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Bile acid


DATA No : BBA0133 INFORMANT : Takashi Iida

NAME : 12-Oxo-5a-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:184-186degC(Ref. 0001)
112.5-114.0degC (Me ester)(Ref. 0014)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20: +108deg (C=2, CHCl3)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmaxcm-1: 1703, 1743 (C=O)(Ref. 0014)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.86(d), 18-Me 0.89(s), 19-Me 1.02(s), COOMe 3.65(s)(Ref. 0008/0014)
13C-NMR (CDCl3; 22.53MHz) d: C-1 38.3, C-2 21.9, C-3 26.5, C-4 28.8, C-5 46.9, C-6 28.8, C-7 31.5, C-8 35.7, C-9 57.8, C-10 37.7, C-11 38.3, C-12 215.2, C-13 57.2, C-14 58.6, C-15 24.3, C-16 27.4, C-17 46.4, C-18 11.7, C-19 11.9, C-20 35.3, C-21 18.6, C-22 31.3, C-23 30.6, C-24 174.6, C-25 51.4(Ref. 0065)

MASS SPECTRA:Me ester (70eV) m/z: 388(M+, 69%), 373(M-CH3, 1%), 370(M-H2O, 6%), 357(M-31, 3%), 356(M-32, 1%), 355(M-H2O-CH3, 2%), 333(M-55, 3%), 315(M-73, 1%), 273(M-SC, 15%), 271(M-117, 4%), 255(M-H2O-SC, 9%), 246(M-SC-part of ring D (27), 4%), 233(M-SC-40, 100%), 231(M-SC-ring D (42), 5%)(Ref. 0009)

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]

[0014]
AUTHOR:Iida, T., Tamura, T., Matsumoto, T., and Chang, F. C.
TITLE:Potential bile acid metabolites. 9. 3,12-Dihydroxy- and 12 beta-hydroxy-5 alpha-cholanoic acids PubMed ID:4031665
JOURNAL:J Lipid Res.
VOL:26 PAGE : 874-881 (1985)
[TOP]

[0065]
AUTHOR:Momose, T., Iida, T., Tamura, T., and Matsumoto, T.
TITLE:13C-NMR Spectra of Oxo-bile Acid Methyl Esters.
JOURNAL:J. Jpn. Oil Chem. Soc. (Yukagaku)
VOL:36 PAGE : 954 -957 (1987)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.