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Bile acid


DATA No : BBA0038 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:271-272degC, (Me ester; mp, 106-161degC)(Ref. 0023)159-160degC (Me ester)(Ref. 0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +14deg (Me ester)(Ref. 0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA: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)

NMR SPECTRA: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)

MASS SPECTRA: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)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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)
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[0009]
AUTHOR:Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[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)
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[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)
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[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)
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[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)
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[0237]
AUTHOR:Elliott, W. H. (1971) Allo Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1: Chemistry) (Nair, P. P., and Kritchevsky, D. eds), pp47-93, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.