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Bile acid


DATA No : BBA0054 INFORMANT : Takashi Iida

NAME : 7a,12b-Dihydroxy-5a-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:168-170degC, (Me ester; mp, 147.5-148.0degC)(Ref. 0028)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1708(C=O), 3425, 1032, 1015(OH)(Ref. 0028)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.68(s), 19-Me 0.77(s), 21-Me 1.02(d), 12a-H 3.27(brm), 7b-H 3.74(m)(Ref. 0028)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.72(s), 19-Me 0.79(s), 21-Me 1.01(d), 12a-H 3.39(brm), COOMe 3.66(s), 7b-H 3.83(m)(Ref. 0008/0028)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 38.3, C-2 21.9, C-3 26.5, C-4 28.4, C-5 39.1, C-6 36.8, C-7 67.6, C-8 38.2, C-9 45.2, C-10 36.2, C-11 29.5, C-12 78.9, C-13 47.6, C-14 48.7, C-15 23.0, C-16 23.9, C-17 57.2, C-18 7.6, C-19 10.9, C-20 32.7, C-21 20.9, C-22 32.1, C-23 31.0, C-24 174.6, C-25 51.3(Ref. 0011)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 5%), 370(M-2H2O, 18%), 355(M-2H2O-CH3O, 8%), 273(M-H2O-SC, 35%), 255(M-2H2O-SC, 100%)(Ref. 0012/0028)

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)
[TOP]

[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)
[TOP]

[0028]
AUTHOR:Iida, T., Momose, T., Chang, F. C., and Nambara, T.
TITLE:Potential Bile Acid Metabolites. XI. Syntheses of Stereoisomeric 7,12-Dihydroxy-5a-cholanoic Acids.
JOURNAL:Chem. Pharm. Bull.
VOL:34 PAGE : 1934 -1938 (1986)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.