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Bile acid


DATA No : BBA0021 INFORMANT : Takashi Iida

NAME : 2b,3a-Dihydroxy-5b-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:193-196degC, (Me ester; mp, 164-166degC)(Ref. 0015)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1715 (C=O), 3364, 1001 (OH)(Ref. 0015)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.64(s), 19-Me 0.94(s), 2a- and 3b-H 3.33(brm)(Ref. 0015)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.64(s), 19-Me 0.96(s), 21-Me 0.91(d), COOMe 3.66(s), 2a-H 3.52(brm), 3b-H 3.42(brm)(Ref. 0015)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 43.27, C-2 71.53, C-3 76.85, C-4 34.18, C-5 42.10, C-6 26.50, C-7 26.41, C-8 35.90, C-9 42.07, C-10 37.23, C-11 21.12, C-12 40.13, C-13 42.76, C-14 56.44, C-15 24.21, C-16 28.23, C-17 55.99, C-18 12.10, C-19 23.41, C-20 35.43, C-21 18.33, C-22 31.14, C-23 31.04, C-24 174.88, C-25 51.58(Ref. 0015)

MASS SPECTRA:Me-TMS ether (20eV) m/z: 550(M+), 460(M-90), 406, 371 (M-90-89, 100%), 330(Ref. 0015)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Metabolite of lithocholic acid in human fetal liver; : stereochemistry of a hydroxyl groups at C-2 is unidentified.(Ref. 0164)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0015]
AUTHOR:Iida, T., Komatsubara, I., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. 17. Synthesis of 2 beta-hydroxylated bile acids PubMed ID:2042229
JOURNAL:Steroids.
VOL:56 PAGE : 114-122 (1991)
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[0164]
AUTHOR:Gustafsson, J., Anderson, S., and Sjovall, J.
TITLE:Bile acid metabolism during development: metabolism of lithocholic acid in human fetal liver PubMed ID:3797138
JOURNAL:Pediatr Res.
VOL:21 PAGE : 99-103 (1987)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.