Back to HOME

Bile acid


DATA No : BBA0128 INFORMANT : Takashi Iida

NAME : 3-Oxo-5a-cholan-24-oic Acid

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


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:183-184degC, (Me ester; mp, 113-114degC)(Ref. 0013/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +32.6pm0.5deg (C=0.98, MeOH)(Ref. 0013/0237)
[a]D: +40.5deg (Me ester)(Ref. 0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmaxcm-1: 1739, 1715, 1228, 985(Ref. 0013)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.92(s), 21-Me 1.01(d)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 38.5, C-2 38.0, C-3 221.6, C-4 44.6, C-5 46.6, C-6 28.9, C-7 31.6, C-8 35.3, C-9 53.7, C-10 35.5, C-11 21.3, C-12 39.8, C-13 42.6, C-14 56.2, C-15 24.1, C-16 28.0, C-17 55.9, C-18 12.0, C-19 11.4, C-20 35.3, C-21 18.2, C-22 30.9, C23 30.9, C-24 174.5, C-25 51.3(Ref. 0065)

MASS SPECTRA:Me ester (70eV) m/z: 388(M+, 39%), 373(M-CH3, 20%), 370(M-H2O, 4%), 357(M-31, 9%), 356(M-32, 14%), 355(M-H2O-CH3, 5%), 318(7%), 317(M-71, 3%), 315(M-73, 7%), 273(M-SC, 4%), 271(M-117, 4%), 262(3%), 255(M-H2O-SC, 3%), 246(M-SC-part of ring D (27), 35%), 233(M-SC-40, 16%), 231(M-SC-ring D (42), 100%), 178(3%)(Ref. 0009)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected in human faeces.(Ref. 0101/0205)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0007]
AUTHOR:Lawson, A. M., and Setchell, K. D. R. (1988) Mass Spectrometry of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchall, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp 167-267, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[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]

[0013]
AUTHOR:Mitra, M. N., and Elliott, W. H.
TITLE:Bile acids. XXIV. Raney nickel in the preparation of allocholanic acids PubMed ID:5742844
JOURNAL:J Org Chem.
VOL:33 PAGE : 2814-2818 (1968)
[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)
[TOP]

[0101]
AUTHOR:Matschiner, J. T. (1971) Naturally Occurring Bile Acids and Alcohols and their Origins. In The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1 : Chemistry) (Nair, P. P., and Krichevsky, D. eds), pp. 11-46, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0205]
AUTHOR:Tandon, R., Axelson, M., and Sjovall, J.
TITLE:Selective liquid chromatographic isolation and gas chromatographic-mass spectrometric analysis of ketonic bile acids in faeces PubMed ID:6501503
JOURNAL:J Chromatogr.
VOL:302 PAGE : 1-14 (1984)
[TOP]

[0237]
AUTHOR:Elliott, W. H. (1971) Allo Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1: Chemistry) (Nair, P. P., and Kritchevsky, D. eds), pp47-93, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.