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Bile acid


DATA No : BBA0035 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:166.0-168.5degC, (Me ester; mp, 124.0-125.0degC)(Ref. 0021)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +56deg (MeOH)(Ref. 0073)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1709 (C=O), 1031, 1061 (OH)(Ref. 0021)

NMR SPECTRA:1H-NMR (CDCl3; 100MHz) d: 18-Me 0.71(s), 19-Me 1.00(s), 7a-H 3.65(brm), 3a-H 4.07(m)(Ref. 0005/0021)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.71(s), 19-Me 1.00(s), 7a-H 3.55(brm), COOMe 3.65(s), 3a-H 4.04(m)(Ref. 0021)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.3, C-2 27.2, C-3 65.7, C-4 34.1, C-5 36.7, C-6 36.5, C-7 70.7, C-8 43.0, C-9 38.2, C-10 34.1, C-11 21.1, C-12 39.8, C-13 43.2, C-14 55.6, C-15 26.5, C-16 28.2, C-17 54.5, C-18 11.7, C-19 23.5, C-20 34.8, C-21 18.0, C-22 30.6, C-23 30.6, C-24 174.2, C-25 51.0(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 100%), 373(M-H2O-CH3, 41%), 370(M-2H2O, 34%), 357(M-H2O-CH3O, 13%), 355(M-2H2O-CH3, 24%), 273(M-H2O-SC, 9%), 264(M-SC-part of ring D (27), 27%), 255(M-2H2O-SC, 40%), 249(M-SC-ring D (42), 25%), 246(M-H2O-SC-27, 38%), 228(M-2H2O-SC-27, 17%), 213(M-2H2O-SC-42, 57%)(Ref. 0010)
Me-TMS ether (70eV) m/z: 535(M-CH3, 1%), 460(M-TMSOH, 37%), 370(M-2TMSOH, 100%), 355(42%), 255(27%), 73(32%)(Ref. 0007/0049)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in serum and urine from patients with primary biliary cirrhosis.(Ref. 0149/0184/0187)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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)
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[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:
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]

[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]

[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)
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[0073]
AUTHOR:Riva, S., Bovara, R., Zetta, L., Pasta, P., Ottolina, G., and Carrea, G.
TITLE:Enzymatic a/b Inversion of C-3 Hydroxyl of Bile Acids and Study of the Effects of Organic Solvents on Reaction Rates.
JOURNAL:J. Org. Chem.
VOL:53 PAGE : 88 -92 (1988)
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[0124]
AUTHOR:Koopman, B. J., Wolthers, B. G., van der Molen, J. C., Nagel, G. T., and Kruizinga, W.
TITLE:Abnormal urinary bile acids in a patient suffering from cerebrotendinous xanthomatosis during oral administration of ursodeoxycholic acid PubMed ID:3801500
JOURNAL:Biochim Biophys Acta.
VOL:917 PAGE : 238-246 (1987)
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[0149]
AUTHOR:Batta, A. K., Arora, R., Salen, G., Tint, G. S., Eskreis, D., and Katz, S.
TITLE:Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment PubMed ID:2621422
JOURNAL:J Lipid Res.
VOL:30 PAGE : 1953-1962 (1989)
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[0184]
AUTHOR:Maeda, M., Ohama, H., Takeda, H., Yabe, M., Nambu, M., and Namihisa, T.
TITLE:Identification of 3 beta, 7 beta-dihydroxy-5 beta-cholan-24-oic acid in serum from patients treated with ursodeoxycholic acid PubMed ID:6707518
JOURNAL:J Lipid Res.
VOL:25 PAGE : 14-26 (1984)
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[0187]
AUTHOR:Marschall, H. U., Matern, H., Wietholtz, H., Egestad, B., Matern, S., and Sjovall, J.
TITLE:Bile acid N-acetylglucosaminidation. In vivo and in vitro evidence for a selective conjugation reaction of 7 beta-hydroxylated bile acids in humans PubMed ID:1602004
JOURNAL:J Clin Invest.
VOL:89 PAGE : 1981-1987 (1992)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.