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Bile acid


DATA No : BBA0083 INFORMANT : Takashi Iida

NAME : 3b,6b,12a-Trihydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:131-133degC, (Me ester; mp, 196-197degC)(Ref. 0030)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1709 (C=O), 3408, 1023 (OH)(Ref. 0030)Me ester: nmax m: 9.31, 9.64, 9.85, 10.21, 10.54(Ref. 0003)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.70(s), 21-Me 0.98(d), 19-Me 1.11(s), 6a-H 3.66(m), 3a- and 12b-H 3.99(m)(Ref. 0030)
Me ester 1H-NMR (CDCl3+20%DMSO-d6; 500MHz) d: 18-Me 0.686(s), 21-Me 0.983(d), 19-Me 1.101(s), COOMe 3.640(s), 6a-H 3.602(m), 12b-H 3.925(m), 3a-H 3.973(m)(Ref. 0030)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 29.43, C-2 26.50, C-3 64.44 C-4 32.24, C-5 42.23, C-6 71.38, C-7 33.42, C-8 29.91, C-9 32.86, C-10 33.48, C-11 28.04, C-12 71.58, C-13 45.57, C-14 47.05, C-15 22.86, C-16 26.64, C-17 45.84, C-18 11.91, C-19 24.99, C-20 34.37, C-21 16.36, C-22 30.09, C-23 29.91, C-24 173.65, C-25 50.49(Ref. 0030)

MASS SPECTRA:Me ester (70eV) m/z: 404(M-H2O, 2%), 386(M-2H2O, 18%), 289(M-H2O-SC, 14%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 19%)(Ref. 0030)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0003]
AUTHOR:Levin, S. J., and Johnston, C. G.
TITLE:Infrared Correlations in the Bile Acid Series
JOURNAL:Talanta.
VOL:8 PAGE : 871 -879 (1961)
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[0030]
AUTHOR:Iida, T., Tamaru, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. XVIII. Synthesis of stereoisomeric 3,6,12 alpha-trihydroxy-5 beta-cholanoic acids PubMed ID:1856610
JOURNAL:J Lipid Res.
VOL:32 PAGE : 649-658 (1991)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.