Back to HOME

Bile acid


DATA No : BBA0039 INFORMANT : Takashi Iida

NAME : 3b,7b-Dihydroxy-5a-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:245-246.5degC, (Me ester; mp, 159-160degC)(Ref. 0023)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1690(C=O), 3400, 1034(OH)(Ref. 0023)
Me ester: nmax cm-1: 1735 (C=O), 3340, 1037 (OH)(Ref. 0023)

NMR SPECTRA: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)

MASS SPECTRA: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)

OTHER SPECTRA:
CHROMATOGRAM DATA

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

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0008]
AUTHOR:Iida, T., and Shinohara, T.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part2. Mono-, Di- and Trisubstituted Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:28 PAGE : 175 -179 (1987)
[TOP]

[0011]
AUTHOR:Iida, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Carbon-13 Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part II. Mono-, Di- and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:Chem. Phys. Lipids
VOL:45 PAGE : 1 -12 (1987)
[TOP]

[0012]
AUTHOR:Iida, T., Tamura, T., and Matsumoto, T.
TITLE:Mass Spectra of Mono-, Di-, and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:29 PAGE : 279 -288 (1988)
[TOP]

[0023]
AUTHOR:Iida, T., Momose, T., Nambara, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. X. Syntheses of Stereoisomeric 3,7-Dihydroxy-5a-cholanic Acids.
JOURNAL:Chem. Pharm. Bull.
VOL:34 PAGE : 1929 -1933 (1986)
[TOP]

[0187]
AUTHOR:Marschall, H. U., Matern, H., Wietholtz, H., Egestad, B., Matern, S., and Sjovall, J.
TITLE:Bile acid N-acetylglucosaminidation. In vivo and in vitro evidence for a selective conjugation reaction of 7 beta-hydroxylated bile acids in humans PubMed ID:1602004
JOURNAL:J Clin Invest.
VOL:89 PAGE : 1981-1987 (1992)
[TOP]

[0191]
AUTHOR:Nakagawa, M., Colombo, C., and Setchell, K. D.
TITLE:Comprehensive study of the biliary bile acid composition of patients with cystic fibrosis and associated liver disease before and after UDCA administration PubMed ID:2391071
JOURNAL:Hepatology.
VOL:12 PAGE : 322-334 (1990)
[TOP]

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