Back to HOME

Bile acid


DATA No : BBA0066 INFORMANT : Takashi Iida

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

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


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:200-202degC, (Me ester; mp, 97-98degC)(Ref. 0029)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +35deg (C=0.514, MeOH)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1710 (C=O), 3400, 1045, 1018 (OH)(Ref. 0029)

NMR SPECTRA:1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 21-Me 0.94(d), 19-Me 1.08(s), 3b-H 3.40(brm), 6a- and 7b-H 3.69(m)(Ref. 0029)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.69(s), 21-Me 0.93(d), 19-Me 1.08(s), 3b-H 3.47-3.53(brm), COOMe 3.66(s), 6a-H 3.72(m), 7b-H 3.73(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.7, C-2 30.1, C-3 71.4, C-4 36.1, C-5 48.0, C-6 76.5, C-7 72.7, C-8 35.3, C-9 32.9, C-10 34.7, C-11 20.4, C-12 39.5, C-13 42.6, C-14 49.9, C-15 23.6, C-16 28.1, C-17 55.8, C-18 11.6, C-19 25.2, C-20 35.1, C-21 18.3, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0029)

MASS SPECTRA:Me ester (70eV) m/z: 422 (M+, 1%), 404(M-H2O, 41%), 368(M-2H2O, 60%), 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)
A primary bile acid in rodent.(Ref. 0102)
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 : - ()
[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 : - ()
[TOP]

[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 : - ()
[TOP]

[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 : - ()
[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:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[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.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.