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Bile acid


DATA No : BBA0065 INFORMANT : Takashi Iida

NAME : 3a,6a,7b-Trihydroxy-5b-cholan-24-oic Acid

COMMON NAME: w-Muricholic Acid
b-Hyocholic Acid
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:150-153degC and 184-188degC(Ref. 0001)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +36deg (C=0.38, MeOH)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1690 (C=O), 3400, 1045 (OH)(Ref. 0029)

NMR SPECTRA:1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 19-Me 0.93(s), 3b- and 7a-H 3.40(brm), 6b-H 3.68(brm)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz ) d: 18-Me 0.67(s), 21-Me 0.92(d), 19-Me 0.95(s), 7a-H 3.40(t, J, 9.4), 3b-H 3.55-3.61(brm), COOMe 3.67(s), 6b-H 3.79(dd, J, 9.3, 5.1)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.3, C-2 30.9, C-3 71.2, C-4 29.9, C-5 47.6, C-6 73.0, C-7 75.4, C-8 41.7, C-9 39.7, C-10 35.3, C-11 21.2, C-12 40.0, C-13 43.8, C-14 55.0, C-15 26.7, C-16 28.5, C-17 55.9, C-18 12.2, C-19 23.6, C-20 35.3, C-21 18.4, C-22 31.1, C-23 31.1, C-24 174.6, C-25 51.3(Ref. 0029)

MASS SPECTRA:Me ester (70eV) m/z: 422(M+, 7%), 404(M-H2O, 74%), 386(M-2H2O, 83%), 371(M-2H2O-CH3, 16%), 368(M-3H2O, 23%)(Ref. 0029)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
A bacterial biotransformation product in rat.(Ref. 0102)
Identified in urine of a patient with cerebrotendinous xanthomatosis, during oral administration of ursodeoxycholic acid.(Ref. 0124)
Identified in serum and urine of healthy humans and patients with liver diseases.(Ref. 0149/0150/0151/0163/0187/0193)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
A metabolite of hyodeoxycholic acid in the rat.(Ref. 0215)
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:
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[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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[0029]
AUTHOR:Iida, T., Momose, T., Tamura, T., Matsumoto, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers PubMed ID:2769078
JOURNAL:J Lipid Res.
VOL:30 PAGE : 1267-1279 (1989)
[TOP]

[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:
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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)
[TOP]

[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)
[TOP]

[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]

[0163]
AUTHOR:Goto, J., Hasegawa, K., Nambara, T., and Iida, T.
TITLE:Studies on steroids. CCLIV. Gas chromatographic-mass spectrometric determination of 4- and 6-hydroxylated bile acids in human urine with negative ion chemical ionization detection PubMed ID:1629271
JOURNAL:J Chromatogr.
VOL:574 PAGE : 1-7 (1992)
[TOP]

[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)
[TOP]

[0191]
AUTHOR:Nakagawa, M., Colombo, C., and Setchell, K. D.
TITLE:Comprehensive study of the biliary bile acid composition of patients with cystic fibrosis and associated liver disease before and after UDCA administration PubMed ID:2391071
JOURNAL:Hepatology.
VOL:12 PAGE : 322-334 (1990)
[TOP]

[0193]
AUTHOR:Nakashima, T., Sano, A., Seto, Y., Nakajima, T., Shima, T., Sakamoto, Y., Okuno, T., Kashima, K., and Hasegawa, T.
TITLE:Unusual trihydroxy bile acids in the urine of patients treated with chenodeoxycholate, ursodeoxycholate or rifampicin and those with cirrhosis PubMed ID:2307404
JOURNAL:Hepatology.
VOL:11 PAGE : 255-260 (1990)
[TOP]

[0215]
AUTHOR:Hsia, S. L. (1971) Hyocholic Acid and Muricholic Acid, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1 : Chemistry) (Nair, P. P. and Krichevsky, D., eds), pp95-120, Plenum Press, New York.
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JOURNAL:
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.