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Bile acid


DATA No : BBA0033 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:203.4-205.0degC, (Me ester; mp, 159-161degC)(Ref. 0022)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-30: +44.5deg (C=2.0, EtOH)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1709 (C=O), 1050, 1010 (OH)(Ref. 0022)

NMR SPECTRA:Me ester 1H-NMR (CDCl3+10%DMSO-d6; 100MHz) d: 18-Me 0.69(s), 19-Me 0.96(s), 3b- and 7a-H 3.55(brm), COOMe 3.65(s)(Ref. 0005/0021)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 34.8, C-2 30.1, C-3 70.9, C-4 37.2, C-5 42.4, C-6 37.0, C-7 70.9, C-8 43.4, C-9 39.2, C-10 33.9, C-11 21.1, C-12 40,1, C-13 43.6, C-14 55.8, C-15 26.8, C-16 28.4, C-17 54.9, C-18 12.0, C-19 23.3, C-20 35.1, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.5, C-25 51.3(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 58%), 370(M-2H2O, 94%), 355(M-2H2O-CH3, 44%), 273(M-H2O-SC, 28%), 264(M-SC-part of ring D (27), 14%), 255(M-2H2O-SC, 100%), 249(M-SC-ring D (42), 14%), 246(M-H2O-SC-27, 44%), 228(M-2H2O-SC-27, 33%), 213(M-2H2O-SC-42, 61%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 535(M-CH3, 3%), 460(M-TMSOH, 100%), 370(M-2TMSOH, 63%), 355(38%), 255(47%), 73(31%)(Ref. 0007/0049)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Occurred in bear bile.(Ref. 0001/0101)Cholagogic agent used for dissolution of gallstones.(Ref. 0001/0101)
Primary bile acid in bear and nutria.(Ref. 0100/0102)
Identified in urine and feces of healthy humans and patients with liver diseases.(Ref. 0150/0151/0161)
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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[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]

[0021]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. 6. Stereoisomeric 3,7-Dihydroxy-5b-cholanic Acids.
JOURNAL:J. Org. Chem.
VOL:47 PAGE : 2966 -2972 (1982)
[TOP]

[0022]
AUTHOR:Iida, T., Taneja, H. R., and Chang, F. C.
TITLE:Potential bile acid metabolites: IV. Inversion of 7 alpha-hydroxyl; ursodeoxycholic acid PubMed ID:7311744
JOURNAL:Lipids.
VOL:16 PAGE : 863-865 (1981)
[TOP]

[0049]
AUTHOR:Batta, A. K., Aggarwal, S. K., Salen, G., and Shefer, S.
TITLE:Selective reduction of oxo bile acids: synthesis of 3 beta-, 7 beta-, and 12 beta-hydroxy bile acids PubMed ID:1940629
JOURNAL:J Lipid Res.
VOL:32 PAGE : 977-983 (1991)
[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:
VOL: PAGE : - ()
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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]

[0161]
AUTHOR:Eneroth, P., Gordon, B., Ryhage, R., and Sjovall, J.
TITLE:Identification of mono- and dihydroxy bile acids in human feces by gas-liquid chromatography and mass spectrometry PubMed ID:5966634
JOURNAL:J Lipid Res.
VOL:7 PAGE : 511-523 (1966)
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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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