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Bile acid


DATA No : BBA0055 INFORMANT : Takashi Iida

NAME : 7b,12a-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:207.5-208.5degC, (Me ester ; mp, 133.5-14.0degC)(Ref. 0028)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +76.7deg (C=0.45, MeOH) (Me ester)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1685(C=O), 3300, 1028, 990(OH)(Ref. 0028)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.78(s), 21-Me 0,99(d), 7a-H 3.26(brm), 12b-H 3.90(m)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.80(s), 21-Me 0.99(d), 7a-H 3.38(brm), COOMe 3.66(s), 12b-H 3.98(brm)(Ref. 0008/0028)
13C-NMR (CDCl3; 22.53MHz) d: C-1 38.5, C-2 22.0, C-3 26.5, C-4 28.5, C-5 44.0, C-6 38.7, C-7 74.9, C-8 43.6, C-9 45.7, C-10 35.2, C-11 28.6, C-12 72.4, C-13 47.3, C-14 47.6, C-15 26.3, C-16 27.7, C-17 46.0, C-18 12.7, C-19 12.1, C-20 34.9, C-21 17.3, C-22 31.0, C-23 30.9, C-24 174.4, C-25 51.3(Ref. 0011)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 3%), 370(M-2H2O, 20%), 355(M-2H2O-CH3, 6%), 273(M-H2O-SC, 78%), 255(M-2H2O-SC, 100%)(Ref. 0009/0012/0028)

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]

[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 : - ()
[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)
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[0028]
AUTHOR:Iida, T., Momose, T., Chang, F. C., and Nambara, T.
TITLE:Potential Bile Acid Metabolites. XI. Syntheses of Stereoisomeric 7,12-Dihydroxy-5a-cholanoic Acids.
JOURNAL:Chem. Pharm. Bull.
VOL:34 PAGE : 1934 -1938 (1986)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.