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Bile acid


DATA No : BBA0096 INFORMANT : Takashi Iida

NAME : 3a,7b,12a-Trihydroxy-5a-cholan-24-oic Acid

COMMON NAME: Alloursocholic Acid
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:269-271degC, (Me ester; mp, 166-167degC)(Ref. 0033/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +61.0deg(Ref. 0013/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1675(C=O), 3500, 1025, 1000(OH)(Ref. 0033)

NMR SPECTRA:1H-NMR (CDCl3+50%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 19-Me 0.74(s), 21-Me 0.97(d), 7a-H 3.24(brm), 3b- and 12b-H 3.88(m)(Ref. 0033)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.79(s), 21-Me 0.98(d), 7a-H 3.35(brm), COOMe 3.66(s), 3b- and 12b-H 4.00(m)(Ref. 0008/0033)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 31.9, C-2 28.8, C-3 65.7, C-4 35.4, C-5 36.1, C-6 38.2, C-7 74.6, C-8 43.4, C-9 45.1, C-10 34.8, C-11 28.4, C-12 72.1, C-13 47.1, C-14 47.4, C-15 26.2, C-16 27.6, C-17 45.7, C-18 12.6, C-19 10.9, C-20 34.8, C-21 17.2, C-22 30.9, C-23 30.8, C-24 174.4, C-25 51.1(Ref. 0011)

MASS SPECTRA:Me ester (20eV) m/z: 404(M-H2O, 2%), 386(M-2H2O, 22%), 289(M-H2O-SC, 96%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 22%)(Ref. 0012/0033)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Isolated from bile of patients with cerebrotendinous xanthomatosis.(Ref. 0178)
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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[0013]
AUTHOR:Mitra, M. N., and Elliott, W. H.
TITLE:Bile acids. XXIV. Raney nickel in the preparation of allocholanic acids PubMed ID:5742844
JOURNAL:J Org Chem.
VOL:33 PAGE : 2814-2818 (1968)
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[0033]
AUTHOR:Iida, T., Shinohara, T., Momose, T., Tamura, T., Matsumoto, T., Nambara, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites;12. Synthesis of Stereoisomeric 3,7,12-Trihydroxy-5a-cholanic Acids and Related Compounds.
JOURNAL:Synthesis
VOL: PAGE : 998 -1004 (1986)
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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)
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[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)
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[0178]
AUTHOR:Kihira, K., Shimazu, K., Kuwabara, M., Yoshii, M., Takeuchi, H., Nakano, I., Ozawa, S., Onuki, M., Hatta, Y., and Hoshita, T.
TITLE:Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis PubMed ID:3660436
JOURNAL:Steroids.
VOL:48 PAGE : 109-119 (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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