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Bile acid


DATA No : BBA0084 INFORMANT : Takashi Iida

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

COMMON NAME: Cholic Acid
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:197degC, (Me ester; mp, 162degC)(Ref. 0001)
176-178degC (Me ester-3,7-diacetate)(Ref. 0247)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20: +37deg (EtOH), [a]d-20: +25deg (Me ester)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:Me ester 1H-NMR(CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.87(s), 21-Me 0.97(d), 3b-H 3.5(brm), 7b-H 3.75(m), 12b-H 3.88(m)(Ref. 0004/0005)
Me ester-3,7-diacetate 1H-NMR(CDCl3) d: 18-Me 0.68(s), 19-Me 0.96(s), 21-Me 1.00(d), 3a- and 7a-OCOMe 2.05, 2.10(each s), 23-H2 2.25(m), COOMe 3.65(s), 12b-H 3.95(m), 3b-H 4.59(brm), 7b-H 4.85(m)(Ref. 0247)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 35.3, C-2 30.1, C-3 71.7 C-4 39.4, C-5 41.4, C-6 34.7, C-7 68.3, C-8 39.4, C-9 26.2, C-10 34.7, C-11 28.0, C-12 73.0, C-13 46.3, C-14 41.4, C-15 23.1, C-16 27.4, C-17 46.8, C-18 12.3, C-19 22.3, C-20 35.3, C-21 17.4, C-22 31.0, C-23 31.0, C-24 174.7, C-25 51.4(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 402(M-H2O, 2%), 386(M-2H2O, 43%), 371(M-2H2O-CH3, 8%), 368(M-3H2O, 28%), 353(M-3H2O-CH3, 10%), 289(M-H2O-SC, 10%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 86%), 226(M-3H2O-SC-part of ring D (27), 20%)(Ref. 0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)
Me ester-3,7,12-triacetate (70eV) m/z: 548(M, 1%), 488(M-AcOH, 3%), 428(M-2AcOH, 3%), 368(M-3AcOH, 48%), 313(M-SC, 42%), 253(100%), 211(18%), 413(3%), 353(21%), 286(6%), 281(9%), 274(4%), 271(3%), 261(7%), 226(20%)(Ref. 0231)
Me ester-3,7-diacetate (70eV) m/z: 506(M, 1%), 446(M-AcOH, 3%), 386(M-2AcOH, 10%), 313(M-SC, 38%), 253(100%), 211(14%), 428(24%), 413(3%), 368(38%), 353(14%), 286(10%), 281(14%), 271(14%), 261(21%), 226(14%)(Ref. 0231)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Widespread bile acid found in the biological fluids of most vertebrates.(Ref. 0001/0101)
Common primary bile acid.(Ref. 0100/0102)
Identified in urine and feces of healthy humans and patients with liver diseases.(Ref. 0150/0151/0162)
Identified in plasma of patients with bacterial overgrowth in the small intestine.(Ref. 0256)
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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[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]

[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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[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]

[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:
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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)
[TOP]

[0162]
AUTHOR:Eneroth, P., Gordon, B., and Sjovall, J.
TITLE:Characterization of trisubstituted cholanoic acids in human feces PubMed ID:5965294
JOURNAL:J Lipid Res.
VOL:7 PAGE : 524-530 (1966)
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[0231]
AUTHOR:Dias, J. R., and Nassim, B.
TITLE:Mass Spectra of Bile Acid Methyl Ester Acetate Derivatives.
JOURNAL:Org. Mass Spectrom.
VOL:13 PAGE : 402 -409 (1978)
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[0247]
AUTHOR:Kramer, W., and Kurz, G.
TITLE:Photolabile derivatives of bile salts. Synthesis and suitability for photoaffinity labeling PubMed ID:6631225
JOURNAL:J Lipid Res.
VOL:24 PAGE : 910-923 (1983)
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[0256]
AUTHOR:Setchell, K. D., Harrison, D. L., Gilbert, J. M., and Mupthy, G. M.
TITLE:Serum unconjugated bile acids: qualitative and quantitative profiles in ileal resection and bacterial overgrowth PubMed ID:4064336
JOURNAL:Clin Chim Acta.
VOL:152 PAGE : 297-306 (1985)
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