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Bile acid


DATA No : BBA0093 INFORMANT : Takashi Iida

NAME : 3a,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:210.5-212degC, (Me ester; mp, 126-127.5degC)(Ref. 0033)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1700(C=O), 3450, 1010, 995(OH)(Ref. 0033)

NMR SPECTRA: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)

MASS SPECTRA: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)

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.