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Bile acid


DATA No : BBA0131 INFORMANT : Takashi Iida

NAME : 7-Oxo-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H38O3 MOL.WT (average) : 374.557


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:150-151degC, (Me ester; mp, 92-93degC)(Ref. 0001)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1700-1730(Ref. 0063)

NMR SPECTRA:1H-NMR (CDCl3) d: 18-Me 0.67 (s), 19-Me 1.19 (s)(Ref. 0063)
Me ester 1H-NMR (CDCl3) d: 18-Me 0.66 (s), 19-Me 1.18 (s), COOMe 3.65(s)(Ref. 0005/0063)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.4, C-2 21.6, C-3 26.5, C-4 28.1, C-5 47.6, C-6 45.8, C-7 212.2, C-8 49.5, C-9 42.8, C-10 35.8, C-11 20.6, C-12 39.0, C-13 42.8, C-14 49.0, C-15 24.8, C-16 28.1, C-17 54.8, C-18 12.0, C-19 23.8, C-20 35.2, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.4, C-25 51.3(Ref. 0004/0064)

MASS SPECTRA:Me ester (22eV) m/z: 388(M+, 50%), 370(M-H2O, 21%), 356(M-CH3OH, 50%), 355(M-CH3-H2O, 16%), 341(M-CH3OH-CH3, 10%), 339(M-CH3O-H2O, 16%), 323(M-CH3OH-H2O-CH3, 12%), 315(M-part of SC, 97%), 297(315-H2O, 10%), 292(M-ring A, 100%), 273(M-SC, 35%), 170(M-SC-ring A, 30%), 255(M-H2O-SC, 75%), 115(SC fragment, 12%), 74(SC fragment, 20%)(Ref. 0009/0039)

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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[0004]
AUTHOR:Barnes, S., and Kirk, D. N. (1988) Nuclear Magnetic Resonance Spectroscopy of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchell, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp65-136, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0005]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:24 PAGE : 163 -165 (1983)
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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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[0039]
AUTHOR:Lee, S. P., Lester, R., and Pyrek, J. S.
TITLE:Vulpecholic acid (1 alpha, 3 alpha, 7 alpha-trihydroxy-5 beta-cholan-24-oic acid): a novel bile acid of a marsupial, Trichosurus vulpecula (Lesson) PubMed ID:3559398
JOURNAL:J Lipid Res.
VOL:28 PAGE : 19-31 (1987)
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[0063]
AUTHOR:Sawaya, T., and Kimura, M.
TITLE:Autoxidation of Cholanic Acid in the Presence of Ferrous Ions.
JOURNAL:Chem. Pharm. Bull.
VOL:31 PAGE : 1207 -1212 (1983)
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[0064]
AUTHOR:Iida, T., Tamura, T., Matsumoto, T., and Chang, F. C.
TITLE:Carbon-13 NMR Spectra of Oxobile Acid Methyl Esters.
JOURNAL:J. Jpn. Oil Chem. Soc. (Yukagaku)
VOL:32 PAGE : 232 -233 (1983)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.