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Bile acid


DATA No : BBA0044 INFORMANT : Takashi Iida

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

COMMON NAME: Allodeoxycholic Acid, b-Lagodeoxycholic Acid
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:220-221degC, (Me ester; mp, 179.0-180.5degC)(Ref. 0014/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-27: +42pm1deg (C=0.75, 90%EtOH), [a]d-23: +35.6pm1deg (C=1.0, MeOH) (Me ester)(Ref. 0001/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmaxcm-1: 1690 (C=O), 3350, 1060, 1013, 1003, 975, 955 (OH)(Ref. 0014)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.68(s), 19-Me 0.77(s), 21-Me 1.00(d), 3b- and 12b-H 3.95(m)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.79(s), 21-Me 0.98(d), COOMe 3.63(s), 3b- and 12b-H 3.96(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, 6%), 373(M-H2O-CH3, 2%), 357(M-H2O-CH3O, 4%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 40%), 249(M-SC-ring D (42), 2%), 213(M-2H2O-SC-42, 6%)(Ref. 0009/0012/0014)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Constituent of rabbit bile and faeces.(Ref. 0001/0101/0158)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
A major component of gallstones induced in the rabbit by 5-acholestan-3b-ol.(Ref. 0171)
Constituent of a urinary bile acid in late pregnancy and in recurrent cholestasis of pregnancy.(Ref. 0206)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Hill, R. A., Kirk, D. N., Makin, H. L. J., and Murphy, G. M. (1991) Chemical Data, Structures and Bibliographies, in Dictionary of Steroids, Chapman & Hall, London.
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)
[TOP]

[0009]
AUTHOR:Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[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]

[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)
[TOP]

[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.
TITLE:
JOURNAL:
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[0150]
AUTHOR:Alme, B., Bremmelgaard, A., Sjovall, J., and Thomassen, P.
TITLE:Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry PubMed ID:864325
JOURNAL:J Lipid Res.
VOL:18 PAGE : 339-362 (1977)
[TOP]

[0151]
AUTHOR:Bremmelgaard, A., and Sjovall, J.
TITLE:Bile acid profiles in urine of patients with liver diseases PubMed ID:118027
JOURNAL:Eur J Clin Invest.
VOL:9 PAGE : 341-348 (1979)
[TOP]

[0158]
AUTHOR:Danielsson, H., Kallner, A., and Sjövall, J.
TITLE:On the Composition of the Bile Acid Fraction of Rabbit Feces and the Isolation of a New Bile Acid: 3a,12a-Dihydroxy-5a-cholanic Acid.
JOURNAL:J. Biol. Chem.
VOL:238 PAGE : 3846 -3852 (1963)
[TOP]

[0171]
AUTHOR:Hofmann, A. F., and Mosbach, E. H.
TITLE:Identification Of Allodeoxycholic Acid As The Major Component Of Gallstones Induced In The Rabbit By 5-Alpha-Cholestan-3-Beta-Ol PubMed ID:14216431
JOURNAL:J Biol Chem.
VOL:239 PAGE : 2813-2821 (1964)
[TOP]

[0206]
AUTHOR:Thomassen, P. A.
TITLE:Urinary bile acids in late pregnancy and in recurrent cholestasis of pregnancy PubMed ID:119641
JOURNAL:Eur J Clin Invest.
VOL:9 PAGE : 425-432 (1979)
[TOP]

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