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Bile acid


DATA No : BBA0082 INFORMANT : Takashi Iida

NAME : 3b,6a,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:135-137degC, (Me ester; mp, 115-117degC)(Ref. 0030)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1709 (C=O), 3412, 1036, 976 (OH)(Ref. 0030)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.67(s), 19-Me 0.92(s), 21-Me 0.96(d), 12b-H 3.96(m), 6b-H 4.00(brm), 3a-H 4.08(m)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.680(s), 19-Me 0.929(s), 21-Me 0.973(d), COOMe 3.664(s), 12b-H 3.993(m), 6b-H 4.119(brm), 3a-H 4.156(m)(Ref. 0030)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 30.08, C-2 27.43, C-3 66.09, C-4 26.25, C-5 43.05, C-6 67.85, C-7 34.37, C-8 34.93, C-9 32.33, C-10 36.05, C-11 28.93, C-12 73.04, C-13 46.75, C-14 48.12, C-15 23.67, C-16 27.43, C-17 47.42, C-18 12.78, C-19 23.84, C-20 35.13, C-21 17.40, C-22 31.12, C-23 30.93, C-24 174.78, C-25 51.59(Ref. 0030)

MASS SPECTRA:Me ester (70eV) m/z: 404(M-H2O, 6%), 386(M-2H2O, 42%), 289(M-H2O-SC, 79%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 39%)(Ref. 0030)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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.