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Bile acid


DATA No : BBA0067 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:225-227degC(Ref. 0029)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-26: +64deg (C=0.528, MeOH)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1695 (C=O), 3425, 1052 (OH)(Ref. 0029)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 21-Me 0.94(d), 19-Me 1.08(s), 3b- and 7a-H 3.50(brm), 6a-H 3.61(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.69(s), 21-Me 0.93(d), 19-Me 1.10(s), 7a-H 3.55(dd, J, 9.8, 3.8), 3b-H 3.58-3.64(brm), COOMe 3.67(s), 6a-H 3.70(dd, J, 3.6, 2.5)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.4, C-2 29.9, C-3 70.9, C-4 35.4, C-5 47.2, C-6 75.4, C-7 73.5, C-8 38.5, C-9 39.6, C-10 33.8, C-11 20.8, C-12 39.9, C-13 43.7, C-14 54.9, C-15 27.0, C-16 28.4, C-17 55.5, C-18 12.0, C-19 25.4, C-20 35.2, C-21 18.4, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.4(Ref. 0029)
13C-NMR (Pyridine-d5; 50.309MHz) d: C1 36.51, C2 30.93, C3 70.83, C4 36.70, C5 48.67, C6 76.44, C7 73.34, C8 39.09, C9 40.37, C10 34.42, C11 21.44, C12 40.56, C13 43.92, C14 56.42, C15 27.80, C16 29.05, C17 55.60, C18 12.52, C19 26.31, C20 35.83, C21 18.91, C22 31.91, C23 31.91, C24 176.67(Ref. 0118)

MASS SPECTRA:Me ester (70eV) m/z: 422 (M+, 1%), 404(M-H2O, 100%), 368(M-2H2O, 62%), 371(M-2H2O-SC, 15%)(Ref. 0029)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from rats.(Ref. 0100/0101/0196/0215)
Primary bile acid in rodent.(Ref. 0102)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Isolated from serum, urine and duodenal fluid of a child with intrahepatic cholestasis.(Ref. 0173)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
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:
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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:
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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]

[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:
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[0118]
AUTHOR:Kayahara, T., Tamura, T., Amuro, Y., Higashino, K., Igimi, H., and Uchida, K.
TITLE:Delta 22-beta-muricholic acid in monoassociated rats and conventional rats PubMed ID:8177022
JOURNAL:Lipids.
VOL:29 PAGE : 289-296 (1994)
[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]

[0173]
AUTHOR:Huang, C. T. L., Leeuwent, P. S-V., Strickland, A., Calvin, R., and Nichols, B.L.
TITLE:Novel Bile Acids in Serum, Urine and Duodenal Fluid of a Child with Intrahepatic Cholestasis.
JOURNAL:Fed. Proc.
VOL:38 PAGE : 1118 - (1979)
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[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)
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[0196]
AUTHOR:Satoh, T., Uchida, K., Takase, H., Nomura, Y., and Takeuchi, N.
TITLE:Bile acid synthesis in young and old rats PubMed ID:15374163
JOURNAL:Arch Gerontol Geriatr.
VOL:23 PAGE : 1-11 (1996)
[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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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.