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Bile acid


DATA No : BBA0073 INFORMANT : Takashi Iida

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

COMMON NAME: Allo-w-muricholic Acid
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:242-244degC, (Me ester; mp, 192-193degC)(Ref. 0037)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +19.9deg (C=0.70, MeOH) (Me ester)(Ref. 0036)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1686 (C=O), 3481, 1007 (OH)(Ref. 0037)

NMR SPECTRA:1H-NMR (CDCl3+DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.79(s), 21-Me 0.93(s), 21-Me 0.93(d), 6b- and 7a-H 3.02(brm), 3b-H 4.00(m)(Ref. 0037)
Me ester 1H-NMR (CDCl3 +10%MeOH-d6; 500MHz) d: 18-Me 0.689(s), 19-Me 0.820(s), 21-Me 0.934(d), 6b- and 7a-H 3.085(m), COOMe 3.674(s), 3b-H 4.077(brs)(Ref. 0037)
Me ester 13C-NMR (CDCl3 +10%MeOH-d6; 125.65MHz) d: C-1 32.62, C-2 28.66, C-3 65.76, C-4 30.06, C-5 42.10, C-6 75.27, C-7 80.64, C-8 40.95, C-9 52.37, C-10 36.25, C-11 20.96, C-12 40.02, C-13 43.63, C-14 55.11, C-15 26.84, C-16 28.09, C-17 56.18, C-18 12.25, C-19 12.54, C-20 35.50, C-21 18.47, C-22 31.20, C-23 31.27, C-24 175.56, C-25 51.73(Ref. 0037)

MASS SPECTRA:Me ester (70eV) m/z: 404(M-H2O, 54%), 386(M-2H2O, 100%), 368(M-3H2O, 48%), 289(M-H2O-SC, 34%), 271(M-2H2O-SC, 49%), 262(M-H2O-SC-part of ring D (27), 21%), 253(M-3H2O-SC, 20%), 244(M-H2O-SC-27, 36%)(Ref. 0037)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from rat bile.(Ref. 0001)
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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[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]

[0036]
AUTHOR:Kelsey, M. I., Mui, M. M., and Elliott, W. H.
TITLE:Bile acids. 33. The synthesis of allomuricholic acids PubMed ID:5149002
JOURNAL:Steroids.
VOL:18 PAGE : 261-279 (1971)
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[0037]
AUTHOR:Iida, T., Nishida, S., Chang, F. C., Niwa, T., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. 19. The epimeric 3 alpha,6,7 beta-trihydroxy- and 3 alpha,6,7 beta,12 alpha-tetrahydroxy-5 alpha-cholanoic acids PubMed ID:8493703
JOURNAL:Steroids.
VOL:58 PAGE : 148-152 (1993)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.