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Bile acid


DATA No : BBA0037 INFORMANT : Takashi Iida

NAME : 3a,7b-Dihydroxy-5a-cholan-24-oic Acid

COMMON NAME: Alloursodeoxycholic Acid
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:243.5-245degC(Ref. 0023/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1677(C=O), 3300, 1032, 1003 (OH)(Ref. 0023)
Me ester: nmax cm-1: 1735(C=O), 3430, 1032, 1003 (OH)(Ref. 0023)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.78(s), 21-Me 0.93(d), 7a-H 3.40(brm), 3b-H 3.95 (m)(Ref. 0023)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.79(s), 21-Me 0.93(d), 7a-H 3.34(brm), COOMe 3.65(s), 3b-H 4.05 (m)(Ref. 0008/0023)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.2, C-2 29.0, C-3 65.9, C-4 35.7, C-5 36.4, C-6 38.4, C-7 74.9, C-8 43.6, C-9 52.8, C-10 35.4, C-11 20.9, C-12 40,0, C-13 43.6, C-14 56.0, C-15 26.8, C-16 28.3, C-17 55.2, C-18 12.1, C-19 11.1, C-20 35.1, C-21 18.3, C-22 31.1, C-23 31.1, C-24 174.1, C-25 50.9(Ref. 0011)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 64%), 373(M-H2O-CH3, 14%), 370(M-2H2O, 100%), 355(M-2H2O-CH3, 36%), 255(M-2H2O-SC, 64%), 249(M-SC-ring D (42), 25%), 246(M-H2O-SC-part of ring D (27), 22%)(Ref. 0012/0023)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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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[0023]
AUTHOR:Iida, T., Momose, T., Nambara, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. X. Syntheses of Stereoisomeric 3,7-Dihydroxy-5a-cholanic Acids.
JOURNAL:Chem. Pharm. Bull.
VOL:34 PAGE : 1929 -1933 (1986)
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[0237]
AUTHOR:Elliott, W. H. (1971) Allo Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1: Chemistry) (Nair, P. P., and Kritchevsky, D. eds), pp47-93, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.