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Bile acid


DATA No : BBA0026 INFORMANT : Takashi Iida

NAME : 3b,6a-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:198-199degC, (Me ester; mp, 74-75degC)(Ref. 0018)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1702 (C=O), 3398, 1040 (OH)(Ref. 0018)

NMR SPECTRA:1H-NMR (CDCl3+30%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 21-Me 0.92(d), 19-Me 0.93(s), 6b-H 3.99(brm), 3a-H 4.09(m)(Ref. 0018)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 21-Me 0.91(d), 19-Me 0.94(s), 6b-H 4.10(brm), 3a-H 4.16(m)(Ref. 0018)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 30.0, C-2 27.5, C-3 66.0, C-4 26.3, C-5 43.0, C-6 67.8, C-7 34.6, C-8 34.6, C-9 39.1, C-10 36.4, C-11 21.0, C-12 40.0, C-13 42.9, C-14 56.2, C-15 24.1, C-16 28.0, C-17 56.0, C-18 12.0, C-19 23.9, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0018)

MASS SPECTRA:Me ester (70eV) m/z: 406(M+, 3%), 388 (M-H2O, 78%), 373(M-H2O-CH3, 24%), 370(M-2H2O, 23%), 355(M-2H2O-CH3, 11%), 273(M-H2O-SC, 13%)(Ref. 0018)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from pig bile.(Ref. 0101)
Metabolite of lithocholic acid in human fetal liver.(Ref. 0164)
Isolated from pig gallstone.(Ref. 0238)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0007]
AUTHOR:Lawson, A. M., and Setchell, K. D. R. (1988) Mass Spectrometry of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchall, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp 167-267, Plenum Press, New York.
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JOURNAL:
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[0018]
AUTHOR:Iida, T., Momose, T., Tamura, T., Matsumoto, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. 13. Improved routes to 3 beta, 6 beta- and 3 beta, 6 alpha-dihydroxy-5 beta-cholanoic acids PubMed ID:3367086
JOURNAL:J Lipid Res.
VOL:29 PAGE : 165-171 (1988)
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[0101]
AUTHOR:Matschiner, J. T. (1971) Naturally Occurring Bile Acids and Alcohols and their Origins. In The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1 : Chemistry) (Nair, P. P., and Krichevsky, D. eds), pp. 11-46, Plenum Press, New York.
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JOURNAL:
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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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[0238]
AUTHOR:Haslewood, G. A. D., and Wootton, V.
TITLE:Comparative Studies of `Bile Salts'.
JOURNAL:Biochem. J.
VOL:47 PAGE : 584 -597 (1950)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.