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Bile acid


DATA No : BBA0119 INFORMANT : Takashi Iida

NAME : 3a,6a,7b,12a-Tetrahydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O6 MOL.WT (average) : 424.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:148-151degC, (Me ester; mp, 100-102degC)(Ref. 0034)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1708(C=O), 3421, 1040, 952 (OH)(Ref. 0034)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 19-Me 0.90(s), 21-Me 0.98(d), 3b- and 7b-H 3.34(brm), 6a-H 3.60(brm), 12b-H 3.87(m)(Ref. 0034)
Me ester 1H-NMR (CDCl3; 400MHz) d: 18-Me 0.70(s), 19-Me 0.95(s), 21-Me 0.98(d), 7a-H 3.45(t, J, 9.6), 3b-H 3.57(brm), COOMe 3.67(s), 6b-H 3.78(dd, J, 9.6, 5.2), 12b-H 3.99(t, J, 4.3)(Ref. 0034/0035)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.38, C-2 29.72, C-3 71.28, C-4 30.45, C-5 47.82, C-6 73.28, C-7 75.25, C-8 41.82, C-9 32.15, C-10 34.97, C11 28.90, C12 72.52, C-13 47.53, C-14 45.98, C-15 26.36, C-16 27.99, C-17 47.42, C-18 12.89, C-19 23.40, C-20 35.24, C-21 17.38, C-22 31.04, C-23 31.21, C-24 174.97, C-25 51.62(Ref. 0034/0035)

MASS SPECTRA:Me ester (70eV) m/z: 402(M-2H2O, 24%), 384(M-3H2O, 26%), 366(M-4H2O, 6%), 305(M-H2O-SC, 69%), 287(M-2H2O-SC, 35%), 269(M-3H2O-SC, 82%), 251(M-4H2O-SC, 22%)(Ref. 0034)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

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.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0034]
AUTHOR:Iida, T., Komatsubara, I., Yoda, S., Goto, J., Nambara, T., and Chang, F. C.
TITLE:Potential bile acid metabolites. 16. Synthesis of stereoisomeric 3 alpha,6,7,12 alpha-tetrahydroxy-5 beta-cholanoic acids PubMed ID:2089743
JOURNAL:Steroids.
VOL:55 PAGE : 530-539 (1990)
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[0035]
AUTHOR:Iida, T., Chang, F. C., Mushiake, K., Goto, J., and Nambara, T.
TITLE:Complete 1H and 13C Resonance Assignments of Stereoisomeric 3a,6,7,12a-Tetrahydroxycholanoic Acids by Two-Dimensional Shift-Correlated NMR
JOURNAL:Mage. Reson. Chem.
VOL:31 PAGE : 645 -651 (1993)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.