Back to HOME

Bile acid


DATA No : BBA0115 INFORMANT : Takashi Iida

NAME : 2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O6 MOL.WT (average) : 424.571


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:230-232degC, (Me ester; mp, 197-199degC)(Ref. 0015)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-18: +27.2pm2deg (C=1.03, EtOH)(Ref. 0218)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1702(C=O), 3436, 978(OH)(Ref. 0015)

NMR SPECTRA: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)

MASS SPECTRA:(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)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0007]
AUTHOR:Lawson, A. M., and Setchell, K. D. R. (1988) Mass Spectrometry of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchall, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp 167-267, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0015]
AUTHOR:Iida, T., Komatsubara, I., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. 17. Synthesis of 2 beta-hydroxylated bile acids PubMed ID:2042229
JOURNAL:Steroids.
VOL:56 PAGE : 114-122 (1991)
[TOP]

[0155]
AUTHOR:Clayton, P. T., Muller, D. P. R., and Lawson, A. M.
TITLE:The Bile Acids Composition of Gastric Contents from Neonates with High Intestinal Obstruction. PubMed ID:7150258
JOURNAL:Biochem. J.
VOL:206 PAGE : 489 -498 (1982)
[TOP]

[0188]
AUTHOR:Meng, L. J., Reyes, H., Palma, J., Hernandez, I., Ribalta, J., and Sjovall, J.
TITLE:Effects of ursodeoxycholic acid on conjugated bile acids and progesterone metabolites in serum and urine of patients with intrahepatic cholestasis of pregnancy PubMed ID:9453429
JOURNAL:J Hepatol.
VOL:27 PAGE : 1029-1040 (1997)
[TOP]

[0218]
AUTHOR:Haslewood, G. A. D., and Tökes, L.
TITLE:Comparative Studies of Bile Salts. A New Type of Bile Salt from Arapaima gigas (Cuvier). (Family Osteoglossidae). PubMed ID:5073728
JOURNAL:Biochem. J.
VOL:126 PAGE : 1161 -1170 (1972)
[TOP]

[0245]
AUTHOR:Ikegawa, S., Yoshimura, T., Ito, K., Kurosawa, T., and Thoma, M.
TITLE:Simultaneous Fluorometric Determination of Conjugated Fetal Bile Acids in Urine of Newborns by High-Perfomance Liquid Chromatoguraphy.
JOURNAL:Anal. Sci.
VOL:11 PAGE : 91 -96 (1995)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.