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Bile acid


DATA No : BBA0097 INFORMANT : Takashi Iida

NAME : 3a,7b,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:243-244degC, (Me ester; mp, 178-179degC)(Ref. 0033)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +50deg (EtOH)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1735, 1710(C=O), 3280, 1028, 1005(OH)(Ref. 0033)

NMR SPECTRA:1H-NMR (CDCl3+50%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.75(s), 21-Me 0.97(d), 7a- and 12a-H 3.27(brm), 3b-H 3.86(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.74(s), 19-Me 0.79(s), 21-Me 0.99(d), 7a- and 12a-H 3.33(brm), COOMe 3.65(s), 3b-H 3.97(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 31.5, C-2 28.1, C-3 64.4, C-4 34.8, C-5 35.5, C-6 38.0, C-7 73.4, C-8 41.2, C-9 50.5, C-10 34.5, C-11 28.6, C-12 78.4, C-13 47.6, C-14 53.3, C-15 25.6, C-16 23.0, C-17 55.8, C-18 7.4, C-19 10.5, C-20 31.7, C-21 20.4, C-22 31.5, C-23 30.3, C-24 173.6, C-25 50.4 (Ref. 0011)

MASS SPECTRA:Me ester (20eV) m/z: 404(M-H2O, 6%), 386(M-2H2O, 26%), 289(M-H2O-SC, 100%), 271(M-2H2O-SC, 52%), 253(M-3H2O-SC, 16%)(Ref. 0012/0033)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Hill, R. A., Kirk, D. N., Makin, H. L. J., and Murphy, G. M. (1991) Chemical Data, Structures and Bibliographies, in Dictionary of Steroids, Chapman & Hall, London.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[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)
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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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