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Bile acid


DATA No : BBA0106 INFORMANT : Takashi Iida

NAME : 3,7,12-Trioxo-5b-cholan-24-oic Acid

COMMON NAME: Dehydrocholic Acid
SYMBOL:
FORMULA: C24H34O5 MOL.WT (average) : 402.524


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:237degC(Ref. 0001)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20: +26deg(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax m: 9.6-9.7, 9.91(Ref. 0003)
Me ester: nmax m: 9.68, 9.91(Ref. 0003)

NMR SPECTRA:Me ester 1H-NMR (CDCl3) d: 1.07 (3H, s, 18-CH3), 1.39 (3H, s, 19-CH3), 0.84 (3H, d, J=5Hz, 21-CH3), 3.63 (3H, s, COOCH3)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.2, C-2 36.4, C-3 208.6, C-4 42.7, C-5 46.7, C-6 44.9, C-7 208.4, C-8 49.0, C-9 45.7, C-10 36.0, C-11 38.6, C-12 211.6, C-13 56.9, C-14 51.8, C-15 25.1, C-16 27.5, C-17 45.6, C-18 11.7, C-19 21.8, C-20 35.4, C-21 18.5, C-22 31.3, C-23 30.4, C-24 174.3, C-25 51.3(Ref. 0004/0064)

MASS SPECTRA:Me ester (70eV) m/z: 416(M+, 90%), 398(M-H2O, 100%), 384(M-32, 9%), 380(M-2H2O, 3%), 367(M-H2O-31, 2%), 343(M-73, 18%), 301(M-SC, 30%), 283(M-H2O-SC, 33%), 275(M-SC-26, 7%), 274(M-SC-part of ring D (27), 18%), 265(M-2H2O-SC, 5%), 261(M-SC-40, 96%), 260(M-SC-41, 2%), 259(M-SC-ring D (42), 5%)(Ref. 0009)
The spectrum (70eV) was shown as the Me-ester derivative(Ref. 0007)

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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[0003]
AUTHOR:Levin, S. J., and Johnston, C. G.
TITLE:Infrared Correlations in the Bile Acid Series
JOURNAL:Talanta.
VOL:8 PAGE : 871 -879 (1961)
[TOP]

[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)
[TOP]

[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:
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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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[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.