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Bile acid


DATA No : BBA0029 INFORMANT : Takashi Iida

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

COMMON NAME:
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:256-259degC, (Me ester; mp, 168-171degC)(Ref. 0019/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-21: +9.36deg (C=1.0, CHCl3+n-propqnol)(Ref. 0046/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1703 (C=O), 3435, 1026, 1009 (OH)(Ref. 0019)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.69(s), 21-Me 0.93(d), 19-Me 0.98(s), 6a-H 3.65(m), 3b-H 4.05(m)(Ref. 0019)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.656(s), 21-Me 0.886(d, 6.5), 19-Me 0.966(s), COOMe 3.628(s), 6a-H 3.707(dd,2.5, 5.0), 3b-H 4.136(brs)(Ref. 0019)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 34.03, C-2 29.16, C-3 66.71, C-4 33.15, C-5 41.76, C-6 72.28, C-7 39.78, C-8 30.37, C-9 54.22, C-10 36.15, C-11 20.67, C-12 39.97, C-13 42.78, C-14 56.26, C-15 24.23, C-16 28.14, C-17 55.94, C-18 12.19, C-19 14.92, C-20 35.45, C-21 18.35, C-22 31.07, C-23 31.15, C-24 174.88, C-25 51.56(Ref. 0019)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0019]
AUTHOR:Iida, T., Tamaru, T., Chang, F. C., Niwa, T., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. 20. A new synthetic route to stereoisomeric 3,6-dihydroxy- and 6-hydroxy-5 alpha-cholanoic acids PubMed ID:8212086
JOURNAL:Steroids.
VOL:58 PAGE : 362-369 (1993)
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[0046]
AUTHOR:Lehmann, G., Tepper, H. J., and Hilgetag, G.
TITLE:[Progesterone from 3-alpha-hydroxy-6-oxo-5-alpha-cholic acid] PubMed ID:5593873
JOURNAL:Justus Liebigs Ann Chem.
VOL:703 PAGE : 176-181 (1967)
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[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 : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.