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Bile acid


DATA No : BBA0045 INFORMANT : Takashi Iida

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

COMMON NAME: Allo-isodeoxycholic Acid
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:206.5-207.5degC, (Me ester; mp, 143-144degC)(Ref. 0014)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1680(C=O), 3440, 1050, 1028, 1013, 1000, 970(OH)(Ref. 0014)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.72(s), 19-Me 0.79(s), 21-Me 1.03(d), 12a-H 3.39(brm), 3b-H 3.99(m)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d : 18-Me 0.73(s), 19-Me 0.79(s), 21-Me 1.01(d), 12a-H 3.37(brm), COOMe 3.65(s), 3b-H 4.01(m)(Ref. 0008/0014)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.1, C-2 28.8, C-3 66.2, C-4 35.7, C-5 38.9, C-6 28.4, C-7 32.1, C-8 34.1, C-9 53.0, C-10 35.8, C-11 29.4, C-12 79.3, C-13 47.7, C-14 54.4, C-15 23.4, C-16 23.8, C-17 57.2, C-18 7.8, C-19 11.0, C-20 32.6, C-21 20.8, C-22 31.4, C-23 31.1, C-24 174.5, C-25 51.3(Ref. 0011/0014)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 9%), 357(M-H2O-CH3O, 5%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 57%), 249(M-SC-ring D (42), 7%), 213(M-2H2O-SC-42, 6%)(Ref. 0012/0014)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in feces of patients with cororectal cancer or polyps.(Ref. 0243)
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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[0008]
AUTHOR:Iida, T., and Shinohara, T.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part2. Mono-, Di- and Trisubstituted Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:28 PAGE : 175 -179 (1987)
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[0011]
AUTHOR:Iida, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Carbon-13 Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part II. Mono-, Di- and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:Chem. Phys. Lipids
VOL:45 PAGE : 1 -12 (1987)
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[0012]
AUTHOR:Iida, T., Tamura, T., and Matsumoto, T.
TITLE:Mass Spectra of Mono-, Di-, and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:29 PAGE : 279 -288 (1988)
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[0014]
AUTHOR:Iida, T., Tamura, T., Matsumoto, T., and Chang, F. C.
TITLE:Potential bile acid metabolites. 9. 3,12-Dihydroxy- and 12 beta-hydroxy-5 alpha-cholanoic acids PubMed ID:4031665
JOURNAL:J Lipid Res.
VOL:26 PAGE : 874-881 (1985)
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[0243]
AUTHOR:Imray, C. H., Radley, S., Davis, A., Barker, G., Hendrickse, C. W., Donovan, I. A., Lawson, A. M., Baker, P. R., and Neoptolemos, J. P.
TITLE:Faecal unconjugated bile acids in patients with colorectal cancer or polyps PubMed ID:1427378
JOURNAL:Gut.
VOL:33 PAGE : 1239-1245 (1992)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.