(Ref. 0315).




[0315] / [0446] / [0447]
409
3a,7a,12a-Trihydroxy-5b-chol-22-en-24-oic acid
 BBA0409
Mizuho Une
C24H38O5 406.556 Download ChemDraw structure file

22E-isomer:181-183(methyl ester)(Ref. 0448)
cm-1:3400, 1730,1650 (methyl ester)(Ref. 0448)
methyl ester of 22E-isomer: 0.78(s,18-CH3), 0.97(s,19-CH3), 1.28(d,J=6Hz, 21-CH3), 3.65(s,COOCH3), 3.60(m, 3b-H), 3.98(m, 7b-H), 4.09(m, 12b-H), 5.82(d,J=15.3Hz, 23-H), 6.95(dd, J=15.3Hz and 7.2Hz,22-H)(Ref. 0448)
m/z 636,621,546,531,456,441,366,351,343,253,243 (as methyl ester-TMS ether derivative) (Ref. 0400/0448)


Bile from Alligator mississippiensis(Ref. 0400)




[0400] / [0448]
410
3a,7a-Dihydroxy-5b-chol-22-en-24-oic acid
 BBA0410
Mizuho Une
C24H38O4 390.556 Download ChemDraw structure file

Non-crystalline material(Ref. 0448)
cm-1:3400, 1730,1650 (methyl ester)(Ref. 0448)
methyl ester of 22E-isomer: 0.68(s,18-CH3), 0.95(s,19-CH3), 1.03(d,J=6Hz, 21-CH3), 3.65(s,COOCH3), 3.60(m, 3b-H), 3.93(m, 7b-H), 5.82(d,J=15.3Hz, 23-H), 6.89(dd, J=15.3Hz and 7.2Hz,22-H)(Ref. 0448)
m/z 458,443,368,353,255,243 (as methyl ester-TMS ether derivative) (Ref. 0400/0448)


Bile from Alligator mississippiensis(Ref. 0400)




[0400] / [0448]
411
3a,7a,12a-Trihydroxy-5a-chol-22-en-24-oic acid
 BBA0411
Mizuho Une
C24H38O5 406.556 Download ChemDraw structure file


m/z 456,366,343,259,253,243(as methyl ester-TMS ether derivative)(Ref. 0400)


Bile from Alligator mississippiensis(Ref. 0400)




[0400]
412
5a-Cholestane-3a,7a,12a,23,25-pentol
 BBA0412
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

238-239(Ref. 0449)
PMR 23S-isomer: 0.72(s,18-CH3), 0.80(s,19-CH3), 1.04(d,J=6Hz, 21-CH3), 1.23, 1.27 (26-CH3, 27-CH3), 3.97(m, 3b-H and 7b-H), 3.94(m, 12b-H), 4.01 (23-H) (Ref. 0449), 13C-NMR (Ref. 0449)
23S-isomer : m/z 667,632,577,542,487,452,433,397,362,343,307,281,253,243,131 (Ref. 0449)


Urine from patients with Cerebrotendinous xanthomatosis (Ref. 0449)




[0449]
413
12-Deoxy-5a-cyprinol
5a-Cholestane-3a,7a,26,27-tetrol
 BBA0413
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file






(Ref. 0340)



[0340]
414
5a-Cholest-25-ene-3a,7a,12a,26-tetrol
 BBA0414
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

221-224(Ref. 0311)
cm- 13340,890(Ref. 0311)
PMR 0.81(s,18-CH3), 0.91(s,19-CH3), 1.20(d,J=6Hz, 21-CH3), 4.09 (m, 3b-H), 4.24(7b-H and 12b-H), 4.35 (s, 26-CH2-OH), 4.94, 5.41(s, 27=CH2) (Ref. 0311)




(Ref. 0311)



[0311]
415
5a-Cholest-25-ene-3a,7a,12a-triol
 BBA0415
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

215(Ref. 0337)





(Ref. 0337)



[0337]
416
5a-Cholestane-3a,7a,25-triol
 BBA0416
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

197-198(Ref. 0451)
cm-1 3333,1230,1158,1095,1078,1063,1034,1020,1005,957,904(Ref. 0451)

m/z 402,384,369,366,351,289,273,271,264,255,253,249,246,231(Ref. 0451)



(Ref. 0451)



[0451]
417
5b-Cholestane-3a,7a,12a,22,26-pentol
 BBA0417
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

22S-isome: 137-139, 22R-isome: non-crystalline material (Ref. 0398)
cm-1 3400(Ref. 0398)
PMR 0.92(s,18-CH3), 1.04(s,19-CH3), 1.15(d,J=6Hz, 27-CH3), 1.45(d,J=6Hz, 21-CH3), 3.65-4.43(m, 3b-H, 7b-H, 12b-H, 22-H, and 26-CH2) (Ref. 0398)




(Ref. 0398)



[0398]
418
5b-Cholestane-3a,7a,12a,23,26-pentol
 BBA0418
Mizuho Une
C27H48O5 452.667 Download ChemDraw structure file

23R-isomer: non-crystalline material, 23S-isomer: 213-215(Ref. 0398)
cm-1 3400(Ref. 0398)
PMR 23R-isomer: 0.87(s,18-CH3), 1.01(s,19-CH3), 1.15(d,J=6Hz, 27-CH3), 1.36(d,J=6Hz, 21-CH3), 3.69-4.36(m, 3b-H, 7b-H, 12b-H, 23-H, and 26-CH2)(Ref. 0398); 0.88(s,18-CH3), 1.02(s,19-CH3), 1.24(d,J=6Hz, 27-CH3), 1.43(d,J=6Hz, 21-CH3), 3.70-4.35(m, 3b-H, 7b-H, 12b-H, 23-H, and 26-CH2)(Ref. 0398)
m/z 542,452,363,343,253,247,157(as TMS ether)(Ref. 0398)



(Ref. 0398)



[0398]
419
5b-Cholestane-3a,7a,12a,22-tetrol
 BBA0419
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

22R-isomer: 127-128.5, 22S-isomer: 203-204(Ref. 0369)
22R-isomer: [a]D=+34, 22S-isomer: [a]D=+20(Ref. 0369)
cm-1 3400,1080,1040,1020,980,950,915(Ref. 0369)
PMR 22R-isomer: 0.87(s,18-CH3), 1.02(s,19-CH3), 1.46(d,J=6Hz, 21-CH3), 0.86,0.89(d,J=6Hz, 26- and 27-CH3), 3.70(m, 3b-H), 4.08(m, 7b-H), 4.28(m, 12b-H), 3.94(m, 22-H), 22S-isomer: 0.92(s,18-CH3), 1.04(s,19-CH3), 1.46(d,J=6Hz, 21-CH3), 0.89(d,J=6Hz, 26- and 27-CH3), 3.66(m, 3b-H), 4.06(m, 7b-H), 4.30(m, 12b-H), 3.93(m, 22-H).(Ref. 0369)
m/z 724,653,634,563.544,473,454,383,364,293,253,173(as TMS ether)(Ref. 0369)



(Ref. 0369)



[0369]
420
3a,7a,12a-Trihydroxy-5b-cholestan-23-one
 BBA0420
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

173-174(Ref. 0369)
cm-1 3400,1710,1080,1040,980,950,915(Ref. 0369)





(Ref. 0369)



[0369]
421
5b-Cholest-25-ene-3a,7a,12a,23-tetrol
 BBA0421
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

23R-isomer: non-crystalline, 23S-isomer: 194.5-195(Ref. 0452)
23R-isome: [a]D=+40.3, 23S-isomer: [a]D=+44.2(Ref. 0452)
cm-1 3400,890(Ref. 0452)
23R-isomer: 0.87(s,18-CH3), 1.01(s,19-CH3), 1.37(d,J=6Hz, 21-CH3), 1.83(s,27-CH3), 3.5-4.4(m, 3b-H, 7b-H, 12b-H, 23-H), 4.98(s,26-CH2), 23S-isomer: 0.88(s,18-CH3), 1.01(s,19-CH3), 1.41(d,J=6Hz, 21-CH3), 1.89(s,27-CH3), 3.5-4.4(m, 3b-H, 7b-H, 12b-H, 23-H), 4.98(s,26-CH2)(Ref. 0452)
m/z 667,577,487,397,307,343,253 (as TMS-ether)(Ref. 0452)



(Ref. 0452)



[0452]
422
3a,7a,12a-Trihydroxy-5b-cholestan-24-one
 BBA0422
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

141-142(Ref. 0372)





(Ref. 0372)



[0372]
423
5b-Cholest-25-ene-3a,7a,12a,24-tetrol
 BBA0423
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

24R-isomer: 168.5-170, 24S-isomer: 190-190.5(Ref. 0367)
24R-isomer: 0.84(s,18-CH3), 1.01(s,19-CH3), 1.26(d,J=6Hz, 21-CH3), 1.88(s,27-CH3), 3.4-4.5(m, 3b-H, 7b-H, 12b-H, 24-H), 4.98,5.20(s,26-CH2), 24S-isomer: 0.83(s,18-CH3), 1.01(s,19-CH3), 1.26(d,J=6Hz, 21-CH3), 1.88(s, 27-CH3), 3.4-4.5(m, 3b-H, 7b-H, 12b-H, 24-H), 4.94,5.18(s,26-CH2)(Ref. 0367)




(Ref. 0367)



[0367]
424
5b-Cholestane-3a,7b,12a,25-tetrol
 BBA0424
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

160-161.5(Ref. 0327)
cm-1 3350(Ref. 0327)
PMR: 0.82(s,18-CH3), 0.99(s,19-CH3), 1.20(d,J=6Hz, 21-CH3), 1.34(s,26-and27-CH3), 3.72(m, 3b-H and 7a-H), 4.13(s, 12b-H)(Ref. 0327)




(Ref. 0327)



[0327]
425
3a,7a,12a-Trihydroxy-5b-cholestan-26-al
 BBA0425
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

non-crystalline (Ref. 0453/0454)
cm-1 3400,1710(Ref. 0453)

m/z 434,416,402,398,384,380,365,289,271,253,227,211(Ref. 0454), m/z 545,470,455,380,365,343,253, 226, 211 (as TMS ether)(Ref. 0454)



(Ref. 0453/0454)



[0453] / [0454]
426
7a,12a,26-Trihydroxy-5b-cholestan-3-one
 BBA0426
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file


m/z 650,635,560,545,470,455,347,269,251(as TMS ether)(Ref. 0454)



(Ref. 0454)



[0454]
427
7a,12a-Dihydroxy-3-oxo-5b-cholestan-26-al
 BBA0427
Mizuho Une
C27H44O4 432.636 Download ChemDraw structure file


m/z 432,414,399,396,381,287,273,269,251(as TMS ether)(Ref. 0454)



(Ref. 0454)



[0454]
428
5b-Cholestane-3b,7a,25-triol
 BBA0428
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

157-160(Ref. 0455)

m/z 402,387,384,369,366,351,289,273,271,255,253(Ref. 0455)



(Ref. 0455)



[0455]
429
5b-Cholestane-3b,7a,12a,25-tetrol
 BBA0429
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file


m/z 436,418,400,382,364,271,253(Ref. 0455)



(Ref. 0455)



[0455]
430
7a,12a,25-Trihydroxy-5b-cholestan-3-one
 BBA0430
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

198-199.5(Ref. 0456)
cm-1 3426,1701,1148,1095,1078,1040,979,937(Ref. 0456)





(Ref. 0456)



[0456]
431
7a,12a,25-Trihydroxycholest-4-en-3-one
 BBA0431
Mizuho Une
C27H44O4 432.636 Download ChemDraw structure file

222-223(Ref. 0456)
l243nm e=14.834(Ref. 0456)
cm-1 3367,1672,1639,1230,1190,1160,1086,1047,1007,954,919,862(Ref. 0456)

m/z 432,414,396,378,376,358,315,267,261,124(Ref. 0456)



(Ref. 0456)



[0456]
432
7a,25-Dihydroxy-5b-cholestan-3-one
 BBA0432
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

180-181(Ref. 0456)
cm-1 3484,3412,1709,1098,1077,1037,1007,980 (Ref. 0456)
PMR 0.71(s,18-CH3), 0.97(d,J=6Hz, 21-CH3), 1.01(s,19-CH3), 1.23 (s,26-and27-CH3), 3.98(m, 7b-H)(Ref. 0456)




(Ref. 0456)



[0456]
433
7a,25-Dihydroxycholest-4-en-3-one
 BBA0433
Mizuho Une
C27H44O3 416.636 Download ChemDraw structure file

205-206(Ref. 0456)
l243nm e=16.470(Ref. 0456)
cm-1 3333,1661,1618,1234,1193,1156,1149,1044,1030,952,940,913(Ref. 0456)
PMR 0.71(s,18-CH3), 0.93(d,J=6Hz, 21-CH3), 1.19(s,19-CH3, 26-and27-CH3), 3.9(m, 7b-H),5.75(4-H)(Ref. 0456)
m/z 416,398,380,342,269,267,124(Ref. 0456)



(Ref. 0456)



[0456]
434
5b-Cholest-25-ene-3a,7a,12a,26-tetrol
 BBA0434
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

not isolated as crystalline(Ref. 0310)





(Ref. 0310)



[0310]
435
5b-Cholestane-3a,7a-diol
 BBA0435
Mizuho Une
C27H48O2 404.669 Download ChemDraw structure file

84-86(Ref. 0457)
[a]D=+14.1(Ref. 0457)





(Ref. 0457)



[0457]
436
5b-Cholestane-3a-ol
 BBA0436
Mizuho Une
C27H48O1 388.669 Download ChemDraw structure file

116-118(Ref. 0457)
[a]D=+30.7(Ref. 0457)





(Ref. 0457)



[0457]
437
5b-Cholestane-3a,12a-diol
 BBA0437
Mizuho Une
C27H48O2 404.669 Download ChemDraw structure file

108-110(Ref. 0457)
[a]D=+45.0(Ref. 0457)





(Ref. 0457)



[0457]
438
7a-Hydroxy-5b-cholestan-3-one
 BBA0438
Mizuho Une
C27H46O2 402.653 Download ChemDraw structure file

120-121(Ref. 0458)





(Ref. 0458)



[0458]
439
7a,12a-Dihydroxy-5b-cholestan-3-one
 BBA0439
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

209-210(Ref. 0459)
[a]D=+42.6(Ref. 0459)





(Ref. 0459)



[0459]
440
7a,12a-Dihydroxycholest-4-en-3-one
 BBA0440
Mizuho Une
C27H44O3 416.636 Download ChemDraw structure file

228-229(Ref. 0459)
[a]D=+85.0(Ref. 0459)
l243nm e=16.800(Ref. 0459)





(Ref. 0459)



[0459]
441
5b-cholest-24-ene-3a,7a-diol
 BBA0441
Mizuho Une
C27H46O2 402.653 Download ChemDraw structure file

67-69(as diacetate)(Ref. 0363/0460)
cm-1 826(Ref. 0363/0460)





(Ref. 0363/0460)



[0363] / [0460]
442
5b-cholest-25-ene-3a,7a-diol
 BBA0442
Mizuho Une
C27H46O2 402.653 Download ChemDraw structure file

69-72(as diacetate)(Ref. 0363/0460)
cm-1 890(Ref. 0363/0460)





(Ref. 0363/0460)



[0363] / [0460]
443
5b-Cholestane-3a,7a,24,25-tetrol
 BBA0443
Mizuho Une
C27H48O4 436.668 Download ChemDraw structure file

24R-isomer: 201-203; 24S-isomer: 203-204(Ref. 0460)
24R-isomer: [a]D=+17.8, 24S-isomer: [a]D=+3.0(Ref. 0460)
cm-1 24R-isomer:3385,1460,1442,1371,1164,1155,1122,1106,1067,1054,1023,992,970,906,890; 24S-isomer: 3290,1455,1365,1155,1118,1104,1067,1036,990,967,902,890. (Ref. 0460)
24R-isomer: 0.68(s,18-CH3), 0.91(s,19-CH3), 0.94(d,J=7Hz, 21-CH3), 1.23, 1.26 (s,26-and27-CH3); 24S-isomer: 0.66(s,18-CH3), 0.91(s,19-CH3), 0.94(d,J=7Hz, 21-CH3), 1.23, 1.26 (s,26-and27-CH3) (Ref. 0460)
m/z 709,634,593,529,503,413,323,283,255,131(as TMS ether) (Ref. 0460)



(Ref. 0460)



[0460]
444
5b-Cholestane-3a,24,25-triol
 BBA0444
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

24R-isomer:148-150, 24S-isomer: 162-164(Ref. 0460)
24R-isomer: [a]D=+40.0, 24S-isomer:[a]D=+17.3(Ref. 0460)
24R-isomer: 3300,1455,1445,1370,1140,1075,1028,980,956,945,936,918,898; 24S-isomer: 3320, 1457,1445,1372,1150,1033,960,920(Ref. 0460)
24R-isomer: 0.65(s,18-CH3), 0.92(s,19-CH3), 0.92(d,J=7Hz, 21-CH3), 1.14, 1.18 (s,26-and27-CH3); 24S-isomer: 0.64(s,18-CH3), 0.92(s,19-CH3), 0.94(d,J=7Hz, 21-CH3), 1.17, 1.22 (s,26-and27-CH3) (Ref. 0460)
m/z 636,621,531,505,456,441,415,351,345,325,257,255,215,131(as TMS ether) (Ref. 0460)



(Ref. 0460)



[0460]
445
5b-Cholest-24-en-3a-ol
 BBA0445
Mizuho Une
C27H46O1 386.654 Download ChemDraw structure file

non-crystalline(Ref. 0460)
cm-1 1736,1660,1460,1445,1375,1360,1245,1025,825(as acetate)(Ref. 0460)





(Ref. 0460)



[0460]
446
5b-Cholest-25-en-3a-ol
 BBA0446
Mizuho Une
C27H46O1 386.654 Download ChemDraw structure file

non-crystalline(Ref. 0460)
cm-1 1728,1650,1465,1450,1370,1350,1255,1025,950,930,890(as acetate)(Ref. 0460)





(Ref. 0460)



[0460]
447
5b-Cholestane-3a,26-diol
 BBA0447
Mizuho Une
C27H48O2 404.669 Download ChemDraw structure file

150-155(Ref. 0461)
cm-1 3300(Ref. 0460)





(Ref. 0460)



[0460] / [0461]
448
3a-Hydroxy-5b-cholestan-26-al
 BBA0448
Mizuho Une
C27H46O2 402.653 Download ChemDraw structure file

non-crystalline(Ref. 0461)
cm-1 3400, 1720(Ref. 0461)





(Ref. 0461)



[0461]
449
7a-Hydroxycholest-4-en-3-one
 BBA0449
Mizuho Une
C27H44O2 400.637 Download ChemDraw structure file

183-184(Ref. 0462)
[a]D=+67(Ref. 0462)
l242.5nm e=16.100(Ref. 0462)





(Ref. 0462)



[0462]
450
12a-Hydroxycholest-4-en-3-one
 BBA0450
Mizuho Une
C27H44O2 400.637 Download ChemDraw structure file

142-143(Ref. 0463)
[a]D=+86(Ref. 0463)
l241nm e=17.500(Ref. 0463)





(Ref. 0463)



[0463]
451
12a-Hydroxy-5b-cholestan-3-one
 BBA0451
Mizuho Une
C27H46O2 402.653 Download ChemDraw structure file

122(Ref. 0463)
[a]D=+51<0463>>





(Ref. 0463)



[0463]
452
7b-Hydroxycholest-4-en-3-one
 BBA0452
Mizuho Une
C27H44O2 400.637 Download ChemDraw structure file

182-183(Ref. 0462)
[a]D=+62(Ref. 0462)





(Ref. 0462)



[0462]
453
5b-Chelest-24-ene-3a,7a,12a-triol
 BBA0453
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

171(Ref. 0339)
cm-1 3650,1645(Ref. 0339)





(Ref. 0339)



[0339]
454
3a,6a,7a,12a-Tetrahydroxy-5b-cholest-24-en-26-oic acid
 BBA0454
Mizuho Une
C27H44O6 464.635 Download ChemDraw structure file

non-crystalline(Ref. 0415)
PMR: 0.80(s,18-CH3), 1.04(s,19-CH3), 1.24(d,J=7Hz, 21-CH3), 1.90(s,27-CH3), 3.68-3.82(m,3b-H), 4.20-4.30(m, 6b-H,7b-H,12b-H), 6.94(t,J=9Hz,24-H)(Ref. 0415)




(Ref. 0415)



[0415]
455
3a,7a-Dihydroxy-12-oxo-5a-cholestan-26-oic acid
 BBA0455
Mizuho Une
C27H44O5 448.635 Download ChemDraw structure file

138-139(methyl ester-diacetate)(Ref. 0427)
[a]D=+60(methyl ester-diacetate)(Ref. 0427)
cm-1 1727,1700,1243,1089,1030,1022,963,936,873,849 (methyl ester-diacetate)(Ref. 0427)

m/z 349,289(Ref. 0427)



(Ref. 0427)



[0427]
456
3a,7a-Dihydroxy-5a-cholestan-26-oic acid
 BBA0456
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

248-250(Ref. 0427/0464)
[a]D=0(Ref. 0464)
cm-1 3389,3305,1706,1302,1262,1234,1209,1090,1069,1042,1033,1000,961,888(Ref. 0427)

m/z 448,430,412,399,273,255,249,231,213 (as methyl ester)(Ref. 0427)



(Ref. 0427/0464/0465)



[0427] / [0464] / [0465]
457
3b,7a-Dihydroxy-5a-cholestan-26-oic acid
 BBA0457
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

251-253(Ref. 0464)
cm-1 3400,3252,1712,1229,1155,1087,1033,1028,943(Ref. 0464)





(Ref. 0464)



[0464]
458
3-Oxo-7a-hydroxy-5a-cholestan-26-oic acid
 BBA0458
Mizuho Une
C27H44O4 432.636 Download ChemDraw structure file

211-213(as acetate)(Ref. 0464)
cm-1 1731,1695,1250,1157,1022,938(Ref. 0464)





(Ref. 0464)



[0464]
459
3,7,12-Trioxo-24-homo-5a-cholan-25-oic acid
 BBA0459
Mizuho Une
C25H36O5 416.550 Download ChemDraw structure file

206-211(Ref. 0358)





(Ref. 0358)



[0358]
460
3a,7a-Dihydroxy-24-homo-5a-cholan-25-oic acid
 BBA0460
Mizuho Une
C25H42O4 406.599 Download ChemDraw structure file

122(as methyl ester)(Ref. 0451)
cm-1 3367,1748,1270,1239,1209,1169,1034,1005,961,887(as methyl ester)(Ref. 0451)

m/z 564,549,474,459,384,369,345,255,243,228,213(as methyl ester-TMS ether)(Ref. 0451)



(Ref. 0451)



[0451]
461
3,7-Dioxo-24-homo-5a-cholan-25-oic acid
 BBA0461
Mizuho Une
C25H38O4 402.567 Download ChemDraw structure file

188-189(as methyl ester)(Ref. 0451)





(Ref. 0451)



[0451]
462
3,7-Dioxo-5a-cholestan-26-oic acid
 BBA0462
Mizuho Une
C27H42O4 430.620 Download ChemDraw structure file

124-125(as methyl ester)(Ref. 0465)
cm-1 2940,2860,1739,1723,1708,1164(as methyl ester)(Ref. 0465)
PMR: 0.67(s,18-CH3), 0.90(d,J=6Hz, 21-CH3),1.14(d,J=7Hz, 27-CH3), 1.25(s,19-CH3), 3.67(s, COOCH3)(Ref. 0465)
m/z 444,426,412,384,287,269,260,247,246,245(as methyl ester)(Ref. 0465)



(Ref. 0465)



[0465]
463
5a-Cholestane-3a,7a,12a-triol
 BBA0463
Mizuho Une
C27H48O3 420.668 Download ChemDraw structure file

251(Ref. 0466)





(Ref. 0466)



[0466]
464
7a,12a-Dihydroxy-5a-Cholestan-3-one
 BBA0464
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

190-192(Ref. 0466)





(Ref. 0466)



[0466]
465
3a,12a-Dihydroxy-5b-cholestan-7-one
 BBA0465
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

140(Ref. 0467)
PMR: 0.68(s,18-CH3), 0.86(d,J=6Hz, 26- and 27-CH3), 0.96(d,J=6Hz, 21-CH3), 1.17(s,19-CH3), 3.54(m,3b-H), 4.02(m, 12b-H)(Ref. 0467)




(Ref. 0467)



[0467]
466
Cholest-4-ene-3a,7a,12a-triol
 BBA0466
Mizuho Une
C27H46O3 418.652 Download ChemDraw structure file

208-210(Ref. 0466)





(Ref. 0466)



[0466]
467
24-Nor-5b-cholestane-3a,7a,12a,23,25-pentol
 BBA0467
Mizuho Une
C26H46O5 438.640 Download ChemDraw structure file

172-175(Ref. 0383)
cm-1 3390 (KBr disc)
PMR: 0.68(s,18-CH3), 0.84(s,19-CH3), 0.99(d,J=6Hz, 21-CH3), 1.04,1.08 (s, 26-and 27-CH3)(Ref. 0383)
m/z 667,618,577,529,487,439,397,349,307(as TMS ether)(Ref. 0383)



(Ref. 0383)



[0383]
468
24-Nor-5b-cholestane-3a,7a,12a,23-tetrol
 BBA0468
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

23S-isomer:115-118, 23R-isomer:246-247(Ref. 0468)
23S-isomer: [a]D=+26.67, 23R-isomer: [a]D=+43.34(Ref. 0468)





(Ref. 0468)



[0468]
469
24-Nor-5b-cholestane-3a,7a,12a,26-tetrol
 BBA0469
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

25S-isomer: 178-181, 25R-isomer: 59-61(Ref. 0468)
25S-isomer: [a]D=+29.0, 25R-isomer: [a]D=+40.0(Ref. 0468)





(Ref. 0468)



[0468]
470
(22R)-24-Nor-5b-cholestane-3a,7a,22,25-tetrol
 BBA0470
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

193(Ref. 0447)





(Ref. 0447)



[0447]
471
24-Nor-5b-cholestane-3a,7a,23,25-tetrol
 BBA0471
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

23b-isomer: 189.5-190.5, 23a-isomer: 182.5-183(Ref. 0469)
23b-isomer: [a]D=+30, 23a-isomer: [a]D=-9 (Ref. 0469)
cm-1 23b-isomer: 3420,2930,1460,1370,1070,993,972,893,850; 23a-isomer: 3400,2930, 1458, 1370,1070,992,970,891,848 (Ref. 0469)

m/z 23b-isomer: 579,530,489,440,399,384,309,253,243,131; 23a-isomer: 579,489,440,399, 384,309,253,243,131 (Ref. 0469)



(Ref. 0469)



[0469]
472
24-Nor-5b-cholestane-3a,7a,25,26-tetrol
 BBA0472
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

182.5-183(Ref. 0469)
cm-1 3400,2930,2865,1456,1380,1073,975 (KBr disc)(Ref. 0469)

m/z 710,607,517,427,350,337,255,253,243,219,173(Ref. 0469)



(Ref. 0469)



[0469]
473
24-Nor-5b-cholestane-3a,7a,12a-triol
 BBA0473
Mizuho Une
C26H46O3 406.642 Download ChemDraw structure file

182-184(Ref. 0468/0383)
[a]D=+31.23(Ref. 0468)
cm-1 3370,1360-1380 (KBr disc)(Ref. 0383)
PMR: 0.64(s,18-CH3), 0.84(s,19-CH3), 0.96(d,J=6Hz, 21-CH3), 0.84,0.92 (s, 26-and 27-CH3)(Ref. 0383)
m/z 622,546,532,461,456,442,433,371,352,343,281(Ref. 0383)



(Ref. 0383/0468)



[0383] / [0468]
474
24-Nor-5b-cholest-23-ene-3a,7a,12a-triol
 BBA0474
Mizuho Une
C26H44O3 404.626 Download ChemDraw structure file

190-191(Ref. 0383)
cm-1 3375,1365-1395 (KBr disc)(Ref. 0383)
PMR: 0.68(s,18-CH3), 0.88(s,19-CH3), 0.94(d,J=6Hz, 21-CH3), 1.60,1.68 (s, 26-and 27-CH3)(Ref. 0383)
m/z 564,530,481,474,461,440,391,384,371,350,344,301,294,254,253,211(Ref. 0383)



(Ref. 0383/0468)



[0383] / [0468]
475
24-Nor-5b-cholest-25-ene-3a,7a,12a-triol
 BBA0475
Mizuho Une
C26H44O3 404.626 Download ChemDraw structure file

166-169(Ref. 0383)
cm-1 3375,883 (KBr disc)(Ref. 0383)

m/z 620,530,461,440,391,371,350,301,281,211 (as TMS derivative) (Ref. 0383)



(Ref. 0383/0468)



[0383] / [0468]
476
24-Nor-5b-cholestane-3a,7b,25-triol
 BBA0476
Mizuho Une
C26H46O3 406.642 Download ChemDraw structure file

154-155(Ref. 0308)
0.74(s,3H,18-CH3), 0.98(s,3H,19-CH3), 1.05(d, J=6Hz, 3H,21-CH3), 1.43(s,6H,26-and 27-CH3), 3.60-4.00(m,2H,3b-H and 7a-H (pyridine-d5)(Ref. 0408)




(Ref. 0408)



[0308] / [0408]
477
27-Nor-5b-cholestane-3a,7a,12a,26-tetrol
 BBA0477
Mizuho Une
C26H46O4 422.641 Download ChemDraw structure file

202(Ref. 0328)





(Ref. 0328)



[0328]
478
3a,7a,12a-Trihydroxy-27-nor-5b-cholestan-25-one
 BBA0478
Mizuho Une
C26H44O4 420.625 Download ChemDraw structure file

162(Ref. 0338)


C 73.89, H 10.40 (Calcd C 74.24, H 10.54) (Ref. 0338)


(Ref. 0338)



[0338]
479
27-Nor-5b-cholestane-3a,7a,12a-triol
 BBA0479
Mizuho Une
C26H46O3 406.642 Download ChemDraw structure file

187.5-189(Ref. 0470)





(Ref. 0470)



[0470]
480
27-Nor-5b-cholest-24-ene-3a,7a,12a-triol
 BBA0480
Mizuho Une
C26H44O3 404.626 Download ChemDraw structure file

182(Ref. 0351)
cm-1 3400 (KBr disc)(Ref. 0351)
0.81(s,3H,18-CH3), 0.99(s,3H,19-CH3), 1.21(d, J=6Hz, 3H,21-CH3), 1.62(s,3H,26-CH3), 3.45-4.40(m,3H,3b-, 7b- and 12b-H), 5.46(2H, m, -CH=CH-) (pyridine-d5)(Ref. 0351)




(Ref. 0351)



[0351]
481
26,27-Dinor-5a-cholestane-3a,7a,12a,24-tetrol
 BBA0481
Mizuho Une
C25H44O4 408.614 Download ChemDraw structure file





Rana pipiens (Ref. 0309)




[0309]
482
26,27-Dinor-5b-cholestane-3a,7a,12a,25-tetrol
 BBA0482
Mizuho Une
C25H44O4 408.614 Download ChemDraw structure file

202(Ref. 0328)





(Ref. 0328)



[0328]
483
26,27-Dinor-5b-cholestane-3a,7a,12a-triol
 BBA0483
Mizuho Une
C25H44O3 392.615 Download ChemDraw structure file

185-186(Ref. 0336)





(Ref. 0336)



[0336]
484
3a,7a,12a-Trihydroxy-5a-cholan-24-al
 BBA0484
Mizuho Une
C24H40O4 392.572 Download ChemDraw structure file

CHCl3 as triacetate: 2720,1735,1725,1250,1050 cm-1 (Ref. 0333)





(Ref. 0333)



[0333]
485
3a,7a,12a-Trihydroxy-5b-cholan-24-al
 BBA0485
Mizuho Une
C24H40O4 392.572 Download ChemDraw structure file

150(Ref. 0304)
2820, 2720, 1725 cm-1 (Ref. 0304)
0.67(s,3H,18-CH3), 0.83(s,3H,19-CH3), 0.84(d, J=6Hz, 3H,21-CH3), 1.97(s,6H, 2x-OCOCH3), 2.03(s,3H, -OCOCH3), 4.70(m,1H,3b-H), 5.05(m,1H,7b-H), 5.23(m,1H,12b-H), 9.83(t, 1H,J=3Hz,-CHO) (pyridine-d5)(Ref. 0407)




(Ref. 0304/0392/0467)



[0304] / [0392] / [0407] / [0467]
486
5b-Cholane-3a,6a,24-triol
 BBA0486
Mizuho Une
C24H42O3 378.588 Download ChemDraw structure file

150-155(Ref. 0471)
0.69(s,3H,18-CH3), 0.93(s,3H,19-CH3), 0.95(d, J=6.6Hz, 3H,21-CH3), 3.50(m,3H, 3b- and 24-CH2), 4.00(m,1H,6b-H), (CHCl3)(Ref. 0471)




(Ref. 0471)



[0471]
487
5b-Cholane-3a,7a,12a-triol
 BBA0487
Mizuho Une
C24H42O3 378.588 Download ChemDraw structure file

186-188(Ref. 0336)





(Ref. 0336)



[0336]
488
5b-Cholane-3a,7a,24-triol
 BBA0488
Mizuho Une
C24H42O3 378.588 Download ChemDraw structure file

99-100(Ref. 0472)
0.69(s,3H,18-CH3), 0.93(s,3H,19-CH3), 0.97(d, J=6.6Hz, 3H,21-CH3), 3.38(m,1H, 3b-H), 3.51(m,2H,24-CH2), 3.79(m,1H,7b-H), (CD3OD)(Ref. 0472)




(Ref. 0472)



[0472]
489
5b-Cholane-3a,7b,24-triol
 BBA0489
Mizuho Une
C24H42O3 378.588 Download ChemDraw structure file

163-164(Ref. 0472)
KBr disc 3400 cm-1 (Ref. 0472)
0.71(s,3H,18-CH3), 0.96(s,3H,19-CH3), 0.97(d, J=6.6Hz, 3H,21-CH3), 3.50(m, 4H, 3b-H, 7b-H, and 24-CH2)(CD3OD)(Ref. 0472)




(Ref. 0472)



[0472]
490
5b-Cholane-3a,12a,24-triol
 BBA0490
Mizuho Une
C24H42O3 378.588 Download ChemDraw structure file

118-120(Ref. 0471)
0.71(s,3H,18-CH3), 0.93(s,3H,19-CH3), 1.01(d, J=6.4Hz, 3H,21-CH3), 3.51(m,3H, 3b-H and 24-CH2), 3.96(m,1H,12b-H), (CD3OD)(Ref. 0471)




(Ref. 0471/0473)



[0471] / [0473]
491
3a,7a-Dihydroxy-5b-cholan-24-al
 BBA0491
Mizuho Une
C24H40O3 376.573 Download ChemDraw structure file

2720, 1720 cm-1 (Ref. 0405)





(Ref. 0405)



[0405]
492
24-Nor-5b-cholane-3a,7a,12a,22,23-pentol
 BBA0492
Mizuho Une
C23H40O5 396.561 Download ChemDraw structure file

202(Ref. 0310)
3400, 1075, 1020, 990, 920, 894(Ref. 0310)





(Ref. 0310)



[0310]
493
3a,7a,12a-Trihydroxy-24-nor-5b-cholan-23-al
 BBA0493
Mizuho Une
C23H38O4 378.545 Download ChemDraw structure file

80-85(as triacetate)(Ref. 0474)
3400, 1740 cm-1 (Ref. 0452)
0.81(s,3H,18-CH3), 1.00(s,3H,19-CH3), 1.23(d, J=6Hz, 3H,21-CH3), 3.70(m,1H,3b-H), 4.09(m,1H,7b-H), 4.19(m,1H,12b-H), 9.83(t, 1H,J=3Hz,-CHO) (pyridine-d5)(Ref. 0452)
m/z 504,460,444,401,400,384,340,324,313,280,253 (Ref. 0474)



(Ref. 0452/0474)



[0452] / [0474]
494
24-Nor-5b-cholane-3a,7a,12a,23-tetrol
 BBA0494
Mizuho Une
C23H40O4 380.561 Download ChemDraw structure file

215-220<0471>>
0.72(s,3H,18-CH3), 0.92(s,3H,19-CH3), 1.02(d, J=6.6Hz, 3H,21-CH3), 3.36(m,1H, 3b-H), 3.55 and 3.63(m, 2H, 23-CH2), 3.79(m,1H,7b-H), 3.95(m,1H,12b-H) (CD3OD)(Ref. 0471)




(Ref. 0471)



[0471]
495
24-Nor-5b-cholane-3a,7a,22,23-tetrol
 BBA0495
Mizuho Une
C23H40O4 380.561 Download ChemDraw structure file

22S: 138.5-140, 22R: 229-230 (Ref. 0446)
22S: [a]D=+8.2, 22R: [a]D=+0.7 (Ref. 0446)
3400 cm-1 (KBr disc) (Ref. 0446)
22S: 0.71(s,3H,18-CH3), 0.97(s,3H,19-CH3), 1.24(d, J=6Hz, 3H,21-CH3), 3.4-4.4(m,5H, CH-OH's); 22R:0.77(s,3H,18-CH3), 0.97(s,3H,19-CH3), 1.21(d, J=6Hz, 3H,21-CH3), 3.4-4.4(m,5H, CH-OH's)(Ref. 0446)
m/z 565,475,385,345,295,255 (as TMS derivative) (Ref. 0446)



(Ref. 0446)



[0446]
496
24-Nor-5b-cholane-3a,7b,22,23-tetrol
 BBA0496
Mizuho Une
C23H40O4 380.561 Download ChemDraw structure file

208-210(Ref. 0448)
3400cm-1 (KBr disc) (Ref. 0448)
0.71(s,3H,18-CH3), 0.95(s,3H,19-CH3), 1.15(d, J=6Hz, 3H,21-CH3), 3.4-4.3(m,5H, CH-OH's)(Ref. 0448)




(Ref. 0448)



[0448]
497
24-Nor-5b-cholane-3a,12a,22,23-tetrol
 BBA0497
Mizuho Une
C23H40O4 380.561 Download ChemDraw structure file

120-122 (Ref. 0446)
3400cm-1 (KBr disc) (Ref. 0446)
0.78(s,3H,18-CH3), 0.93(s,3H,19-CH3), 1.34(d, J=6Hz, 3H,21-CH3), 3.4-4.3(m,5H, CH-OH's)(Ref. 0446)




(Ref. 0446)



[0446]
498
24-Nor-5b-cholane-3a,6a,23-triol
 BBA0498
Mizuho Une
C23H40O3 364.562 Download ChemDraw structure file

212-215 (Ref. 0471)
0.70(s,3H,18-CH3), 0.93(s,3H,19-CH3), 0.96(d, J=6.6Hz, 3H,21-CH3), 3.51-3.61(m,3H, 3b-H, 23-H), 4.00(m,1H,6b-H)(Ref. 0471)




(Ref. 0471)



[0471]
499
24-Nor-5b-cholane-3a,7a,12a-triol
 BBA0499
Mizuho Une
C23H40O3 364.562 Download ChemDraw structure file

200-202(Ref. 0475)





(Ref. 0475)



[0475]
500
24-Nor-5b-cholane-3a,7a,23-triol
 BBA0500
Mizuho Une
C23H40O3 364.562 Download ChemDraw structure file

247-249 (Ref. 0471)
0.70(s,3H,18-CH3), 0.93(s,3H,19-CH3), 0.96(d, J=6.6Hz, 3H,21-CH3), 3.35(m,1H, 3b-H), 3.54 and 3.61(m, each 1H, 23-H), 3.79(m,1H,7b-H)(Ref. 0471)




(Ref. 0471)



[0471]
501
24-Nor-5b-cholane-3a,7b,23-triol
 BBA0501
Mizuho Une
C23H40O3 364.562 Download ChemDraw structure file

179-181(Ref. 0471)
0.72(s,3H,18-CH3), 0.96(s,3H,19-CH3), 0.96(d, J=6.6Hz, 3H,21-CH3), 3.48(m,2H, 3b-H and 7a-H), 3.54 and 3.61(m, each 1H, 23-H)(CD3OD)(Ref. 0471)




(Ref. 0471)



[0471]
502
24-Nor-5b-cholane-3a,12a,23-triol
 BBA0502
Mizuho Une
C23H40O3 364.562 Download ChemDraw structure file

210-212(Ref. 0471)
0.72(s,3H,18-CH3), 0.93(s,3H,19-CH3), 1.01(d, J=6.6Hz, 3H,21-CH3), 3.54(m,2H, 3b-H and 23-H), 3.61(m, 1H, 23-H), 3.96(m,1H,12b-H)(CD3OD)(Ref. 0471)




(Ref. 0471)



[0471]
503
24-Nor-5b-chol-22-ene-3a,7a,12a-triol
 BBA0503
Mizuho Une
C23H38O3 362.546 Download ChemDraw structure file

183-184(Ref. 0368)
3400,1660,1075,1020,990,920,910,894,890 cm-1 (Ref. 0368)
0.85(s,3H,18-CH3), 1.00(s,3H,19-CH3), 1.33(d, J=6Hz, 3H,21-CH3), 3.68-4.30 (m,3H, 3b-H, 7b-H and12b-H), 4.75-6.00(m, 3H,-CH=CH2), (Ref. 0368)




(Ref. 0368/0476)



[0368] / [0476]
504
24-Nor-5b-chol-22-ene-3a,6a-diol
 BBA0504
Mizuho Une
C23H38O2 346.547 Download ChemDraw structure file

151-153 (as 3a-formate)(Ref. 0476)





(Ref. 0476)



[0476]
505
24-Nor-5b-chol-22-ene-3a,7a-diol
 BBA0505
Mizuho Une
C23H38O2 346.547 Download ChemDraw structure file

129.5-130(Ref. 0446)
3400,991,908 cm-1 (KBr disc) (Ref. 0446)
0.72(s,3H,18-CH3), 0.97(s,3H,19-CH3), 1.06(d, J=6Hz, 3H,21-CH3), 3.40-4.4 0 (m,2H, 3b-H, 7b-H), 4.90(m, 2H,23-H), 5.73(m,1H,22-H)(Ref. 0446)
m/z 400,385,345,310,295,255 (as TMS derivative)(Ref. 0446)



(Ref. 0446/0476)



[0446] / [0476]
506
24-Nor-5b-chol-22-ene-3a,7b-diol
 BBA0506
Mizuho Une
C23H38O2 346.547 Download ChemDraw structure file

122-124 (as aa-formate)(Ref. 0476)





(Ref. 0476)



[0476]
507
24-Nor-5b-chol-22-ene-3a,12a-diol
 BBA0507
Mizuho Une
C23H38O2 346.547 Download ChemDraw structure file

97-99 (as 3a-formate)(Ref. 0476)





(Ref. 0476)



[0476]
508
3a-Hydroxy-24-nor-5b-cholan-23-al
 BBA0508
Mizuho Une
C23H38O2 346.547 Download ChemDraw structure file

145(Ref. 0478)
[a]D=+13(Ref. 0478)
as 3a-acetate: 0.70(s,3H,18-CH3), 0.94(s,3H,19-CH3), 1.00(d, J=6Hz, 3H,21-CH3), 2.05(s,3H,OCOCH3), 2.0-2.5(m,2H,22-H), 4.73(m,1H,3b-H),9.76(m, 1H,-CHO) (CDCl3)(Ref. 0477)
as 3a-acetate: m/z 388,373,370,355,344,328,313,284,230,215 (Ref. 0477)



(Ref. 0477/0478)



[0477] / [0478]
509
3a,7a,12a-Trihydroxy-23,24-dinor-5b-cholan-22-al
 BBA0509
Mizuho Une
C22H36O4 364.519 Download ChemDraw structure file

KBr disc: 3400,1720,1075,1020,990,920,894 cm-1 (Ref. 0368)
0.78(s,3H,18-CH3), 1.00(s,3H,19-CH3), 1.28(d, J=6Hz, 3H,21-CH3), 3.68-4.09(m,3H, 3b-H, 7b-H, and 12b-H), 9.64(d,1H,-CHO)(Ref. 0368)




(Ref. 0368)



[0368]
510
3a,7a-Dihydroxy-23,24-dinor-5b-cholan-22-al
 BBA0510
Mizuho Une
C22H36O3 348.519 Download ChemDraw structure file

82.5-83.5 (Ref. 0446)
3400,1720 cm-1 (Ref. 0446)
0.68(s,3H,18-CH3), 0.96(s,3H,19-CH3), 1.08(d, J=6Hz, 3H,21-CH3), 3.4-4.4(m,2H, 3b-H, 7b-H), 9.73(d,J=3Hz,1H,-CHO) (pyridine-d5)(Ref. 0446)
as TMS derivative: m/z 492,402,312,292,255 (Ref. 0446)



(Ref. 0446)



[0446]
511
3a,7b-Dihydroxy-23,24-dinor-5b-cholan-22-al
 BBA0511
Mizuho Une
C22H36O3 348.519 Download ChemDraw structure file

3400,1720 cm-1 (Ref. 0448)
0.78(s,3H,18-CH3), 0.95(s,3H,19-CH3), 1.09(d, J=6Hz, 3H,21-CH3), 3.80(m,2H, 3b-H and 7a-H), 9.53(d,J=3Hz,1H,-CHO) (pyridine-d5)(Ref. 0448)




(Ref. 0448)



[0448]
512
3a,12a-Dihydroxy-23,24-dinor-5b-cholan-22-al
 BBA0512
Mizuho Une
C22H36O3 348.519 Download ChemDraw structure file

3400,1720 cm-1 (Ref. 0448)
0.73(s,3H,18-CH3), 0.94(s,3H,19-CH3), 1.23(d, J=6Hz, 3H,21-CH3), 3.80(m,1H, 3b-H), 4.07(m,1H,12b-H), 9.53(d,J=3Hz,1H,-CHO) (pyridine-d5)(Ref. 0448)




(Ref. 0448)



[0448]
513
5b-Cholane-3a,24-diol
 BBA0513
Mizuho Une
C24H42O2 362.589 Download ChemDraw structure file

177-178(Ref. 0471)
0.69(s,3H,18-CH3), 0.94(s,3H,19-CH3), 0.96(d, J=6Hz, 3H,21-CH3), 3.51(m,3H, 3b-H and 24-CH2OH)(CD3OD)(Ref. 0471)




(Ref. 0471/0473)



[0471] / [0473]
514
3a,7a,12a,24-Tetrahydroxy-24-ethyl-5b-cholestan-26-oic acid
 BBA0514
Mizuho Une
C29H50O6 494.704 Download ChemDraw structure file

198.5-199(Ref. 0479)





(Ref. 0479)



[0479]
515
3a,7a,12a-Trihydroxy-24-ethyl-5b-cholestan-26-oic acid
 BBA0515
Mizuho Une
C29H50O5 478.704 Download ChemDraw structure file

209-210(Ref. 0479)





(Ref. 0479)



[0479]
516
3a,7a,12a-Trihydroxy-24-carboxymethyl-5b-cholestan-26-oic acid
 BBA0516
Mizuho Une
C29H48O7 508.687 Download ChemDraw structure file


as methyl ester-acetate: m/z 571,560,542,482,313,253(Ref. 0411)



(Ref. 0411)



[0411]
517
3a,7a,12a-Trihydroxy-24-ethyl-5b-cholestan-26,27-dioic acid
 BBA0517
Mizuho Une
C29H48O7 508.687 Download ChemDraw structure file


as methyl ester-acetate: m/z 662,619,603,602,571,542,482,313,253 (Ref. 0411)



(Ref. 0411)



[0411]
518
3a,7a-Dihydroxy-24-ethyl-5b-cholestan-26-oic acid
 BBA0518
Mizuho Une
C29H50O4 462.705 Download ChemDraw structure file


as methyl ester-TMS: m/z 434,411,255(Ref. 0480)


Feces in sitosterol-fed monkey (Ref. 0480)




[0480]
519
3a-Hydroxy-24-ethyl-5b-cholestan-26-oic acid
 BBA0519
Mizuho Une
C29H50O3 446.705 Download ChemDraw structure file


as methyl ester-TMS: m/z 460,435,429,411,257 (Ref. 0480)


Feces in sitosterol-fed monkey (Ref. 0480)




[0480]
520
3b-Hydroxy-24-ethylcholest-5-en-26-oic acid
 BBA0520
Mizuho Une
C29H48O3 444.690 Download ChemDraw structure file


as methyl ester-TMS: m/z 381,357,255(Ref. 0480)


Feces in sitosterol-fed monkey (Ref. 0480)




[0480]
521
3a,7a,12a-Trihydroxy-24-methyl-5b-cholest-23-en-26-oic acid
 BBA0521
Mizuho Une
C28H46O5 462.662 Download ChemDraw structure file

182(Ref. 0391)





(Ref. 0391)



[0391]
522
3a,7a,12a-Trihydroxy-5b-cholestane-24-carboxylic acid
 BBA0522
Mizuho Une
C28H48O5 464.678 Download ChemDraw structure file

200(Ref. 0393)





(Ref. 0393)



[0393]
523
3a,7a,12a-Trihydroxy-5b-cholestane-26-carboxylic acid
 BBA0523
Mizuho Une
C28H48O5 464.678 Download ChemDraw structure file

25D:205-207, 25L:173-176(Ref. 0433)
25D:[a]D=+37, 25L:[a]D=+29(Ref. 0433)





(Ref. 0433)



[0433]
524
3a,7a,12a,26-Tetrahydroxy-5b-cholest-23-en-27-oic acid
 BBA0524
Mizuho Une
C27H44O6 464.635 Download ChemDraw structure file


as methyl ester-TMS: m/z 766,751,736,676,586,551,522,496,461,431,406,393,371,355,281,253,185,103 (Ref. 0481)


Toad bile(Ref. 0481)




[0481]
525
3a,7a,12a-Trihydroxy-5a-cholestane-26,27-dioic acid
 BBA0525
Mizuho Une
C27H44O7 480.634 Download ChemDraw structure file

CHCl3 (as methyl ester-acetate): 1710 cm-1(Ref. 0311)
as methyl ester-acetate(in pyridine-d5): 0.70(s,3H,18-CH3), 0.74(s,3H,19-CH3), 0.89(d, J=6Hz, 3H,21-CH3), 1.93,1.99,2.02(s,3H x 3,3-,7,12-OCOCH3), 3.68(s,6H,26- and 27-COOCH3), 5.14(m,2H,3b- and 7b-H),5.26(m,1H,12b-H)(Ref. 0333)




(Ref. 0311/0333)



[0311] / [0333]
526
3a,7a,12a-Trihydroxy-5b-cholestane-26,27-dioic acid
 BBA0526
Mizuho Une
C27H44O7 480.634 Download ChemDraw structure file

154-156(as diethyl ester)(Ref. 0330)
KBr disc (as diethyl ester) 1740,3440cm-1 (Ref. 0330)
as methyl ester-acetate(in pyridine-d5): 0.80(s,3H,18-CH3), 1.00(s,3H,19-CH3), 1.14(t,J=7Hz,6H,26-and 27-COOCH2CH3), 1.20(d, J=6Hz, 3H,21-CH3), 3.70(m,1H,3b-H), 4.07(m,1H, 7b-H), 4.18(q,J=7Hz,4H,26- and 27-COOCH2CH3), (Ref. 0330)




(Ref. 0310/0330)



[0310] / [0330]
527
3a,7a-Dihydroxy-5b-cholestane-26,27-dioic acid
 BBA0527
Mizuho Une
C27H44O6 464.635 Download ChemDraw structure file

CHCl3 (as diethyl ester): 1720,3400 cm-1 (Ref. 0365)
as methyl ester-acetate(in pyridine-d5): 0.69(s,3H,18-CH3), 0.95(d, J=6Hz, 3H,21-CH3), 0.97(s,3H,19-CH3), 1.17(t,J=6Hz,6H,26-and 27-COOCH2CH3), , 3.67(m,1H,3b-H), 3.95(m,1H, 7b-H), 4.17(q,J=6Hz,4H,26- and 27-COOCH2CH3), (Ref. 0365)




(Ref. 0365)



[0365]
528
3a,7b-Dihydroxy-5b-cholest-24-en-26-oic acid
 BBA0528
Mizuho Une
C27H44O4 432.636 Download ChemDraw structure file

KBr disc : 1640,1680,3400 cm-1 (Ref. 0400)
in pyridine-d5: 0.70(s,3H,18-CH3), 0.96(s,3H,19-CH3), 1.01(d, J=6Hz, 3H,21-CH3), 2.05(s,3H,27-CH3), , 3.70 (m,2H,3b-H and 7a-H), 7.02(t,J=6Hz,1H,24-H), (Ref. 0400)




(Ref. 0400)



[0400]
529
3a,12a-Dihydroxy-5b-cholest-24-en-26-oic acid
 BBA0529
Mizuho Une
C27H44O4 432.636 Download ChemDraw structure file

KBr disc : 1640,1680,3500 cm-1 (Ref. 0400)
in pyridine-d5: 0.73(s,3H,18-CH3), 0.93(s,3H,19-CH3), 1.18(d, J=6Hz, 3H,21-CH3), 2.03(s,3H,27-CH3), 3.75 (m,1H,3b-H), 4.11(m,1H,12b-H), 7.03(t,J=6Hz,1H,24-H), (Ref. 0400)
as methyl ester: m/z 446,428,413,410,395,319,301,299,289,283,281,273,271,255,253 (Ref. 0450)



(Ref. 0400/0450)



[0400] / [0450]
530
3a,7a-Dihydroxy-24-methyl-27-nor-5b-cholestan-26-oic acid
 BBA0530
Mizuho Une
C27H46O4 434.652 Download ChemDraw structure file

24R:179-181, 24S:197-199(Ref. 0482)
24R:[a]D=+18.5, 24S:[a]D=+8.7(Ref. 0482)
3610,3440,1725,1455,1430,1375,1160,1070,970,890 cm-1 (Ref. 0482)

as methyl ester: m/z 448,430,412,397,381,359,273,255,246,228,213 (Ref. 0482)



(Ref. 0482)



[0482]
531
3a-Hydroxy-5b-cholest-24-en-26-oic acid
 BBA0531
Mizuho Une
C27H44O3 416.636 Download ChemDraw structure file

188.5(Ref. 0402)
as methyl ester: lmax 219nm (24E), lmax 212nm(24Z) (Ref. 0450)
KBr disc: 1680,1640 cm-1 (Ref. 0402)

as methyl ester: m/z 412,397,303,285,283,273,257,255 (Ref. 0450)



(Ref. 0402/0450)



[0402] / [0450]
532
3a,7a,12a,24-Tetrahydroxy-27-nor-5b-cholestan-26-oic acid
 BBA0532
Mizuho Une
C26H44O6 452.624 Download ChemDraw structure file

as methyl ester: 183.5-184.5 (24S), 162.5-163.5 (24R) (Ref. 0342)
as methyl ester: [a]D=+35(24S), [a]D=+30(24R) (Ref. 0342)
as methyl ester (KBr disc): 3350,1710 cm-1 (Ref. 0342)
24S (in pyridine-d5): 0.76(s,3H,18-CH3), 0.95(s,3H,19-CH3), 1.17(d, J=6Hz, 3H,21-CH3), 3.45(s,3H,COOCH3), 3.58 (m,1H,3b-H), 3.94(m,1H,7b-H), 4.08(m,1H,12b-H), 4.20(m,1H,24-H) (Ref. 0342)




(Ref. 0342)



[0342]
533
3a,7a,12a-Trihydroxy-27-nor-5b-cholestan-26-oic acid
 BBA0533
Mizuho Une
C26H44O5 436.625 Download ChemDraw structure file

195(Ref. 0433)
[a]D=+34(methanol) (Ref. 0433)





(Ref. 0433/0483/0484)



[0433] / [0483] / [0484]
534
3a,7a,12a,23-Tetrahydroxy-26,27-dinor-5b-cholestan-25-oic acid
 BBA0534
Mizuho Une
C25H42O6 438.597 Download ChemDraw structure file

188-189 (23R), 238.5-240(23S)(Ref. 0485)
as methyl ester (KBr disc) 23S: 3400,1740 cm-1;23R: 3400,1749 cm-1 (Ref. 0485)
23R: 0.84(s,3H,18-CH3), 0.98(s,3H,19-CH3), 1.33(d, J=6Hz, 3H,21-CH3), 3.64 (m,1H,3b-H), 4.01(m,1H,7b-H), 4.21(m,1H,12b-H), 4.61(m,1H,23-H) (Ref. 0485)




(Ref. 0379/0485)



[0379] / [0485]
535
3a,6b,7a-Trihydroxy-26,27-dinor-5b-cholestan-25-oic acid
 BBA0535
Mizuho Une
C25H42O5 422.598 Download ChemDraw structure file

240-241.5(Ref. 0307)
KBr disc : 3400,1700 cm-1 (Ref. 0307)
0.76(s,3H,18-CH3), 0.99(d, J=6Hz, 3H,21-CH3), 1.44(s,3H,19-CH3), 3.80 (m,1H,3b-H), 4.21(m,2H,6a- and 7b-H)(Ref. 0307)




(Ref. 0307)



[0307]
536
3a,7a,12a-Trihydroxy-26,27-dinor-5a-cholestan-25-oic acid
 BBA0536
Mizuho Une
C25H42O5 422.598 Download ChemDraw structure file

198-200(Ref. 0313)





(Ref. 0313)



[0313]
537
3a,7a,12a-Trihydroxy-26,27-dinor-5b-cholestan-25-oic acid
 BBA0537
Mizuho Une
C25H42O5 422.598 Download ChemDraw structure file

215-216(Ref. 0433), 215-215.5(Ref. 0486)





(Ref. 0376/0433/0486)



[0376] / [0433] / [0486]
538
3a,7b,12a-Trihydroxy-26,27-dinor-5b-cholestan-25-oic acid
 BBA0538
Mizuho Une
C25H42O5 422.598 Download ChemDraw structure file

185.5-186(Ref. 0487)
0.85(s,3H,18-CH3), 1.01(s,3H,19-CH3), 1.20(d, J=6Hz, 3H,21-CH3), 3.70-4.00(m,2H,3b-H and 7a-H), 4.23(m,1H,12b-H)(Ref. 0487)




(Ref. 0487)



[0487]
539
3a,12a-Dihydroxy-7-oxo-26,27-dinor-5b-cholestan-25-oic acid
 BBA0539
Mizuho Une
C25H40O5 420.582 Download ChemDraw structure file

213-214(Ref. 0487)
0.75(s,3H,18-CH3), 1.15(d, J=6Hz, 3H,21-CH3), 1.20(s,3H,19-CH3), 3.80(m,1H,3b-H), 4.20(m,1H, 12b-H)(Ref. 0487)




(Ref. 0487)



[0487]
540
3a,7b-Dihydroxy-26,27-dinor-5b-cholestan-25-oic acid
 BBA0540
Mizuho Une
C25H42O4 406.599 Download ChemDraw structure file

174-175(Ref. 0487)

as methyl ester-TMS derivative: m/z 564,549,474,459,384,369,345,255(Ref. 0487)



(Ref. 0487)



[0487]
541
3a,7b-Dihydroxy-26,27-dinor-5b-cholest-11-en-25-oic acid
 BBA0541
Mizuho Une
C25H40O4 404.583 Download ChemDraw structure file

as methyl ester-acetate:0.72(s,3H,18-CH3), 0.85(s,3H,19-CH3), 0.96(d, J=6Hz, 3H,21-CH3), 2.02(s,6H,3a- and 7b-OCOCH3), 3.62(s,3H, COOCH3), 4.6-5.0(m,2H,3b-H and 7a-H)(Ref. 0487)




(Ref. 0487)



[0487]
542
3a-Hydroxy-7-oxo-26,27-dinor-5b-cholestan-25-oic acid
 BBA0542
Mizuho Une
C25H40O4 404.583 Download ChemDraw structure file

185-186(Ref. 0488)
pyridine-d5: 0.62(s,3H,18-CH3), 0.97(s,3H,19-CH3), 1.14(d, J=6Hz, 3H,21-CH3), 3.81(m,1H,3b-H) (Ref. 0487)




(Ref. 0487)



[0487] / [0488]
543
3a-Hydroxy-26,27-dinor-5b-cholestan-25-oic acid
 BBA0543
Mizuho Une
C25H42O3 390.599 Download ChemDraw structure file

129-130(Ref. 0488)
pyridine-d5: 0.65(s,3H,18-CH3), 0.96(s,3H,19-CH3), 0.97(d, J=6Hz, 3H,21-CH3), 3.98(m,1H,3b-H) (Ref. 0488)




(Ref. 0488)



[0488]
544
3a-Hydroxy-26,27-dinor-5b-cholest-6-en-25-oic acid
 BBA0544
Mizuho Une
C25H40O3 388.583 Download ChemDraw structure file

138.5-139.5(Ref. 0307)
KBr disc: 3300,1700 cm-1(Ref. 0307)
pyridine-d5: 0.64(s,3H,18-CH3), 0.92(s,3H,19-CH3), 0.98(d, J=6.6Hz, 3H,21-CH3), 5.50(d,J=10.6Hz,1H, 6-H), 5.65(ddd,J1=10.1Hz,J2=4.6Hz,J3=2.6Hz,1H,7-H)(Ref. 0307)




(Ref. 0307)



[0307]
545
7a-Hydroxy-3-oxo-26,27-dinor-5a-cholestan-25-oic acid
 BBA0545
Mizuho Une
C25H40O4 404.583 Download ChemDraw structure file

189-191(as methyl ester)(Ref. 0451)
as nujol mulis (methyl ester): 3533,1745,1709,1278,1231,1197,1162,1077,1039,1020,1005,963,952,892 cm-1(Ref. 0451)

as methyl ester-TMS: m/z 490,475,400,385,369,367,334,330,319,271,244 (Ref. 0451)



(Ref. 0451)



[0451]
546
7a-Hydroxy-3-oxo-26,27-dinorcholest-4-en-25-oic acid
 BBA0546
Mizuho Une
C25H38O4 402.567 Download ChemDraw structure file

211-212(Ref. 0456)
lmax 243nm(Ref. 0456)
3508,3154,1724,1666,1310,1282,1265,1237,1186,1117,1066,1041,1006,945 cm-1 (Ref. 0456)
0.71(s,3H,18-CH3), 0.93(d, J=6Hz, 3H,21-CH3), 1.18(s,3H,19-CH3), 3.95(m,1H,7b-H), 5.78(m,1H,4-H) (Ref. 0456)
m/z 402,384,374,369,366,346,269,261,249,227,124(Ref. 0456)



(Ref. 0456)



[0456]
547
7a-Hydroxy-3-oxo-26,27-dinor-5b-cholestan-25-oic acid
 BBA0547
Mizuho Une
C25H40O4 404.583 Download ChemDraw structure file

131-132(Ref. 0456)
3597,1745,1718,1191,1162,1119,1071,985,975 cm-1 (Ref. 0456)

as methyl ester-TMS: m/z 490,475,400,385,369,367,271,229 (Ref. 0456)



(Ref. 0451/0456)



[0451] / [0456]
548
3a,7a-Dihydroxy-26,27-dinor-5b-cholestan-25-oic acid
 BBA0548
Mizuho Une
C25H42O4 406.599 Download ChemDraw structure file

210-212(Ref. 0364)
2935,2865,1692,1365,1265,1068,965 cm-1 (Ref. 0364)

as methyl ester: m/z 406,388,370,355,301,255,228,201 (Ref. 0364)



(Ref. 0364)



[0364]
549
3b,7a,12a-Trihydroxy-26,27-dinor-5b-cholestan-25-oic acid
 BBA0549
Mizuho Une
C25H42O5 422.598 Download ChemDraw structure file

196-198(Ref. 0489)
[a]D=+33(Ref. 0489)
DMSO: 0.59(s,3H,18-CH3), 0.83(s,3H,19-CH3), 0.93(d, J=6Hz, 3H,21-CH3), 3.61(q,J=3.0Hz,7b-H), 3.78(m,2H,3a-H and 12b-H)(Ref. 0489)




(Ref. 0489)



[0489]
550
7a,12a-Dihydroxy-3-oxo-26,27-dinor-5b-cholestan-25-oic acid
 BBA0550
Mizuho Une
C25H40O5 420.582 Download ChemDraw structure file






(Ref. 0489)



[0489]
551
2b,3b-Dihydroxy-6-oxo-5a-chol-7-en-24-oic Acid
 BBA0601
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

225degC(Ref. 0082)









[0082]
552
(20S,22E)-3b-Hydroxychola-5,16,22-trien-24-oic Acid
 BBA0602
Takashi Iida
C24H34O3 370.525 Download ChemDraw structure file

121-122degC (Me ester-3-acetate)(Ref. 0235)
[a]D: -66.9deg (CHCl3) (Me ester-3-acetate)(Ref. 0235)
Me ester-3-acetate: nmaxmcm-1: 1720, 1650, 1030, 980(Ref. 0235)
Me ester-3-acetate 1H-NMR (CDCl3) d: 0.81(s), 1.08(s), 1.22(d, J, 7.0), 3.04(qt, J, 7.8), 3.75(s), 5.43(m), 5.80(dd, J, 16.0, 1.5), 6.92(dd, J, 16.0, 8.0)(Ref. 0235)
Me ester-3-acetate 13C-NMR (CDCl3) d: 16.1, 19.1, 19.8, 20.6, 21.3, 27.6, 30.3, 31.1, 31.3, 34.8, 35.0, 36.6, 36.8, 38.0, 47.0, 50.3, 51.3, 56.8, 73.7, 119.0, 122.3, 123.8, 139.7, 153.4, 156.2, 167.2, 170.3(Ref. 0235)
Me ester-3-acetate (70eV) m/z: 366(M-AcOH, 100%), 351(2.89%), 253(2.78%)(Ref. 0235)







[0235]
553
3a-Hydroxy-5b,14b-chol-8-en-24-oic Acid
 BBA0603
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

186-187degC(Ref. 0240)
[a]D: +96.3deg (MeOH)(Ref. 0240)
lmax (EtOH) (e): 200(8020), 202(8000), 205(5940), 210(4750), 215(1980), 220(850) nm(Ref. 0240)
nmaxmcm-1: 1730(C=O), 3330(OH)(Ref. 0240)
Me ester 1H-NMR (CDCl3; 60MHz) d: 0.95, -CH3 1.01, -OH 1.85, -COOMe 3.68(Ref. 0240)
(70eV) m/z: 374(M+), 359, 356, 341, 302(100%), 255, 229, 215(Ref. 0240)
Me ester (70eV) m/z: 388(M+), 370, 355, 316(100%), 255, 229, 213, 201(Ref. 0240)







[0240]
554
(20S,22E)-3b-Hydroxychola-5,22-dien-24-oic Acid
 BBA0604
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

151-151.5degC (Me ester-3-acetate)(Ref. 0096)
[a]D: -85deg (C=0.14, CHCl3) (Me ester-3-acetate)(Ref. 0096)
Me ester-3-acetate: lmax (e): 218(13000) nm(Ref. 0096)
Me ester-3-acetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.65(s), 19-Me 1.00(s), 21-Me 1.00(d), 3b-OCOMe 2.04(s), COOMe 3.74(s), 3a-H 4.60(m), 6-H 5.38(m), 23-H 5.87(d, J, 16.0), 22-H 6.87(dd, J, 16.0, 9.5)(Ref. 0096)
Me ester-3-acetate (70eV) m/z: 397(1%), 369(29%), 368(100%), 353(9%), 255(9%), 215(2%), 213(7%), 199(3%), 197(2%), 187(6%), 185(2%), 173(4%), 171(3%), 161(9%), 159(12%), 157(5%), 147(19%), 145(17%), 143(8%), 133(15%), 131(9%), 121(15%), 119(12%), 114(8%), 107(20%), 105(19%), 93(17%), 91(15%), 81(24%), 79(14%), 67(12%), 55(12%), 43(22%), 41(9%)(Ref. 0096)







[0096]
555
(22E)-3b-Hydroxychola-5,22-dien-24-oic Acid
 BBA0605
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

151.5-152degC (Me ester-3-acetate)(Ref. 0096)
[a]D: -54.3deg (C=0.09, CHCl3) (Me ester-3-acetate)(Ref. 0096)
Me ester-3-acetate: lmax (e): 210(16100) nm(Ref. 0096)
Me ester-3-acetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.74(s), 19-Me 1.01(s), 21-Me 1.08(d), 3b-OCOMe 2.03(s), COOMe 3.74(s), 3a-H 4.63(m), 6-H 5.36(m), 23-H 5.76(d, J, 16.0), 22-H 6.87(dd, J, 16.0, 9.5)(Ref. 0096)
Me ester-3-acetate (70eV) m/z: 397(1%), 369(29%), 368(100%), 353(7%), 255(10%), 215(2%), 213(7%), 199(3%), 197(2%), 187(5%), 185(2%), 173(4%), 171(3%), 161(8%), 159(11%), 157(5%), 147(18%), 146(16%), 143(6%), 133(14%), 131(8%), 121(14%), 119(10%), 114(8%), 107(19%), 105(17%), 93(15%), 91(13%), 81(23%), 79(12%), 67(11%), 55(12%), 43(19%), 41(8%)(Ref. 0096)







[0096]
556
(20S)-3b-Hydroxychol-5-en-24-oic Acid
 BBA0606
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

119-120degC (Me ester-3-acetate)(Ref. 0096)
[a]D: -54pm3deg (C=0.9, CHCl3) (Me ester-3-acetate)(Ref. 0096)
Me ester-3-acetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.70(s), 21-Me 0.84(d), 19-Me 1.03(s), 3b-OCOMe 2.04(s), COOMe 3.68(s), 3a-H 4.60(m), 6-H 5.39(m)(Ref. 0096)
Me ester-3-acetate (70eV) m/z: 371(29%), 370(100%), 355(16%), 339(5%), 262(10%), 255(15%), 249(27%), 213(14%), 161(12%), 160(11%), 159(14%), 145(35%), 143(26%), 141(11%), 135(10%), 133(15%), 131(11%), 121(18%), 120(16%), 119(15%), 109(11%), 107(26%), 105(23%), 95(18%), 93(21%), 91(17%), 81(29%), 79(14%), 67(17%), 55(24%), 43(23%), 41(11%)(Ref. 0096)


Isolated from the marine invertebrate Ptilosarcus gurneyi (sea pen).(Ref. 0096)




[0096]
557
(20S)-3b-Hydroxy-5a-cholan-24-oic Acid
 BBA0607
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

136-137.5degC (Me ester-3-acetate)(Ref. 0096/0235)
[a]D: +6.4deg (C=0.125, CHCl3) (Me ester-3-acetate)(Ref. 0096)
Me ester-3-acetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.68(s), 21-Me 0.83(d), 19-Me 0.83(s), 3b-OCOMe 2.03(s), COOMe 3.68(s), 3a-H 4.68(m)(Ref. 0096/0235)
Me ester-3-acetate (70eV) m/z: 432(M+, 11%), 417(1%), 372(97%), 357(24%), 290(20%), 276(13%), 275(19%), 264(9%), 257(5%), 249(3%), 230(35%), 217(26%), 216(40%), 215(100%), 201(16%), 161(13%), 159(10%), 154(10%), 149(18%), 147(49%), 145(20%), 135(18%), 133(17%), 123(19%), 121(29%), 119(23%), 109(25%), 107(43%), 105(25%), 95(43%), 93(39%), 91(20%), 81(51%), 79(27%), 69(18%), 67(32%), 55(42%), 43(44%), 41(21%)(Ref. 0096)







[0096] / [0235]
558
(20S,22E)-3b-Hydroxy-5a-chol-22-en-24-oic Acid
 BBA0608
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

122-123degC (Me ester-3-acetate)(Ref. 0096)
[a]D: +18pm3deg (C=0.57, CHCl3) (Me ester-3-acetate)(Ref. 0096)
Me ester-3-acetate: lmax (e): 219(6500) nm(Ref. 0096)
Me ester-3-acetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.62(s), 19-Me 0.80(s), 21-Me 0.98(d), OCOMe 2.02(s), COOMe 3.73(s), 3a-H 4.66(m), 23-H 5.76(d, J, 16.0), 22-H 6.89(dd, J, 16.0, 9.5)(Ref. 0096)
Me ester-3-acetate (70eV) m/z: 430(M+, 6%), 415(2%), 370(34%), 257(72%), 215(33%), 201(10%), 175(8%), 163(9%), 161(22%), 149(20%), 147(34%), 135(17%), 133(16%), 123(11%), 121(24%), 119(16%), 114(100%), 109(20%), 107(53%), 105(20%), 95(34%), 93(38%), 91(18%), 81(53%), 79(26%), 69(10%), 67(27%), 55(25%), 43(33%), 41(16%)(Ref. 0096)







[0096]
559
3,12-Dioxochola-1,4,9(11)-trien-24-oic Acid
 BBA0609
Takashi Iida
C24H30O4 382.493 Download ChemDraw structure file

137-139degC (Me ester)(Ref. 0119)
[a]d-20: +72deg (C=1.0, CHCl3) (Me ester)(Ref. 0119)
Me ester: lmax (EtOH) (e): 237(28300) nm(Ref. 0119)
Me ester: nmaxmcm-1: 1745, 1680, 1665, 1625, 1615, 1600(Ref. 0119)
Me ester 1H-NMR(CDCl3; 60MHz) d: 18- and 21-Me 0.95(br), 19-Me 1.50(s), COOMe 3.59(s), 4-H 5.66(d, J, 2.0), 11-H 6.05(br), 2-H 6.23(dd, J, 10.0, 2.0), 1-H 7.01(d, J, 10.0)(Ref. 0119)








[0119]
560
5b-Chola-8(14),11-dien-24-oic Acid
 BBA0610
Takashi Iida
C24H36O2 356.541 Download ChemDraw structure file

136-137degC, (Me ester ; mp, 73-74degC)(Ref. 0099)
[a]d-20: +36pm2deg (CHCl3)(Ref. 0099)
[a]d-21: +35.2deg (CHCl3) (Me ester)(Ref. 0099)
lmax (EtOH)(e): 213(5100) nm(Ref. 0099)









[0099]
561
5b-Chola-3,8(14),11-trien-24-oic Acid
 BBA0611
Takashi Iida
C24H34O2 354.526 Download ChemDraw structure file

132-134degC(Ref. 0099)
[a]d-21: +25pm2deg (CHCl3)(Ref. 0099)
lmax (EtOH)(e): 213(6300) nm(Ref. 0099)









[0099]
562
5b-Chola-7,9(11)-dien-24-oic Acid
 BBA0612
Takashi Iida
C24H36O2 356.541 Download ChemDraw structure file

156-158degC, (Me ester ; mp, 105-107degC)(Ref. 0099)
[a]d-19: +107pm2deg (CHCl3)(Ref. 0099)
[a]d-19: +106pm1deg (CHCl3) (Me ester)(Ref. 0099)
Me ester: lmax (EtOH) (e): 244(13800) nm(Ref. 0099)









[0099]
563
3a-Hydroxy-5b-chola-8(14),11-dien-24-oic Acid
 BBA0613
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

165-167degC, (Me ester ; mp, 124-125degC)(Ref. 0099)
[a]d-20: +35pm2deg (CHCl3)(Ref. 0099)
[a]d-25: +40pm2deg (CHCl3) (Me ester)(Ref. 0099)
lmax (EtOH) (e): 212(4900) nm(Ref. 0099)









[0099]
564
3a-Hydroxy-5b-chola-7,9(11)-dien-24-oic Acid
 BBA0614
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

200-201degC, (Me ester ; mp, 119-120degC)(Ref. 0099)
[a]d-25: +121pm2deg (dioxane)(Ref. 0099)
[a]d-25: +122pm2deg (dioxane) (Me ester)(Ref. 0099)
lmax (EtOH) (e): 244(10700) nm(Ref. 0099)









[0099]
565
3-Oxo-5b-chola-8(14),11-dien-24-oic Acid
 BBA0615
Takashi Iida
C24H34O2 354.526 Download ChemDraw structure file

120-122degC (Me ester)(Ref. 0099)
[a]d-25: +43pm2deg (CHCl3) (Me ester)(Ref. 0099)
Me ester: lmax (EtOH) (e): 214(3700) nm(Ref. 0099)









[0099]
566
3-Oxo-5b-chola-7,9(11)-dien-24-oic Acid
 BBA0616
Takashi Iida
C24H34O2 354.526 Download ChemDraw structure file

144degC (Me ester)(Ref. 0099/0104)
[a]d-21: +88deg (CHCl3) (Me ester)(Ref. 0099/0104)
Me ester: lmax (EtOH)(e): 245(10920) nm(Ref. 0099/0104)
Me ester: nmaxmcm-1: 1738,1709(C=O), 800(=C-H)(Ref. 0104)









[0099] / [0104]
567
3-Oxo-5b-chola-7,11-dien-24-oic Acid
 BBA0617
Takashi Iida
C24H34O2 354.526 Download ChemDraw structure file

148-149degC (Me ester)(Ref. 0099)
[a]16D: +74pm3deg (Ref. 0099)









[0099]
568
3a-Hydroxy-5a-chol-6-en-24-oic Acid
 BBA0618
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

164-165degC (Me ester-3-acetate)(Ref. 0036)
[a]d-25: -28deg (C=0.88, benzene) (Me ester-3-acetate)(Ref. 0036)
Me ester-3-acetate: nmaxmcm-1: 1739, 1261, 1235, 1170, 1020(3a-OCOMe-5a-), 843(Ref. 0036)

Me ester-3-acetate (70eV) m/z: 249(100%)(Ref. 0036)







[0036]
569
3b-Hydroxy-19-oxochol-5-en-24-oic Acid
 BBA0619
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

164-166degC (Me ester-3-acetate)(Ref. 0236)
Me ester-3-acetate: nmaxcm-1: 1260, 1720, 2700(Ref. 0236)
Me ester-3-acetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.62(s), 3b-OCOMe 2.01(s), COOMe 3.64(s), 3a-H 4.57(br), vinylic-H 5.88(m), 19-CHO 9.64(s)(Ref. 0236)








[0236]
570
3a,11-Dihydroxy-12-oxo-5b-chol-9(11)-en-24-oic Acid
 BBA0620
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

168-169degC(Ref. 0077)









[0077]
571
3a,11a-Dihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0621
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

191-193degC(Ref. 0087)
151-152degC (Me ester-3-formate)(Ref. 0077)
150-151degC (Me ester-3,11-diacetate)(Ref. 0261)
[a]d-25: +69.0pm2deg (C=1.252, EtOH)(Ref. 0087)
[a]d-25: +91.2deg (C=1.0, CHCl3) (Me ester-3-formate)(Ref. 0077)
[a]d-24: +34.9deg (C=0.99, EtOH) (Me ester-3,11-diacetate)(Ref. 0261)
lmax (EtOH)(loge): 278(1.90) nm(Ref. 0087)









[0077] / [0087] / [0261]
572
3a,11b-Dihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0622
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

180.5-182degC (Me ester-3-formate)(Ref. 0077)
159-161degC (Me ester-3-acetate)(Ref. 0261)
[a]d-25: +119.6deg (C=1.0, CHCl3) (Me ester-3-formate)(Ref. 0077)
[a]d-22: +118.4deg (C=0.88, EtOH) (Me ester-3-acetate)(Ref. 0261)









[0077] / [0261]
573
3b,5a,6b-Trihydroxycholan-24-oic Acid
 BBA0623
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

242-243degC, (Me ester ; mp, 203-205degC)(Ref. 0112/0237)
[a]d-21: -10.3pm2deg (C=0.987, pyridine)(Ref. 0112/0237)
[a]d-20: -7.6pm2deg (C=0.996, pyridine) (Me ester)(Ref. 0112/0237)
Me ester: nmaxmcm-1: 1710, 1692, 1674(C=O), 3575, 3433, 3000(OH)(Ref. 0112)









[0112] / [0237]
574
(22E)-3b-Hydroxy-5a-chola-16,22-dien-24-oic Acid
 BBA0624
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

105-106degC (Me ester-3-acetate)(Ref. 0224)
[a]d-25: +30.0deg (C=1.0, CHCl3) (Me ester-3-acetate)(Ref. 0224)
Me ester-3-acetate 1H-NMR(CDCl3) d: 18-Me 0.74(s), 19-Me 0.83(s), 21-Me 1.16(d), 20-H 2.98(qd, J, 7.0, 8.0), COOMe 3.69(s), 16-H 5.39(m), 23-H 5.78(dd, J, 1.5, 16.0), 22-H 6.92(dd, J, 8.0, 16.0)(Ref. 0224)








[0224]
575
(22E)-3b-Hydroxychola-5,16,22-trien-24-oic Acid
 BBA0625
Takashi Iida
C24H34O3 370.525 Download ChemDraw structure file

124-125degC (Me ester-3-acetate)(Ref. 0224/0234)
[a]d-25: -24.8deg (C=1.0, CHCl3) (Me ester-3-acetate)(Ref. 0224/0234)
Me ester: nmaxmcm-1: 980, 1020, 1650, 1720(Ref. 0234)
Me ester-3-acetate 1H-NMR(CDCl3) d: 18-Me 0.78(s), 19-Me 1.03(s), 21-Me 1.17(d), 20-H 3.00(qd, J, 7.0, 8.0), COOMe 3.69(s), 16- and 6-H 5.40(m), 23-H 5.80(dd, J, 1.5, 16.0), 22-H 6.92(dd, J, 8.0, 16.0)(Ref. 0224/0234)
13C-NMR (CDCl3) d: C-18 16.42(Ref. 0234)
Me ester-3-acetate 13C-NMR (CDCl3) d: C-18 16.17(Ref. 0234)








[0224] / [0234]
576
(22E)-1a,3b-Dihydroxychola-5,16,22-trien-24-oic Acid
 BBA0626
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

amorphous solid (Me ester-3-acetate)(Ref. 0224)
[a]d-25: +5.5deg (C=1.0, CHCl3) (Me ester-3-acetate)(Ref. 0224)
Me ester-3-acetate 1H-NMR(CDCl3) d: 18-Me 0.75(s), 19-Me 1.08(s), 21-Me 1.14(d), 20-H 2.98(qd, J, 7.0, 8.0), 16-H 5.38(brs), 6-H 5.51(m), 23-H 5.77(dd, J, 1.0, 16.0), 22-H 6.90(dd, J, 8.0, 16.0)(Ref. 0224)








[0224]
577
15a-Hydroxy-5b-cholan-24-oic Acid
 BBA0627
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

193-195degC(Ref. 0070)
1H-NMR (Pyridine-d5) d: 18-Me 0.71(s), 19-Me 0.95(s)(Ref. 0070)
Me ester 1H-NMR (Pyridine-d5) d: 18-Me 0.67(s), 19-Me 0.93(s), COOMe 3.55(s)(Ref. 0070)
Me ester m/z: 376(M+), 358(M-H2O), 257(100%),(Ref. 0070)







[0070]
578
15-Oxo-5b-cholan-24-oic Acid
 BBA0628
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file


Me ester m/z: 388(M+), 273(100%), 246, 218(Ref. 0070)







[0070]
579
3,7,23-Trioxo-5b-cholan-24-oic Acid
 BBA0629
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

156-158degC (Me ester)(Ref. 0054)
[a]D: -36deg (C=0.6, CHCl3) (Me ester)(Ref. 0054)
Me ester: nmaxcm-1: 1721, 1709, 1435(Ref. 0054)
Me ester 1H-NMR(CDCl3; 80MHz) d: 18-Me 0.74(s), 19-Me 1.31(s), 21-Me 0.93(d), 22-H2 2.62(dd, J, 17.0, 3.1) and 2.89(dd, J, 17.0, 3.1), COOMe 3.86(s)(Ref. 0054)








[0054]
580
(23R)-23-Hydroxy-3,7-dioxo-5b-cholan-24-oic Acid
 BBA0630
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

160-161degC (Me ester)(Ref. 0054)
[a]D: -40deg (C=0.5, CHCl3) (Me ester)(Ref. 0054)
Me ester: nmaxcm-1: 3530, 1728, 1709, 1435(Ref. 0054)
Me ester 1H-NMR(CDCl3; 80MHz) d: 18-Me 0.73(s), 19-Me 1.30(s), 21-Me 1.02(d), COOMe 3.78(s), 23-H2 4.23(dd, J, 10.5, 2.0)(Ref. 0054)








[0054]
581
3a,12a-Dihydroxy-5b-chol-14-en-24-oic Acid
 BBA0631
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

259-260degC, (Me ester; mp, 88.5-90degC)(Ref. 0058/0253)
[a]d-21: +67.8deg (C=0.258, EtOH), [a]16D: +60.4deg (C=0.867, CHCl3) (Me ester), [a]15.5D: +102.5deg (C=1.168, CHCl3) (Me ester-3,12-diacetate)(Ref. 0253)
Me ester 1H-NMR(CDCl3; 60MHz) d: 18- and 19-Me 0.92(s), 15-H 5.29(Ref. 0058)
Me eater m/z: 404(M+), 386, 368, 271, 253(Ref. 0058)







[0058] / [0253]
582
3a,12a-Dihydroxy-5b-chola-7,14-dien-24-oic Acid
 BBA0632
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

247-248degC(Ref. 0253)
98-98.5degC (Me ester-3,12-diacetate)(Ref. 0253)
[a]D: -60.0deg (C=0.382, EtOH), [a]20.5D: +6.3deg (C=1.032, CHCl3) (Me ester-3,12-diacetate)(Ref. 0253)
Me ester-3,12-diacetate: lmax (EtOH) (loge): 242(4.08) mm(Ref. 0253)









[0253]
583
3a,12a-Dihydroxy-5b-chola-8,14-dien-24-oic Acid
 BBA0633
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

250.5-251degC(Ref. 0253)
121-121.5degC (Me ester-3,12-diacetate)(Ref. 0253)
[a]d-17: +71.6deg (C=0.318, EtOH), [a]14.5D: +165.2deg (C=0.230, CHCl3) (Me ester-3,12-diacetate)(Ref. 0253)
Me ester-3,12-diacetate: lmax (EtOH) (loge): 244(4.25) mm(Ref. 0253)









[0253]
584
3a-Hydroxy-7-oxo-5b-chol-11-en-24-oic Acid
 BBA0634
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

219-221degC(Ref. 0075)
Me ester 1H-NMR(CDCl3; 79.54MHz) d: olefinic protons 5.31 and 6.15(Ref. 0075)








[0075]
585
3,12-Dioxo-5b-chol-6-en-24-oic Acid
 BBA0635
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

178.5-180degC, (Me ester; mp, 157-159degC)(Ref. 0132)
[a]d-21: 0pm2deg (C=1.4) (Me ester)(Ref. 0132)









[0132]
586
6b,7a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0636
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

106-107degC (Me ester)(Ref. 0132/0246)
[a]d-21: +8pm1deg (C=2.0, CHCl3) (Me ester)(Ref. 0132/0246)









[0132] / [0246]
587
6b,7b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0637
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

114-115degC (Me ester)(Ref. 0132/0246)
[a]d-19: +52pm3deg (C=1.5, CHCl3) (Me ester)(Ref. 0132/0246)









[0132] / [0246]
588
3a,7a-Dihydroxy-11-oxo-5b-cholan-24-oic Acid
 BBA0638
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

204degC (Me ester-3,7-diacetate)(Ref. 0242)
[a]D: +30.8deg (CHCl3) (Me ester-3,7-diacetate)(Ref. 0242)
Me ester-3,7-diacetate: lmax (EtOH) (e): 290(68) nm(Ref. 0242)
Me ester: nmaxcm-1: 1732, 1703, 1255(Ref. 0242)
Me ester-3,7-diacetate 1H-NMR(CDCl3) d: 18-Me 0.62(s), 19-Me 1.15(s), 3a-OCOMe 2.03(s), 7a-OCOMe 2.12(s), COOMe 3.65(s), 3b-H 4.53(m), 7b-H 5.00(m)(Ref. 0004/0242)
Me ester-3,7-diacetate m/z: 504(M+, 7%), 444(M-AcOH, 25%), 429(15%), 384(M-2AcOH, 100%), 351(37%), 291(79%)(Ref. 0242)







[0004] / [0242]
589
Chola-3,5-dien-24-oic Acid
 BBA0639
Takashi Iida
C24H36O2 356.541 Download ChemDraw structure file

96-98degC (Me ester)(Ref. 0089/0090)
[a]D: -128deg (C=1.09, CHCl3) (Me ester)(Ref. 0089/0090)
Me ester: lmax (MeOH) (loge): 227.5(4.28), 235(4.32), 243(4.12) nm(Ref. 0089/0090)









[0089] / [0090]
590
5b-Chol-2-en-24-oic Acid
 BBA0640
Takashi Iida
C24H38O2 358.557 Download ChemDraw structure file

Me ester 1H-NMR(CDCl3) d: 18-Me 0.65(s), 21-Me 0.90(d), 19-Me 0.96(s), COOMe 3.66(s), 3-H 5.48-5.56(m), 2-H 5.59-5.64(m)(Ref. 0225)








[0225]
591
3a,12a-Dihydroxy-15-oxo-5b-chol-8(14)-en-24-oic Acid
 BBA0641
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

188-192degC(Ref. 0107)
[a]D: +97.7deg (C=0.825, EtOH)(Ref. 0107)
[a]D: +130.3deg (C=1.085, dioxane) (Me ester)(Ref. 0107)
Me ester 1H-NMR(CDCl3) d: 18-Me 0.99(s), 19-Me 0.84(s), 21-Me 1.025(d), COOMe 3.67(s), 7-H 4.10(m)(Ref. 0107)








[0107]
592
3a,12a,15b-Trihydroxy-5b-chol-8(14)-en-24-oic Acid
 BBA0642
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

185-189degC (Me ester-3,12-diacetate)(Ref. 0107)
[a]D: +67.3deg (C=1.285, dioxane) (Me ester-3,12-diacetate)(Ref. 0107)
Me ester-3,12-diacetate: nmaxcm-1: 3610, 2880, 1735, 1378, 1365, 1235, 1030(Ref. 0107)
Me ester-3,12-diacetate 1H-NMR(CDCl3) d: 18-Me 1.07(s), 19-Me 0.83(s), 21-Me 0.86(d), 3a- and12a-OCOMe 2.01(s) and 2.02(s), COOMe 3.65(s), 3b-H 4.60(m), 12b-H 5.025(t), 15a-H 4.75(m)(Ref. 0107)
Me ester-3,12-diacetate 13C-NMR(CDCl3) d: C-1 34.1, C-2 27.7, C-3 73.9, C-4 32.1, C-5 41.8, C-6 27.0, C-7 23.5, C-8 134.0, C-9 32.9, C-10 36.5, C-11 23.8, C-12 74.5, C-13 44.6, C-14 141.0, C-15 69.4, C-16 37.5, C-17 45.1, C-18 20.0, C-19 23.8, C-20 32.0, C-21 17.9, C-22 30.9, C-23 30.6, C-24 174.4, C-25 51.5(Ref. 0107)








[0107]
593
3a-Hydroxy-12-oxo-5b-chol-7-en-24-oic Acid
 BBA0643
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

139-140degC (Me ester-3-acetate)(Ref. 0116)
[a]14D: +143.8pm2deg (C=1.690, CHCl3) (Me ester-3-acetate)(Ref. 0116)









[0116]
594
3,12-Dioxo-5b-chol-7-en-24-oic Acid
 BBA0644
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

172-176degC, (Me ester; mp, 140-141degC)(Ref. 0116)
[a]d-20: +110.7pm2deg (C=1.617, CHCl3) (Me ester)(Ref. 0116)









[0116]
595
7,12-Dioxochol-5-en-24-oic Acid
 BBA0645
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

106-108degC(Ref. 0131)
lmax (e): 237(9150) nm(Ref. 0131)









[0131]
596
3,7,12-Trioxo-5b-chol-1-en-24-oic Acid
 BBA0646
Takashi Iida
C24H32O5 400.508 Download ChemDraw structure file

160-164degC(Ref. 0131)
lmax (e): 228(6200) nm(Ref. 0131)









[0131]
597
3,7,12-Trioxochol-4-en-24-oic Acid
 BBA0647
Takashi Iida
C24H32O5 400.508 Download ChemDraw structure file

168-171degC(Ref. 0131)
lmax (e): 278(8000) nm(Ref. 0131)









[0131]
598
3,7,12-Trioxochol-5-en-24-oic Acid
 BBA0648
Takashi Iida
C24H32O5 400.508 Download ChemDraw structure file

163-166degC(Ref. 0131)
lmax (e): 277(9300) nm(Ref. 0131)









[0131]
599
3,7,12-Trioxochola-1,4-dien-24-oic Acid
 BBA0649
Takashi Iida
C24H30O5 398.492 Download ChemDraw structure file

175-178degC(Ref. 0131)
lmax (e): 233(9100) nm(Ref. 0131)









[0131]
600
3,7,12-Trioxochola-1,5-dien-24-oic Acid
 BBA0650
Takashi Iida
C24H30O5 398.492 Download ChemDraw structure file

178-180degC(Ref. 0131)
lmax (e): 237(12800) nm(Ref. 0131)









[0131]
601
3a,12b-Dihydroxy-5b-chol-9(11)-en-24-oic Acid
 BBA0651
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

107degC(Ref. 0135/0250)
105.5-107degC (Me ester-3,12-diacetate)(Ref. 0105)
100-101degC (Me ester-3-acetate)(Ref. 0250)
[a]D: +28deg (C=1.0, MeOH)(Ref. 0135/0250)
[a]D: +47pm2deg (30.4mg in 3ml of MeOH) (Me ester-3-acetate)(Ref. 0135/0250)

Me ester-3,12-diacetate m/z: 488(M+), 428(M-AcOH, 19%), 413(M-AcOH-CH3, 12%), 386(16%), 368(M-2AcOH, 15%), 353(M-2AcOH-CH3, 10%), 314(M-2AcOH-54, 27%), 313((M-AcOH-SC, 100%), 286(4%), 253(M-2AcOH-SC, 50%), 226(13%)(Ref. 0105)







[0105] / [0135] / [0250]
602
3a,11a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0652
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

147degC(Ref. 0135)
[a]D: +22deg (EtOH)(Ref. 0135)









[0135]
603
12a-Hydroxy-3-oxo-5b-chol-9(11)-en-24-oic Acid
 BBA0653
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

[a]d-20: +103deg (C=1.0, CHCl3) (Me ester-3-acetate)(Ref. 0078)
Me ester-3-acetate: nmaxcm-1: 1740, 1245, 1019 (OCOMe), 1732, 1437, 1175(COOMe), 1715 (>C=O), 1654, 1646, 3060 (>C=C<)(Ref. 0078)
Me ester-3-acetate 1H-NMR(CDCl3) d: 18-Me 0.63(s), 19-Me 1.15(s), OCOMe 2.03(s), COOMe 3.65(s), 12b-H 4.97(d, J, 6.0), 11-H 5.81(d, J, 6.0)(Ref. 0078)
Me ester-3-acetate m/z: 444(M+)(Ref. 0078)







[0078]
604
3a,11a,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0654
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

173-175degC, (Me ester ; mp, 133-135degC)(Ref. 0222/0261)
[a]d-23: +26.7deg (C=0.96, EtOH)(Ref. 0261)
[a]14D: +16.4pm2deg (C=1.640, CHCl3) (Me ester)(Ref. 0222)
[a]d-23: +28.4deg (C=0.875, EtOH) (Me ester)(Ref. 0261)









[0222] / [0261]
605
3a,11a,12b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0655
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

162-164degC(Ref. 0261)186-187degC(Me ester-triacetate)(Ref. 0261)
[a]d-23: +46.9deg (C=0.78, EtOH), [a]d-23: +64.5deg (C=0.31, EtOH) (Me ester-triacetate)(Ref. 0261)









[0261]
606
3a,11b,12a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0656
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

145-147degC(Ref. 0001/0087)
176-177degC(Ref. 0261)
[a]D: +54deg (EtOH)(Ref. 0001/0087)
a]d-24: +42.9deg (C=0.97, EtOH)(Ref. 0261)









[0001] / [0087] / [0261]
607
3a,11b,12b-Trihydroxy-5b-cholan-24-oic Acid
 BBA0657
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

177degC(Ref. 0001)
[a]D: +43deg (EtOH)(Ref. 0001)









[0001]
608
3a,12a-Dihydroxy-11-oxo-5b-cholan-24-oic Acid
 BBA0658
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

141-145degC(Ref. 0087)
[a]d-26: +63.6pm1.5deg (C=1.222, CHCl3)(Ref. 0087)
lmax (EtOH) (loge): 313(1.69) nm(Ref. 0087)









[0087]
609
3,7,12-trioxo-5a-cholan-24-oic Acid
 BBA0659
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

232-233degC(Ref. 0038/0237)
198-199degC (Me ester)(Ref. 0013/0237)
[a]d-25: +19.8pm1deg (C=0.36, MeOH) (Ref. 0038/0237)
[a]d-25: +29.0pm1deg (C=1.0, CHCl3) (Me ester)(Ref. 0013/0237)
Me ester: nmaxcm-1: 1736, 1706, 1282, 811(Ref. 0013)
Me ester 1H-NMR(CDCl3; 90MHz) d: 18-Me 1.07(s), 19-Me 1.37(s), 21-Me 0.85(d)(Ref. 0008/0065)
Me ester 13C-NMR(CDCl3 ; 22.53MHz) d : C-1 37.2, C-2 36.4, C-3 207.5, C-4 43.8, -C5 46.9, C-6 45.4, C-7 208.2, C-8 49.0, C-9 56.2, C-10 36.6, C-11 38.6, C-12 211.8, C-13 56.6, C-14 51.5, -15 25.2, C-16 27.5, C-17 45.6, C-18 11.8, C-19 10.7, C-20 35.4, C-21 18.5, C-22 31.2, C-23 30.4, C-24 174.4, C-25 51.3(Ref. 0065)
Me ester (70eV) m/z: 416(M+, 41%), 401(M-CH3, 3%), 398(M-H2O, 38%), 384(M-32, 6%), 380(M-2H2O, 1%), 367(M-H2O-31, 8%), 343(M-73, 16%), 301(M-SC, 37%), 283(M-H2O-SC, 25%), 275(M-SC-26, 6%), 274(M-SC-part of ringD, 16%), 265(M-2H2O-SC, 6%), 261(M-SC-40, 100%), 260(M-SC-41, 2%), 259(M-H2O-SC-ringD, 7%)(Ref. 0009)







[0008] / [0009] / [0013] / [0038] / [0065] / [0237]
610
3-Oxo-5b-chol-8-en-24-oic Acid
 BBA0660
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

122degC (Me ester)(Ref. 0104)
[a]d-20: +22deg (CHCl3) (Me ester)(Ref. 0104)
Me ester: lmax (EtOH) (e): 211(2420) nm(Ref. 0104)
Me ester: nmaxmcm-1: 1740, 1715(C=O)(Ref. 0104)









[0104]
611
3-Oxo-5b-chol-8(14)-en-24-oic Acid
 BBA0661
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

104degC (Me ester)(Ref. 0104)
[a]d-19: +68deg (CHCl3) (Me ester)(Ref. 0104)
Me ester: lmax (EtOH) (e): 214(5190) nm(Ref. 0104)
Me ester: nmaxmcm-1: 1730, 1710(C=O)(Ref. 0104)









[0104]
612
3-Oxo-5b-chol-9(11)-en-24-oic Acid
 BBA0662
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

106degC (Me ester)(Ref. 0104)
[a]d-21: +33deg (CHCl3) (Me ester)(Ref. 0104)
Me ester: lmax (EtOH) (e): 211(2200) nm(Ref. 0104)
Me ester: nmaxmcm-1: 1738, 1720(C=O), 825(=C-H)(Ref. 0104)









[0104]
613
3-Oxo-5b-chol-6-en-24-oic Acid
 BBA0663
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

125degC (Me ester)(Ref. 0104)
[a]d-22: -52deg (CHCl3) (Me ester)(Ref. 0104)
Me ester:lmax (EtOH) (e): 214(320) nm(Ref. 0104)
Me ester: nmaxmcm-1: 1743, 1717(C=O), 740(=C-H)(Ref. 0104)









[0104]
614
3a-Hydroxy-12-oxo-5b-chol-8-en-24-oic Acid
 BBA0664
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

131degC (Me ester-3-acetate)(Ref. 0104)
[a]d-22:+138deg (CHCl3) (Me ester-3-acetate)(Ref. 0104)
Me ester-3-acetate: lmax (EtOH) (e): 213(3980) nm(Ref. 0104)
Me ester-3-acetate: nmaxmcm-1: 1734, 1705(C=O), 1255(C-O-C)(Ref. 0104)









[0104]
615
3a-Hydroxy-12-oxo-5b-chol-8(14)-en-24-oic Acid
 BBA0665
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

98degC (Me ester-3-acetate)(Ref. 0104)
[a]d-19: +55deg (CHCl3) (Me ester-3-acetate)(Ref. 0104)
Me ester-3-acetate: lmax (EtOH) (e): 215(5270) nm(Ref. 0104)
Me ester-3-acetate: nmaxmcm-1: 1730, 1720(C=O), 1245(C-O-C)(Ref. 0104)









[0104]
616
3,12-Dioxo-5b-chol-8(14)-en-24-oic Acid
 BBA0666
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

120degC (Me ester)(Ref. 0104)
[a]d-18: +14deg (CHCl3) (Me ester)(Ref. 0104)
Me ester: lmax (EtOH) (e): 215(5940) nm(Ref. 0104)
Me ester: nmaxmcm-1: 1738,1705(C=O), 780(=C-H)(Ref. 0104)









[0104]
617
3a,7a,12b-Trihydroxy-11-oxo-5b-cholan-24-oic Acid
 BBA0667
Takashi Iida
C24H38O6 422.555 Download ChemDraw structure file


Me ester-7-acetate (12eV) m/z: 478(M+, 25%), 463(M-CH3, 10%), 460(M-H2O, 14%), 445(M-CH3-H2O, 14%), 442(M-2H2O, 9%), 418(M-AcOH, 25%), 400(M-H2O-AcOH, 69%), 387(M-AcOH-CH3O, 34%), 386(M-AcOH-MeOH, 15%), 385(M-H2O-AcOH-CH3, 46%), 382(M-2H2O-AcOH, 49%), 371(M-AcOH-MeOH-CH3O, 34%), 369(M-H2O-AcOH-CH3O, 22%), 367(M-2H2O-AcOH-CH3, 25%), 345(M-H2O-C6H11O2, 19%), 327(M-H2O-AcOH-C3H5O2, 100%), 309(M-2H2O-AcOH-C3H5O2, 29%), 285(M-H2O-AcOH-C6H11O2, 51%), 267(M-2H2O-AcOH-C6H11O2, 67%), 259(30%), 257(19%), 245(24%), 241(25%), 229(39%)(Ref. 0233)
Me ester-3,7,12-triacetate (70eV) m/z: 562(M, 10%), 502(M-AcOH, 15%), 442(M-2AcOH, 75%), 520(9%), 487(30%), 460(11%), 427(20%), 400(25%), 382(100%), 367(60%), 267(90%)(Ref. 0231)







[0231] / [0233]
618
3a-Hydroxy-12-oxo-5b-chola-7,9(11)-dien-24-oic Acid
 BBA0668
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

155-157degC (Me ester-3-acetate)(Ref. 0229)
[a]D: +250deg (C=0.9CHCl3) (Me ester-3-acetate)(Ref. 0229)

Me ester-3-acetate (12eV) m/z: 442(M+, 9%), 427(M-CH3, 3%), 424(M-H2O, 1%), 411(M-CH3O, 7%), 382(M-AcOH, 31%), 367(M-AcOH-CH3, 7%), 364(M-H2O-AcOH, 3%), 340(M-AcOH-CH2CO, 4%), 335(M-AcOH-CH3-MeOH, 3%), 328(M-AcOH-C4H6, 4%), 345(M-H2O-C6H11O2, 19%), 327(M-H2O-AcOH-C3H5O2, 100%), 309(M-AcOH-CH2CO2CH3, 3%), 295(M-AcOH-C4H7O2, 4%), 287(M-C9H15O2, 10%), 267(M-AcOH-C6H11O2, 16%), 249(M-H2O-AcOH-C6H11O2, 0%), 241(M-H2O-AcOH-C4H7O2-C4H6, 21%), 227(M-C9H15O2-AcOH),
185(M-C9H15O2-AcOH-CH2CO, 100%)(Ref. 0233)







[0229] / [0233]
619
3a-Hydroxy-12-oxo-5a-cholan-24-oic Acid
 BBA0669
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file


The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)







[0007]
620
11b,12b-Dihydroxy-5b-cholan-24-oic Acid
 BBA0670
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

211-214degC, (Me ester; mp, 103-104degC, Me ester-11.12-diacetate; mp, 108-110degC)(Ref. 0220)
[a]d-11: +3.2pm1deg (C=1.863, dioxane), [a]16D: +12.2pm1deg (C=1.973, MeOH) (Me ester), [a]13D: +1.5pm1deg (C=1.94, acetate)(Me ester-11,12-diacetate)(Ref. 0220)









[0220]
621
3a-Hydroxy-12-oxo-5b-chol-6-en-24-oic Acid
 BBA0671
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

200-201degC(Ref. 0132)
[a]d-22: +84.5pm1deg(Ref. 0132)









[0132]
622
5b-Chola-3,11-dien-24-oic Acid
 BBA0672
Takashi Iida
C24H36O2 356.541 Download ChemDraw structure file

83.5-84.5degC (Me ester)(Ref. 0069)
[a]d-25: +33.4deg (Me ester)(Ref. 0069)









[0069]
623
3b-Hydroxy-11-oxo-5b-chol-8-en-24-oic Acid
 BBA0673
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

148.1-148.8degC (Me ester-3-acetate)(Ref. 0055)
[a]d-23: +21.4pm2deg (2.33%,CHCl3) (Me ester-3-acetate)(Ref. 0055)
Me ester-3-acetate: lmax (EtOH) (loge): 255(3.95) nm(Ref. 0055)
Me ester-3-acetate: nmaxNujolm: 5.70-5.75, 6.04, 6.23(Ref. 0055)









[0055]
624
3a-Hydroxy-11,12-dioxo-5b-cholan-24-oic Acid
 BBA0674
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

208-211degC (Me ester-3-formate)(Ref. 0077)
[a]d-25: +124deg (C=1.0, CHCl3) (Me ester-3-formate)(Ref. 0077)









[0077]
625
7a-Hydroxy-3,12-dioxochola-1,4-dien-24-oic Acid
 BBA0675
Takashi Iida
C24H34O4 386.524 Download ChemDraw structure file

245-246degC (Me ester-7-acetate)(Ref. 0121)
Me ester-7-acetate: lmax (e): 238.2(21900) nm(Ref. 0121)
Me ester-7-acetate: nmaxmcm-1: 1700, 1725(C=O), 1600, 1620, 1660(D1.4-3-OXO), 1018, 1168, 1230(acetate)(Ref. 0121)
Me ester-7-acetate 1H-NMR(CDCl3; 90MHz) d: 21-Me 0.87(d), 7a-OCOMe 1.12(s), COOMe 3.66(s), 7b-H 5.12(m), 4-H 6.05(s), 2-H 6.29(dd, J, 9.9, 1.8), 1-H 6.90(d, J, 9.9)(Ref. 0121)








[0121]
626
3a-Hydroxy-15-oxo-5b-chol-8-en-24-oic Acid
 BBA0676
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

112-114degC (Me ester-3-acetate)(Ref. 0107)
[a]D: +146.6deg (C=0.545, dioxane) (Me ester-3-acetate)(Ref. 0107)
Me ester-3-acetate: lmax (EtOH) (e): 261(11252) nm(Ref. 0107)
Me ester-3-acetate: nmaxmcm-1: 1735, 1705, 1627, 1365, 1240, 1030(Ref. 0107)
Me ester-3-acetate 1H-NMR(CDCl3) d: 18-Me 0.98(s), 19-Me 0.84(s), 21-Me 1.025(d), 3a-OCOMe 2.02(s), COOMe 3.67(s), 7-H 4.08(m), 3b-H 4.78(m)(Ref. 0107)








[0107]
627
12a-Hydroxy-3-oxochola-1,4,6-trien-24-oic Acid
 BBA0677
Takashi Iida
C24H32O4 384.508 Download ChemDraw structure file

Me ester-12-acetate 1H-NMR(CDCl3; 500MHz) d: 18-Me 0.865(s), 19-Me 1.185(s), 21-Me 0.818(d), 1-H 6.942(d, J, 10.0), 2-H 6.053(dd, J, 9.5, 1.4), 4-H 6.012(s), 6-H 6.254(dd, J, 10.0, 3.0), 7-H 6.229(dd, J, 10.0, 2.0), 12b-H 5.148(t, J, 2.5), COOMe 3.664(s), 12a-OCOMe 2.027(s)(Ref. 0071)
Me ester-12-acetate 13C-NMR(CDCl3; 125.65MHz) d: C-1 152.0, C-2 128.4, C-3 186.0, C-4 124.0, C-5 161.8, C-6 127.8, C-7 137.6, C-8 38.0, C-9 42.2, C-10 40.5, C-11 26.3, C-12 74.7 C-13 45.5, C-14 46.8, C-15 22.9, C-16 27.1, C-17 47.5, C-18 12.2, C-19 20.4, C-20 34.6, C-21 17.4, C-22 30.8, C-23 30.9, C-24 174.2, C-25 51.4(Ref. 0251)








[0071] / [0251]
628
3b-Hydroxy-7-oxochol-5-en-24-oic Acid
 BBA0678
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

Me ester-3-acetate 1H-NMR(CDCl3; 500MHz) d: 18-Me 0.649(s), 19-Me 1.174(s), 21-Me 0.899(d), 3b-H 4.679(brm), 6-H 5.670(s), COOMe 3.630(s), 3b-OCOMe 2.018(s)(Ref. 0071)








[0071]
629
7a,12a-Dihydroxy-5b-chol-2-en-24-oic Acid
 BBA0679
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

Me ester 1H-NMR(CDCl3; 500MHz) d: 18-Me 0.574(s), 19-Me 0.839(s), 21-Me 0.859(d), 2-H 5.368(brm), 3-H 5.486(brm), 7b-H 3.773(m), 12b-H 3.829(t, J, 2.1), COOMe 3.543(s)(Ref. 0071)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 33.3, C-2 122.9, C-3 127.4, C-4 29.6, C-5 38.6, C-6 35.5, C-7 68.5, C-8 39.7, C-9 27.4, C-10 34.1, C-11 29.1, C-12 72.8, C-13 46.5, C-14 42.0, C-15 23.2, C-16 27.4, C-17 46.9, C-18 12.5, C-19 22.8, C-20 35.1, C-21 17.2, C-22 30.8, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0244)








[0071] / [0244]
630
3,12-Dioxochola-4,6-dien-24-oic Acid
 BBA0680
Takashi Iida
C24H32O4 384.508 Download ChemDraw structure file

205-208degC(Ref. 0239)168-170degC(Me ester)(Ref. 0239/0252/0260)
lmax (EtOH) (loge): 280.5(4.42) mm(Ref. 0260)
Me ester: nmaxcm-1: 1580, 1612(4,6-diene), 1653(3-ketone), 1705(12-ketone), 1720(carboxy)(Ref. 0252)
nmaxm: 6.00, 6.18, 6.30(4-ene-3-ketone), 5.85(ester), 5.81(ester)(Ref. 0260)
Me ester 1H-NMR(CDCl3; 220MHz) d: 18-Me 0.88(s), 19-Me 1.20(s), 21-Me 1.13(s), COOMe 3.68(s), 4-H 5.73(s), 6-H 6.14(s), 7-H 6.14(s)(Ref. 0004/0252)
Me ester m/z: 398(M, 100%), 283(M-SC, 34%), 136(4,6-diene-3-one, 33%)(Ref. 0252)


A microbiological degradation product of cholic acid by Streptomyces rubescens.(Ref. 0239)
A bacterial degradation product of cholic acid by Pseudomonas sp. N.C.I.B. 10590.(Ref. 0252)
A microbiological degradation product of dehydrocholic acid by Corynebacterium sp.(Ref. 0260)




[0004] / [0239] / [0252] / [0260]
631
11b-Hydroxy-5b-cholan-24-oic Acid
 BBA0681
Takashi Iida
C24H40O3 376.573 Download ChemDraw structure file

85-86degC(Ref. 0001)
[a]D: +50deg (acetone)(Ref. 0001)









[0001]
632
12a-Hydroxy-7-oxo-5b-cholan-24-oic Acid
 BBA0682
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

176degC(Ref. 0001)









[0001]
633
12b-Hydroxy-3-oxochol-4-en-24-oic Acid
 BBA0683
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

230-235degC, (Me ester ; mp, 150-152degC)(Ref. 0001)
[a]d-17: +80.9deg (C=0.606, acetone)(Ref. 0001)









[0001]
634
3a,12a-Dihydroxy-5b-chola-7,9(11)-dien-24-oic Acid
 BBA0684
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

138-138.5degC (Me ester-3-acetate)(Ref. 0229)
[a]D: +286deg (C=0.7, CHCl3) (Me ester-3,12-diacetate), [a]D: +163deg (C=2.9, CHCl3) (Me ester-3-acetate)(Ref. 0229)
Me ester-3,12-diacetate: lmax (EtOH) (e): 240(12600), 249(14400), 258(11200) nm(Ref. 0229)
Me ester-3-acetate: lmax (EtOH) (e): 238(13800), 247(16300), 255(12300) nm(Ref. 0229)
Me ester-3,12-diacetate: nmaxcm-1: 1200(ester), 1610(ethylene), 1725(ester)(Ref. 0229)
Me ester-3-acetate: nmaxcm-1: 1210(ester), 1615(ethylene), 1740(ester), 3650(OH)(Ref. 0229)
Me ester-3,12-diacetate 1H-NMR (CDCl3) d: 18-Me 0.55, 19-Me 1.02, 3a-OCOMe 1.98, 7-H 5.42, COOMe 3.65, 3b-H 4.70(br), 12b-H 5.08(d, J, 6.0), 11-H 5.80(d, J, 6.0)(Ref. 0229)
Me ester-3-acetate 1H-NMR (CDCl3) d: 18-Me 0.47, 19-Me 1.00, 3a-OCOMe 1.98, 7-H 5.40, COOMe 3.63, 3b-H 4.62(b), 12b-H 4.00(d, J, 6.0), 11-H 5.77(d, J, 6.0)(Ref. 0229)








[0229]
635
3a,12b-Dihydroxy-5b-chola-7,9(11)-dien-24-oic Acid
 BBA0685
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

98-100degC (Me ester-3,12-diacetate)(Ref. 0229)
105-106degC (Me ester-3-acetate)(Ref. 0229)
[a]D: +49deg (C=1.7, CHCl3) (Me ester-3,12-diacetate), [a]D: +123deg (C=1.7, CHCl3) (Me ester-3-acetate)(Ref. 0229)
Me ester-3,12-diacetate: lmax (EtOH) (e): 238(14100), 247(16000), 255(11500) nm(Ref. 0229)
Me ester-3-acetate: lmax (EtOH) (e): 241(15600), 247(16900), 256(11700) nm(Ref. 0229)
Me ester-3-acetate: nmaxcm-1: 1210(ester), 1615(ethylene), 1740(ester), 3650(OH)(Ref. 0229)
Me ester-3,12-diacetate 1H-NMR (CDCl3) d: 18-Me 0.61, 19-Me 1.02, 3a-OCOMe 1.95, 7-H 5.23, COOMe 3.63, 3b-H 4.63(br), 12a-H 5.13(br), 11-H 5.39(Ref. 0229)
Me ester-3-acetate 1H-NMR (CDCl3) d: 18-Me 0.53, 19-Me 1.03, 3a-OCOMe 1.95, 7-H 5.23, COOMe 3.63, 3b-H 4.68(br), 12a-H 4.22(br), 11-H 5.30(Ref. 0229)








[0229]
636
3a,7a,12a-Trihydroxy-5b-chol-9(11)-en-24-oic Acid
 BBA0686
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

172-174degC (Me ester-3,7-diacetate)(Ref. 0229)
[a]D: +169deg (C=1.5, CHCl3) (Me ester-3,7,12-triacetate), [a]D: +71deg (C=1.5, CHCl3) (Me ester-3,7-diacetate)(Ref. 0229)
Me ester-3,7,12-triacetate 1H-NMR (CDCl3) d: 18-Me 0.63, 19-Me 1.10, 3a- and 7a-OCOMe 2.02 and 2.08, COOMe 3.65, 3b-H 4.63(br), 7b-H 5.12, 12b-H 5.00(d, J, 6.0), 11-H 5.85(d, J, 6.0)(Ref. 0229)
Me ester-3,7-diacetate 1H-NMR (CDCl3) d: 18-Me 0.57, 19-Me 1.12, 3a- and 7a-OCOMe 1.98, COOMe 3.65, 3b-H 4.57(br), 7b-H 5.07(br), 12b-H 3.82(d, J, 6.0), 11-H 5.75(d, J, 6.0)(Ref. 0229)








[0229]
637
3a,7a,12b-Trihydroxy-5b-chol-9(11)-en-24-oic Acid
 BBA0687
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

104-106degC (Me ester-3,7,12-triacetate)(Ref. 0229)
135-137degC (Me ester-3,7-diacetate)(Ref. 0229)
[a]D: 0deg (C=1.6, CHCl3) (Me ester-3,7,12-triacetate), [a]D: +31deg (C=1.1, CHCl3) (Me ester-3,7-diacetate)(Ref. 0229)
Me ester-3,7,12-triacetate 1H-NMR (CDCl3) d: 18-Me 0.73, 19-Me 1.12, 3a- and 7a-OCOMe 1.98, 12a-OCOMe 2.08, COOMe 3.66, 3b-H 4.60(br), 7b-H 5.08(br), 12a-H 5.17(br), 11-H 5.35(br)(Ref. 0229)
Me ester-3,7-diacetate 1H-NMR (CDCl3) d: 18-Me 0.63, 19-Me 1.10, 3a- and 7a-OCOMe 1.98, COOMe 3.64, 3b-H 4.55(br), 7b-H 5.03(br), 12a-H 4.08(br)(Ref. 0229)








[0229]
638
3b,19-Dihydroxychol-5-en-24-oic Acid
 BBA0688
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

123-124degC (Me ester-3-acetate)(Ref. 0236)
Me ester-3-acetate: nmaxcm-1: 1260, 1740, 3520(Ref. 0236)
Me ester-3-acetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.72(s), 3b-OCOMe 2.04(s), COOMe 3.65(s), 19-CH2 3.64 and 3.84(dd, J, 10.0), 3a-H 4.64(br), 6-H 5.76(t)(Ref. 0236)








[0236]
639
3a,12a-Dihydroxy-6-oxo-5b-chol-7-en-24-oic Acid
 BBA0689
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

128-130degC (Me ester-3,12-diacetate)(Ref. 0230)
Me ester-3,12-diacetate: lmax (loge): 243(4.28) nm(Ref. 0230)
Me ester-3,12-diacetate: nmaxcm-1: 1630, 1660(C=C-C=O), 1720(COOMe), 1250, 1740(OCOMe)(Ref. 0230)
Me ester-3,12-diacetate 1H-NMR (CDCl3) d: 18-Me 0.71(s), 19-Me 0.93(s), 3a- and 12a-OCOMe 2.00, 2.17(s), 23-H2 2.8(m), COOMe 3.66(s), 3b-H 4.69, 12b-H 5.26, 7-H 5.69(Ref. 0230)
Me ester-3,12-diacetate m/z: 502(M, 9%), 442(M-AcOH, 62%), 382(M-2AcOH, 100%), 327(M-AcOH-C6H11O2, 36%), 267(M-2AcOH-C6H11O2, 98%)(Ref. 0230)







[0230]
640
6a-Hydroxy-3-oxochol-4-en-24-oic Acid
 BBA0690
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

Me ester 1H-NMR(CDCl3) d: 18-Me 0.69(s), 19-Me 1.18(s), 21-Me 0.92(d), 6b-H 4.35(m), COOMe 3.67(s), 4-H 6.16(s)(Ref. 0004)








[0004]
641
22(E)-12a-Hydroxy-3-oxochola-1,4,22-trien-24-oic Acid
 BBA0691
Takashi Iida
C24H32O4 384.508 Download ChemDraw structure file

Me ester 1H-NMR(CDCl3) d: 18-Me 0.82(s), 19-Me 1.23(s), 21-Me 1.15(d), COOMe 3.73(s), 12b-H 4.06(m), 23-H 5.74(d, J, 16.0), 4-H 6.06(brs), 2-H 6.02(dd, J, 2.0, 10.0), 22-H 6.85(dd, J, 9.0, 16.0), 1-H 7.00(d, J, 10.0)(Ref. 0004)








[0004]
642
3-Oxo-5b,14b-chol-8-en-24-oic Acid
 BBA0692
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

140-142degC(Ref. 0240)
[a]D: +102.3deg(Ref. 0240)
nmaxcm-1: 1710(C=O)(Ref. 0240)
Me ester: nmaxcm-1: 1710, 1720(C=O)(Ref. 0240)









[0240]
643
2b,7a,12a-Trihydroxy-3-oxo-5b-cholan-24-oic Acid
 BBA0693
Takashi Iida
C24H38O6 422.555 Download ChemDraw structure file

168-170degC (Me ester-2,7,12-triacetate)(Ref. 0218)
Me ester-2,7,12-triacetate 1H-NMR(CDCl3; 100MHz) d: 18-Me 0.76, 19-Me 1.03, 2b,7a- and 12a-OCOMe 2.08, 2.10, 2.12(each s), COOMe 3.65(Ref. 0218)
Me ester-2,7,12-triacetate (70eV) m/z: 562(M+)(Ref. 0218)







[0218]
644
(22Z)-3a-Hydroxy-7-oxo-5b-chol-22-en-24-oic Acid
 BBA0694
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file





Primary bile acid in mountain paca.(Ref. 0102)




[0102]
645
3a,7a,15a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0695
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file





Primary bile acid in marsupials.(Ref. 0102)




[0102]
646
3a,5b-Dihydroxycholan-24-oic Acid
 BBA0696
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file

167-168degC (Me ester-3-acetate)(Ref. 0226)
Me ester-3-acetate 1H-NMR(CDCl3) d: 18-Me 0.61(s), 19-Me 0.87(s), 21-Me 0.89(d), 3a-OCOMe 2.00(s), COOMe 3.64(s), 3b-H 5.05(tt, J, 11.1 4.7)(Ref. 0226)
Me ester-3-acetate 13C-NMR (CDCl3; 125MHz) d: C-1 29.2, C-2 26.0, C-3 71.4, C-4 38.0, C-5 75.3, C-6 36.7, C-7 28.5, C-8 34.8, C-9 43.1, C-10 39.5, C-11 21.0, C-12 39.7, C-13 42.4, C-14 56.4, C-15 24.0, C-16 28.0, C-17 55.6, C-18 11.8, C-19 16.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.8, C-24 174.9, C-25 51.4(Ref. 0228)
Me ester-3-acetate m/z: 430(5%), 388(17%), 370(100%), 355(24%), 334(99%), 315(14%), 273(36%), 255(55%), 228(26%), 213(68%)(Ref. 0228)







[0226] / [0228]
647
3a,7a-Dihydroxy-12-oxo-5b-chol-9(11)-en-24-oic Acid
 BBA0697
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

156-158degC (Me ester-3,7-diacetate)(Ref. 0229)
[a]D: +89deg (C=1.9, CHCl3) (Me ester3,7-diacetate)(Ref. 0229)









[0229]
648
3a,7a,17a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0698
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

Me ester-3,7-diacetate: nmaxcm-1: 1026, 1069, 1367, 1382, 1729, 2872, 2932, 3606(Ref. 0228)
Me ester-3,7-diacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.73(s), 21-Me 0.91(d), 19-Me 0.94(s), 3a- and 7a-OCOMe 2.03 and 2.06(each s), 23-H 2.25(m), 23'-H 2.43(m), COOMe 3.67(s), 3b-H 4.59(m), 7b-H 4.91(m)(Ref. 0228)
Me ester-3,7-diacetate 13C-NMR (CDCl3; 125MHz) d: C-1 34.8, C-2 26.6, C-3 74.1, C-4 34.5, C-5 40.9, C-6 31.2, C-7 71.0, C-8 38.1, C-9 33.8, C-10 34.7, C-11 20.4, C-12 32.0, C-13 47.6, C-14 44.9, C-15 22.8, C-16 37.8, C-17 86.0, C-18 14.0, C-19 22.6, C-20 39.1, C-21 13.4, C-22 27.3, C-23 32.0, C-24 174.5, C-25 51.4(Ref. 0228)
Me ester-3,7-diacetate m/z: 446(5%), 428(15%), 413(17%), 386(6%), 373(13%), 368(16%), 353(34%), 313(41%), 288(17%), 281(31%), 271(6%), 253(100%), 228(56%), 215(20%), 213(18%), 171(50%)(Ref. 0228)







[0228]
649
3a,7a,11a-Trihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0699
Takashi Iida
C24H38O6 422.555 Download ChemDraw structure file


Me ester-3,7,11-triacetate (70eV) m/z: 562(M, 4%), 502(M-AcOH, 72%), 442(M-2AcOH, 51%), 531(5%), 520(4%), 487(5%), 484(6%), 471(5%), 427(9%), 424(10%), 400(12%), 382(93%), 367(33%), 364(21%), 327(35%), 267(100%), 241(76%), 227(100%)(Ref. 0231)







[0231]
650
7a-Hydroxy-3,12-dioxochol-4-en-24-oic Acid
 BBA0700
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

248-252degC, (Me ester ; mp, 172-174degC)(Ref. 0239/0260)
lmax (EtOH) (loge): 241(4.21) mm(Ref. 0260)
nmaxm: 6.04, 6.18(4-ene-3-ketone), 5.88(12-ketone), 5.82(carbonyl), 3.02(hydroxyl)(Ref. 0260)




A microbiological degradation product of cholic acid by Streptomyces rubescens.(Ref. 0239)
A microbiological degradation product of dehydrocholic acid by Corynebacterium sp.(Ref. 0260)




[0239] / [0260]
651
3a,7b,14a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0701
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

Me ester-3,7-diacetate: nmaxcm-1: 1027, 1048, 1366, 1729, 2876, 2936, 3609(Ref. 0228)
Me ester-3,7-diacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.79(s), 21-Me 0.90(d), 19-Me 0.99(s), 3a- and 7b-OCOMe 2.00 and 2.03(each s), 9a-H 2.14(td, J, 12.0, 4.5), 23-H 2.25(m), 23'-H 2.39(m), COOMe 3.67(s), 3b-H 4.67(m), 7a-H 5.15(td, J, 11.0, 5.5)(Ref. 0228)
Me ester-3,7-diacetate 13C-NMR (CDCl3; 125MHz) d: C-1 34.5, C-2 26.1, C-3 73.5, C-4 32.7, C-5 41.9, C-6 32.9, C-7 69.4, C-8 43.3, C-9 32.1, C-10 34.0, C-11 19.9, C-12 31.8, C-13 47.6, C-14 83.9, C-15 34.8, C-16 27.2, C-17 49.4, C-18 15.5, C-19 22.7, C-20 34.9, C-21 18.2, C-22 30.9, C-23 31.0, C-24 174.8, C-25 51.4(Ref. 0228)
Me ester-3,7-diacetate m/z: 446(2%), 428(10%), 386(28%), 368(23%), 353(13%), 313(34%), 281(6%), 271(10%), 253(36%), 212(82%), 174(41%),97(81%), 96(100%)(Ref. 0228)







[0228]
652
3a,7b,17a-Trihydroxy-5b-cholan-24-oic Acid
 BBA0702
Takashi Iida
C24H40O5 408.571 Download ChemDraw structure file

Me ester-3,7-diacetate: nmaxcm-1: 1025, 1366, 1729, 2876, 2938, 3607(Ref. 0228)
Me ester-3,7-diacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.76(s), 21-Me 0.90(d), 19-Me 0.98(s), 3a- and 7b-OCOMe 1.98 and 2.03(each s), 23-H 2.26(m), 23'-H 2.44(m), COOMe 3.68(s), 3b-H 4.67(m), 7a-H 4.81(td, J, 10.7, 5.5)(Ref. 0228)
Me ester-3,7-diacetate 13C-NMR (CDCl3; 125MHz) d: C-1 34.4, C-2 26.2, C-3 73.7, C-4 32.7, C-5 41.9, C-6 32.7, C-7 73.4, C-8 40.0, C-9 38.9, C-10 33.8, C-11 20.8, C-12 32.2, C-13 48.4, C-14 49.8, C-15 24.7, C-16 38.4, C-17 84.9, C-18 14.4, C-19 23.0, C-20 38.9, C-21 13.4, C-22 27.4, C-23 32.0, C-24 174.5, C-25 51.4(Ref. 0228)
Me ester-3,7-diacetate m/z: 446(40%), 428(8%), 413(15%), 386(34%), 368(23%), 353(27%), 313(73%), 288(31%), 281(13%), 271(24%), 253(59%), 228(100%), 215(27%), 213(24%), 176(76%)(Ref. 0228)







[0228]
653
3a,5b,7a,12a-Tetrahydroxycholan-24-oic Acid
 BBA0703
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

87-89degC (Me ester-3,7,12-triacetate)(Ref. 0228)
Me ester-3,7,12-triacetate: nmaxcm-1: 1030, 1368, 1379, 1730, 2872, 2921, 3608(Ref. 0228)
Me ester-3,7,12-triacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.73(s), 21-Me 0.82(d), 19-Me 0.90(s), 3a-, 7a- and 12a-OCOMe 2.05, 2.11 and 2.14(each s), 23-H 2.22(m), 4a-H 2.24(t, J, 13.0), 23'-H 2.35(m), COOMe 3.67(s), 7b-H 4.96(m), 3b-H 5.02(m), 12b-H 5.11(m)(Ref. 0228)
Me ester-3,7,12-triacetate 13C-NMR (CDCl3; 125MHz) d: C-1 29.1, C-2 26.2, C-3 70.8, C-4 40.6, C-5 74.2, C-6 40.7, C-7 70.5, C-8 36.9, C-9 31.7, C-10 39.2, C-11 25.7, C-12 75.0, C-13 44.8, C-14 43.0, C-15 22.7, C-16 27.0, C-17 47.2, C-18 12.0, C-19 15.6, C-20 34.5, C-21 17.3, C-22 30.8, C-23 30.7, C-24 174.7, C-25 51.5(Ref. 0228)
Me ester-3,7,12-triacetate m/z: 444(31%), 426(41%), 384(90%), 366(80%), 351(35%), 330(81%), 329(71%), 311(32%), 269(100%), 251(78%), 209(36%)(Ref. 0228)







[0228]
654
(23R)-3a,5b,7a,23-Tetrahydroxycholan-24-oic Acid
 BBA0704
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

171-173degC (Me ester-3,7,23-triacetate)(Ref. 0228)
Me ester-3,7,23-triacetate: nmaxcm-1: 1029, 1078, 1369, 1377, 1732, 1741, 2876, 2913, 2942, 3611(Ref. 0228)
Me ester-3,7,23-triacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.67(s), 19-Me 0.92(s), 21-Me 0.97(d), 3a-, 7a- and 23-OCOMe 2.03, 2.07 and 2.15(each s), 4a-H 2.31(t, J, 12.5), COOMe 3.74(s), 7b-H 4.93(m), 3b-H 5.02(m), 23-H 5.07(dd, J, 11.0 1.5)(Ref. 0228)
Me ester-3,7,23-triacetate 13C-NMR (CDCl3; 125MHz) d: C-1 29.2, C-2 26.2, C-3 70.9, C-4 40.5, C-5 74.3, C-6 40.8, C-7 70.9, C-8 36.9, C-9 37.1, C-10 39.7, C-11 20.7, C-12 39.0, C-13 42.5, C-14 50.1, C-15 23.4, C-16 27.9, C-17 55.9, C-18 11.5, C-19 15.7, C-20 32.4, C-21 18.0, C-22 37.1, C-23 70.1, C-24 171.6, C-25 52.2(Ref. 0228)
Me ester-3,7,23-triacetate m/z: 486(7%), 444(72%), 426(84%), 411(18%), 390(100%), 389(28%), 385(14%), 384(16%), 366(19%), 329(71%), 325(18%), 313(20%), 311(21%), 271(40%), 269(30%), 253(29%), 226(33%), 211(33%)(Ref. 0228)







[0228]
655
(23R)-3a,7a,17a,23-Tetrahydroxy-5b-cholan-24-oic Acid
 BBA0705
Takashi Iida
C24H40O6 424.571 Download ChemDraw structure file

Me ester-3,7,23-triacetate: nmaxcm-1: 1028, 1070, 1366, 1379, 1606,1729, 2874, 2930, 3603(Ref. 0228)
Me ester-3,7,23-triacetate 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.75(s), 19-Me 0.95(s), 21-Me 0.95(d), 3a-, 7a- and 23-OCOMe 2.03, 2.06 and 2.16(each s), COOMe 3.74(s), 3b-H 4.60(m), 7b-H 4.91(m), 23-H 5.02(dd, J, 11.5, 2.5)(Ref. 0228)
Me ester-3,7,23-triacetate 13C-NMR (CDCl3; 125MHz) d: C-1 34.8, C-2 26.6, C-3 74.0, C-4 34.4, C-5 40.8, C-6 31.2, C-7 71.0, C-8 38.1, C-9 33.8, C-10 34.6, C-11 20.3, C-12 32.0, C-13 47.7, C-14 45.0, C-15 22.8, C-16 37.6, C-17 85.8, C-18 14.0, C-19 22.6, C-20 35.9, C-21 13.3, C-22 33.9, C-23 70.5, C-24 171.4, C-25 52.2(Ref. 0228)
Me ester-3,7,23-triacetate m/z: 504(9%), 486(6%), 471(7%), 444(27%), 429(7%), 426(10%), 411(18%), 384(3%), 373(5%), 366(6%), 360(10%), 351(6%), 313(32%), 288(39%), 281(8%), 271(8%), 253(61%), 228(100%), 215(37%), 213(22%), 169(40%)(Ref. 0228)







[0228]
656
3a,6a-Dihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0706
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

255-256degC, (Me ester-3,6-diacetate; mp, 182-183degC)(Ref. 0217)
[a]d-23: +62.4deg (dioxane)(Ref. 0217)
nmaxmm: 2.90, 3.05, 5.76, 5.88(Ref. 0217)









[0217]
657
3a,6b-Dihydroxy-12-oxo-5b-cholan-24-oic Acid
 BBA0707
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

279-280degC(Ref. 0216)
[a]d-25: +88deg (C=0.395, MeOH)(Ref. 0216)









[0216]
658
3,6,12-Trioxo-5b-cholan-24-oic Acid
 BBA0708
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

217-219degC, (Me ester; mp, 216-218degC)(Ref. 0216)
221-223degC, (Me ester; mp, 182-183degC)(Ref. 0217)
[a]d-26: 0deg (C=0.423, MeOH)(Ref. 0216)
[a]D: 0deg (C=0.242, MeOH) (Me ester)(Ref. 0216)
[a]31D: -21.1deg (dioxane)(Ref. 0217)









[0216] / [0217]
659
3,6,12-Trioxo-5a-cholan-24-oic Acid
 BBA0709
Takashi Iida
C24H34O5 402.524 Download ChemDraw structure file

248-249degC, (Me ester; mp, 212-214degC)(Ref. 0216/0237)
239-241degC, (Me ester; mp, 221-222degC)(Ref. 0217)
[a]d-25: +60deg (C=0.402, MeOH)(Ref. 0216/0237)
[a]D: +25deg (C=0.486, MeOH) (Me ester)(Ref. 0216/0237)
[a]31D: +32.1deg (dioxane)(Ref. 0217)









[0216] / [0217] / [0237]
660
3a-Hydroxy-7-oxo-5a-cholan-24-oic Acid
 BBA0710
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

160-161degC (Me ester)(Ref. 0237)

Me ester (70eV) m/z: 404(M+, 45%), 386(M-H2O, 11%), 372(M-32, 17%), 371(M-H2O-CH3, 6%), 368(M-2H2O, 6%), 355(M-H2O-31, 15%), 353(M-2H2O-CH3, 6%), 331(M-73, 22%), 314(M-H2O-72, 2%), 313(M-H2O-73, 3%), 292(14%), 289(M-SC, 10%), 271(M-H2O-SC, 29%), 262(M-SC-part of ring D (27), 6%), 253(M-2H2O-SC, 7%), 249(M-SC-40, 20%), 244(M-H2O-SC-27, 2%), 231(M-H2O-SC-40, 4%), 230(M-H2O-SC-41, 4%), 229(M-H2O-SC-42, 7%), 217(3%), 215(5%), 194(100%)(Ref. 0009)


Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)




[0009] / [0191] / [0237]
661
7-Oxo-5a-cholan-24-oic Acid
 BBA0711
Takashi Iida
C24H38O3 374.557 Download ChemDraw structure file

82.4degC (Me ester)(Ref. 0237)
[a]D: -41.6deg (Me ester)(Ref. 0237)
Me ester 1H-NMR(CDCl3; 90MHz) d: 18-Me 0.65(s), 21-Me 0.92(d), 19-Me 1.04(s)(Ref. 0008)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 38.2, C-2 21.7, C-3 26.4, C-4 29.0, C-5 49.1, C-6 46.5, C-7 212.1, C-8 50.1, C-9 54.7, C-10 36.6, C-11 21.1, C-12 38.7, C-13 42.5, C-14 48.9, C-15 24.9, C-16 28.2, C-17 56.1, C-18 12.0, C-19 11.6, C-20 35.2, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.5, C-25 51.3(Ref. 0065)
Me ester (70eV) m/z: 388(M+, 48%), 373(M-CH3, 2%), 370(M-H2O, 9%), 357(M-31, 6%), 356(M-32, 21%), 355(M-H2O-CH3, 15%), 317(M-71, 1%), 315(M-73, 21%), 292(15%), 273(M-SC, 12%), 271(M-117, 2%), 262(1%), 255(M-H2O-SC, 39%), 246(M-SC-part of ring D, 13%), 233(M-SC-40, 20%), 231(M-SC-ring D, 35%), 178(100%)(Ref. 0009)







[0008] / [0009] / [0065] / [0237]
662
6b,12a-Dihydroxy-5b-cholan-24-oic Acid
 BBA0712
Takashi Iida
C24H40O4 392.572 Download ChemDraw structure file


Me ester (70eV) m/z: 406(M+, 1%), 388(M-H2O, 3%), 373(M-H2O-CH3, 15%), 370(M-2H2O, 17%), 357(M-H2O-31, 15%), 355(M-2H2O-CH3, 1%), 273(M-H2O-SC, 14%), 264(M-SC-part of ringD (27), 1%), 255(M-2H2O-SC, 100%), 249(M-SC-ring D (42), 3%), 246(M-H2O-SC-27, 1%), 228(M-2H2O-SC-27, 4%), 213(M-2H2O-SC-42, 6%)(Ref. 0009)







[0009]
663
3-Oxochola-1,4,6-trien-24-oic Acid
 BBA0713
Takashi Iida
C24H32O3 368.509 Download ChemDraw structure file

Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 152.7, C-2 128.0, C-3 186.1, C-4 123.6, C-5 162.5, C-6 127.4, C-7 138.4, C-8 38.1, C-9 48.2, C-10 41.1, C-11 20.6, C-12 39.3, C-13 42.9, C-14 53.5, C-15 23.5, C-16 27.9, C-17 55.5, C-18 11.9, C-19 21.7, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.3, C-25 51.4(Ref. 0251)








[0251]
664
6b-Hydroxy-3-oxochol-4-en-24-oic Acid
 BBA0714
Takashi Iida
C24H36O4 388.540 Download ChemDraw structure file

Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 37.0, C-2 34.1, C-3 200.3, C-4 126.0, C-5 168.6, C-6 72.9, C-7 38.5, C-8 29.6, C-9 53.5, C-10 37.9, C-11 20.9, C-12 39.5, C-13 42.4, C-14 55.7, C-15 24.0, C-16 27.9, C-17 55.7, C-18 11.9, C-19 19.3, C-20 35.2, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0251)








[0251]
665
6b,12a-Dihydroxy-3-oxochol-4-en-24-oic Acid
 BBA0715
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

184-186degC (Me ester)(Ref. 0030)
Me ester: nmaxmcm-1: 1691, 1734(C=O), 980, 1039, 3500(OH)(Ref. 0030)
Me ester 1H-NMR(CDCl3; 90MHz) d: 18-Me 0.77(s), 21-Me 0.98(d), 19-Me 1.36(s), COOMe 3.66(s), 12b-H 4.06(m), 6a-H 4.34(m), 4-H 5.80(brs)(Ref. 0030)
Me ester 13C-NMR(CDCl3; 125.65MHz) d: C-1 36.8, C-2 34.0, C-3 200.3, C-4 126.0, C-5 168.6, C-6 72.4, C-7 38.2, C-8 29.8, C-9 46.9, C-10 37.4, C-11 28.6, C-12 72.8, C-13 46.3, C-14 46.9, C-15 23.4, C-16 27.2, C-17 46.9, C-18 12.6, C-19 19.2, C-20 35.0, C-21 17.2, C-22 30.8, C-23 31.0, C-24 174.5, C-25 51.4(Ref. 0251)








[0030] / [0251]
666
12a-Hydroxy-3,6-dioxo-5b-cholan-24-oic Acid
 BBA0716
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

186-188degC (Me ester-12-formate)(Ref. 0030)
Me ester-12-formate: nmaxmcm-1: 1182(formate), 1706(C=O)(Ref. 0030)
Me ester-12-formate 1H-NMR(CDCl3; 90MHz) d: 18-Me 0.80(s), 21-Me 0.85(d), 19-Me 0.96(s), COOMe 3.66(s), 12b-H 5.35(m), 12a-CHO 8.16(s)(Ref. 0030)








[0030]
667
3b-Hydroxychola-5,7-dien-24-oic Acid
 BBA0717
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

114-115degC (Me ester)(Ref. 0241)
Me ester: lmax (EtOH): 282 nm(Ref. 0241)
Me ester: nmaxcm-1: 1610, 1660(-CH=CH-CH=CH-), 1720(CO), 3500(OH)(Ref. 0241)
Me ester 1H-NMR (CDCl3; 60MHz) d: 18-Me 0.71(s), 19-Me 0.96(s), COOMe 3.65(s), Olefinic 2H 5.5-5.9(dd, J, 6.0)(Ref. 0241)








[0241]
668
4,12a-Dihydroxy-3-oxochol-4-en-24-oic Acid
 BBA0718
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

Me ester-4,12-diacetate: nmaxcm-1: 1630(C=C), 1687(C=C-C=O), 1735(12a-OCOMe and COOMe), 1760(4a-OCOMe)(Ref. 0232)
Me ester-4,12-diacetate 1H-NMR (CDCl3) d: 18-Me 0.79(s), 19-Me 1.22(s), 12a-OCOMe 2.02(s), 4-OCOMe 2.21(s), COOMe 3.67(s), 12b-H 5.09(Ref. 0232)
Me ester-4,12-diacetate m/z: 502(M, 0%), 460(M-C2H2O, 21%), 400(M-C2H2O-AcOH, 22%), 385(M-C2H2O-AcOH-CH3, 15%), 261(C17H25O2, 100%)(Ref. 0232)







[0232]
669
2,12a-Dihydroxy-3-oxo-5b-chol-1-en-24-oic Acid
 BBA0719
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

165-167degC (Me ester-2,12-diacetate)(Ref. 0232)
Me ester-2,12-diacetate: nmaxcm-1: 1645(C=C), 1692(C=C-C=O), 1735(12a-OCOMe and COOMe), 1760(2-OCOMe)(Ref. 0232)
Me ester-2,12-diacetate 1H-NMR (CDCl3) d: 18-Me 0.78(s), 19-Me 1.21(s), 12a-OCOMe 2.02(s), 2-OCOMe 2.18(s), COOMe 3.68(s), 12b-H 5.07, 1-H 6.31(s)(Ref. 0232)
Me ester-2,12-diacetate m/z: 502(M, 2%), 460(M-C2H2O, 6%), 442(M-AcOH, 4%), 400(M-C2H2O-AcOH, 14%), 285(M-C2H2O-AcOH-C6H11O2, 32%), 137(100%)(Ref. 0232)







[0232]
670
3b-Hydroxychola-5,16-dien-24-oic Acid
 BBA0720
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

121-123degC (Me ester-3-acetate)(Ref. 0223)
[a]D: +62.4deg (Me ester-3-acetate)(Ref. 0223)
Me ester-3-acetate 1H-NMR(CDCl3) d: 18-Me 0.78(s), 21-Me 1.01(d), 19-Me 1.05(s), 3b-OCOMe 2.03(s), COOMe 3.66(s), 16-H 5.32(brm), 6-H 5.36(brm)(Ref. 0223)








[0223]
671
(20S)-3b-Hydroxychola-5,16-dien-24-oic Acid
 BBA0721
Takashi Iida
C24H36O3 372.541 Download ChemDraw structure file

112.5-113.5degC (Me ester-3-acetate)(Ref. 0223)
[a]D: -55.9deg (Me ester-3-acetate)(Ref. 0223)
Me ester-3-acetate 1H-NMR(CDCl3) d: 18-Me 0.80(s), 19-Me 1.05(s), 21-Me 1.07(d), 3b-OCOMe 2.02(s), COOMe 3.65(s), 16-H 5.34(brm), 6-H 5.35(brm)(Ref. 0223)








[0223]
672
3a,7a-Dihydroxy-5b-chol-16-en-24-oic Acid
 BBA0722
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

109-110degC (Me ester-3,7-diacetate)(Ref. 0262)
[a]D: +1.36deg (C=1.03, CHCl3) (Me ester-3,7-diacetate)(Ref. 0262)
Me ester-3,7-diacetate: nmaxcm-1: 1735(Ref. 0262)
Me ester-3,7-diacetate 1H-NMR (CDCl3; 100MHz) d: 0.71(s), 0.95(s), 1.01(d), 2.00(s), 2.02(s), 3.64(s), 4.60(m), 4.95(brs), 5.28(brs)(Ref. 0262)








[0262]
673
3a,7a-Dihydroxy-22-oxo-5b-cholan-24-oic Acid
 BBA0723
Takashi Iida
C24H38O5 406.556 Download ChemDraw structure file

49-51degC (Et ester-3,12-diacetate)(Ref. 0264)
Et ester-3,7-diacetate: nmaxcm-1: 1620, 1640, 1740(C=O)(Ref. 0264)
Et ester-3,7-diacetate 1H-NMR (CDCl3) d: 18-Me 0.72(s), 19-Me 0.98(s), CH2CH3 1.27(t, J, 6.0), 7a-OCOMe 1.95(s), 3a-OCOMe 2.00(s), 23-H2 2.13-3.38(s), CH2CH3 4.11(q, J, 6.0), 3b- and 7b-H 4.33-4.93(brm), 22-enolic OH 11.87(s)(Ref. 0264)








[0264]
674
6a-Hydroxy-3,7-dioxo-5b-cholan-24-oic Acid
 BBA0724
Takashi Iida
C24H36O5 404.540 Download ChemDraw structure file

Me ester: nmaxcm-1: 1711, 1741 (C=O)(Ref. 0259)
Me ester 1H-NMR (CDCl3; 270MHz) d: 18-Me 0.71(s), 21-Me 0.94(d), 19-Me 1.35(s), COOMe 3.67(s), 12b-H 4.55(m)(Ref. 0259)
Me ester (70eV) m/z: 418(M+, 25%), 400(M+-H2O, 12%), 386(M+-32, 24%), 345(M+-73, 12%), 00(M+-H2O, 10%), 303(M+-SC, 14%), 285(M+-H2O-SC, 18%), 134(100%)(Ref. 0259)







[0259]
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TITLE:Stero-Bile Acids And Bile Sterols. Lxiv. The Isolation And The Chemistry Of A New Bile Alcohol, 3-Alpha, 7-Alpha, 12-Alpha, 24-Xi, 26-Pentahydroxybishomocholane From Rana Catesbiana Bile PubMed ID:14271905
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TITLE:Identification of 5b-cholestane-3a,7a,12a,23b-tetrol, 5b-cholestane-3a,7a,12a,24a-tetrol, and 5b-cholestane-3a,7a,12a,24
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