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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)




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)




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)




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)




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)




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)




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)







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)









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)







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)








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)







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)




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)







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)







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)







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)







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)







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)







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)








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)




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)




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)




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)







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)




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)




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)




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)







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)








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)








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)








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)








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)



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)




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)




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)




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)




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)







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)




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)




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)




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)




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)




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)




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)




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)




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)




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)







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)




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)







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)







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)







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)







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)







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)







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)







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)







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)




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)




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)







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)




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)




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)




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)




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)




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)




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)




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)




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)







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)







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)







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)







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)







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)




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)







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)







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)







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)







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)







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)







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)




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)




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)







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)







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)




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)




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)




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)







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)




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)







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)




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)







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)




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)







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)







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)







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)




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)







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)




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)







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)







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)




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)




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)




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)









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)









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)







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)




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)




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)




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)







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)




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)




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)




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)




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)




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)




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)




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)




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)







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)




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)




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)







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)







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)







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)







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)




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)




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)




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)







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)








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)







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)







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)







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)







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)







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)







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)







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)




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)







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)







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)







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)









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)









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)







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)







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)







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)








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)




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)








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)




151
3b-Hydroxy-7-oxo-5b-cholan-24-oic Acid
BBA0151
Takashi Iida
C24H38O4 390.556 Download ChemDraw structure file

247-248degC (Ref. 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)







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)









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)









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)




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)




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)








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)




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)








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)









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)




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)








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)







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)








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)








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)








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)








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)




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)







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)







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)









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)









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)








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)







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)








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)




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)








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)








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)








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)








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)








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)








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)








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)




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)








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)









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)









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)









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)







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)




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)







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)




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)




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)




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)




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)




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)







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)









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)









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)







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)



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)







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)








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)







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)








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)









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)








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)








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)









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)




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)








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)







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)







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)









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)




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)




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)




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)




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)




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)







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)







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)







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)