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Bile acid


DATA No : BBA0095 INFORMANT : Takashi Iida

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

COMMON NAME:
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:242-243degC, (Me ester; mp, 110-111degC)(Ref. 0033)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1675(C=O), 3200, 1010(OH)(Ref. 0033)

NMR SPECTRA: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)

MASS SPECTRA: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)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

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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[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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[0033]
AUTHOR:Iida, T., Shinohara, T., Momose, T., Tamura, T., Matsumoto, T., Nambara, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites;12. Synthesis of Stereoisomeric 3,7,12-Trihydroxy-5a-cholanic Acids and Related Compounds.
JOURNAL:Synthesis
VOL: PAGE : 998 -1004 (1986)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.