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Bile acid


DATA No : BBA0141 INFORMANT : Takashi Iida

NAME : 7,12-Dioxo-5a-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H36O4 MOL.WT (average) : 388.540


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:194degC, (Me ester; mp, 143-144degC)(Ref. 0038/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +11.0pm1deg (C=0.94)(Ref. 0038/0237)
[a]d-25: +9.4deg (C=0.99, MeOH) (Me ester)(Ref. 0001/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 3226, 1736, 1706, 1698, 897, 789(Ref. 0038)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.84(d), 18-Me 1.04(s), 19-Me 1.15(s)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.3, C-3 26.0, C-4 28.7, C-5 48.3, C-6 46.2, C-7 209.2, C-8 49.3, C-9 58.0, C-10 37.1, C-11 37.9, C-12 212.7, C-13 56.4, C-14 51.6, C-15 25.1, C-16 27.4, C-17 45.3, C-18 11.5, C-19 11.1, C-20 35.3, C-21 18.4, C-22 31.0, C-23 30.3, C-24 174.1, C-25 51.1(Ref. 0065)

MASS SPECTRA:Me ester (70eV) m/z: 402(M+, 41%), 387(M-CH3, 4%), 384(M-H2O, 27%), 370(M-32, 5%), 366(M-2H2O, 3%), 353(M-H2O-31, 7%), 329(M-73, 11%), 287(M-SC, 28%), 269(M-H2O-SC, 17%), 261(M-SC-26, 5%), 260(M-SC-part of ring D (27), 10%), 251(M-2H2O-SC, 3%), 247(M-SC-40, 100%), 246(M-SC-41, 4%), 245(M-SC-ring D (42), 3%)(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]

[0038]
AUTHOR:Mitra, M. N., and Elliott, W. H.
TITLE:Bile acids. 23. A new direct synthesis of allocholic acid and its 3 beta isomer PubMed ID:5634890
JOURNAL:J Org Chem.
VOL:33 PAGE : 175-181 (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)
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[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 : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.