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Bile acid


DATA No : BBA0075 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:256-262degC, (Me ester; mp, 142-144degC)(Ref. 0001/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +49.5deg (C=0.417, MeOH)(Ref. 0001/0237)
[a]D: +47.9deg (Me ester)(Ref. 0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1710 (C=O), 3412, 1035 (OH)(Ref. 0037)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 19-Me 0.96(s), 7a-H 3.26(m), 6a-H 3.54(m), 3b-H 4.08(m)(Ref. 0037)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.671(s), 21-Me 0.902(d), 19-Me 0.953(s), 7a-H 3.296(dd,J, 3.8, 10.0), 6a-H 3.597(t, J, 3.1), COOMe 3.634(s), 3b-H 4.149(t, J, 2.3)(Ref. 0037)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 33.01, C-2 29.16, C-3 66.58, C-4 34.14, C-5 40.20, C-6 74.92, C-7 76.86, C-8 38.26, C-9 52.47, C-10 35.35, C-11 20.56, C-12 39.90, C-13 43.72, C-14 54.97, C-15 27.27, C-16 28.68, C-17 55.47, C-18 12.24, C-19 15.04, C-20 35.45, C-21 18.48, C-22 31.13, C-23 31.09, C-24 174.88, C-25 51.59(Ref. 0037)

MASS SPECTRA:Me ester (70eV) m/z: 404(M-H2O, 100%), 386(M-2H2O, 83%), 368(M-3H2O, 38%), 289(M-H2O-SC, 22%), 271(M-2H2O-SC, 19%), 262(M-H2O-SC-part of ring D (27), 71%), 253(M-3H2O-SC, 19%), 244(M-H2O-SC-27, 43%)(Ref. 0037)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

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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[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)
[TOP]

[0237]
AUTHOR:Elliott, W. H. (1971) Allo Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1: Chemistry) (Nair, P. P., and Kritchevsky, D. eds), pp47-93, 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.