Back to HOME

Bile acid


DATA No : BBA0036 INFORMANT : Takashi Iida

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

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


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:245-246degC, (Me ester; mp, 125-127degC)(Ref. 0023/0024/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +6.38deg (C=1.0, MeOH)(Ref. 0001/0237)
[a]D: +6.4deg (Me ester)(Ref. 0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1702 (C=O), 3402, 1030, 1003 (OH)(Ref. 0023/0024)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO; 90MHz) d: 18-Me 0.65(s), 19-Me 0.76(s), 21-Me 0.92(d), 7b-H 3.75(m), 3b-H 3.97(m)(Ref. 0023/0024)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.78(s), 21-Me 0.92(d), COOMe 3.66(s), 7b-H 3.83(m), 3b-H 4.05(m)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.2, C-2 29.1, C-3 66.4, C-4 35.9, C-5 31.8, C-6 36.6, C-7 68.0, C-8 39.8, C-9 46.2, C-10 36.4, C-11 20.7, C-12 39.9, C-13 42.9, C-14 50.8, C-15 23.6, C-16 28.0, C-17 56.2, C-18 11.9, C-19 10.1, C-20 35.4, C-21 18.4, C-22 31.2, C-23 31.2, C-24 174.3, C-25 51.1(Ref. 0011)

MASS SPECTRA:Me ester (70eV) m/z: 406(M+, 3%), 388(M-H2O, 73%), 373(M-H2O-CH3, 17%), 370(M-2H2O, 19%), 355(M-2H2O-CH3, 12%), 273(M-H2O-SC, 66%), 264(M-SC-part of ring D (27), 29%), 249(M-SC-ring D (42), 32%), 246(M-H2O-SC-27, 37%), 228(M-2H2O-SC-27, 32%), 213(M-2H2O-SC-42, 40%)(Ref. 0009/0012/0023/0024)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
A metabolite of 5a-cholestan-3b-ol in the hyperthyroid rat.(Ref. 0041)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Identified in biliary bile of patients with cystic fibrosis.(Ref. 0191)
Constituent of a urinary bile acid in late prenancy 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 : - ()
[TOP]

[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]

[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)
[TOP]

[0024]
AUTHOR:Iida, T., Nishida, S., Chang, F. C., Niwa, T., Goto, J., and Nambara, T.
TITLE:Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids.
JOURNAL:Chem. Pharm. Bull
VOL:41 PAGE : 763 -765 (1993)
[TOP]

[0041]
AUTHOR:Ziller, S. A., Jr., Doisy, E. A., Jr., and Elliott, W. H.
TITLE:Bile acids. XXV. Allochenodeoxycholic acid, a metabolite of 5 alpha-cholestan-3 beta-ol in the hyperthyroid rat PubMed ID:5715510
JOURNAL:J Biol Chem.
VOL:243 PAGE : 5280-5288 (1968)
[TOP]

[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]

[0191]
AUTHOR:Nakagawa, M., Colombo, C., and Setchell, K. D.
TITLE:Comprehensive study of the biliary bile acid composition of patients with cystic fibrosis and associated liver disease before and after UDCA administration PubMed ID:2391071
JOURNAL:Hepatology.
VOL:12 PAGE : 322-334 (1990)
[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:
VOL: PAGE : - ()
[TOP]

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