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Bile acid


DATA No : BBA0040 INFORMANT : Takashi Iida

NAME : 3a,12a-Dihydroxy-5b-cholan-24-oic Acid

COMMON NAME: Deoxycholic Acid
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:173.8-174.4degC, (Me ester; mp, 75.5-95.5degC)(Ref. 0025)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +49.8deg (dioxane), +54.1deg (EtOH)(Ref. 0025)
[a]20.5D: +48deg (butanore) (Me ester)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:lmax mm: 5.80(COOH), 2.95, 9.65 (OH)(Ref. 0003/0025)
Me ester nmax m: 9.65, 9.87, 10.32, 10.56(Ref. 0003)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.91(s), 21-Me 0.96(d), 3b-H 3.5(brm),12b-H 3.93(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.1, C-2 30.2, C-3 71.4, C-4 36.2, C-5 42.0, C-6 27.1, C-7 26.0, C-8 35.9, C-9 33.3, C-10 33.9, C-11 28.5, C-12 72.8, C-13 46.3, C-14 47.9, C-15 23.6, C-16 27.4, C-17 47.0, C-18 12.5, C-19 22.9, C-20 35.1, C-21 17.1, C-22 31.0, C-23 30.8, C-24 174.5, C-25 51.2(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 4%), 370(M-2H2O, 21%), 273(M-H2O-SC, 72%), 255(M-2H2O-SC, 100%), 213(M-2H2O-SC-ring D (42), 13%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Common bile acid in many vertebrate.(Ref. 0100)
Occurred in bile of human, ox, rabbit, goat, sheep, and rat.(Ref. 0101)
Bacterial 7-dehydroxylation product of cholic acid.(Ref. 0102)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
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]

[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]

[0006]
AUTHOR:Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C.
TITLE:Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers.
JOURNAL:Org. Magn. Reson.
VOL:21 PAGE : 305 -309 (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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[0010]
AUTHOR:Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T.
TITLE:High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids.
JOURNAL:Biomed. Mass Spectrom.
VOL:9 PAGE : 473 -476 (1982)
[TOP]

[0025]
AUTHOR:Chang, F. C., Wood, N. F., and Holton, W. G.
TITLE:3 Beta, 12 Beta-Dihydroxycholanic Acid PubMed ID:14325490
JOURNAL:J Org Chem.
VOL:30 PAGE : 1718-1723 (1965)
[TOP]

[0100]
AUTHOR:Haselwood, G. A. D. (1978) The Biological Importance of Bile Salts, in Frontiers of Biology (Vol. 47) (Neuberger, A., and Tatum, E. L. eds), North-Holland Publishing Co., Amsterdam.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[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:
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[0102]
AUTHOR:Hofmann, A. F., Schteingart, C. D., and Hagey, L. R. (1995) Species Differences in Bile Acid Metabolism, in Bile Acids in Liver Diseases (Paumgartner, G., and Beuers, U. eds), pp 3-30, Kluwer Academic Publishers, Dordrecht.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0150]
AUTHOR:Alme, B., Bremmelgaard, A., Sjovall, J., and Thomassen, P.
TITLE:Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry PubMed ID:864325
JOURNAL:J Lipid Res.
VOL:18 PAGE : 339-362 (1977)
[TOP]

[0151]
AUTHOR:Bremmelgaard, A., and Sjovall, J.
TITLE:Bile acid profiles in urine of patients with liver diseases PubMed ID:118027
JOURNAL:Eur J Clin Invest.
VOL:9 PAGE : 341-348 (1979)
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