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Bile acid


DATA No : BBA0046 INFORMANT : Takashi Iida

NAME : 3b,12a-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:228.5-229.5degC, (Me ester; mp, 140-142degC)(Ref. 0014/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: +38deg (MeOH)(Ref. 0001/0237)
[a]d-25: +35.2pm1deg (C=0.33, MeOH) (Me ester)(Ref. 0038/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxcm-1: 1715(C=O), 3530, 1042, 1017, 982, 958(OH)(Ref. 0014)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6) d: 18-Me 0.68(s), 19-Me 0.80(s), 21-Me 1.00(d), 3a-H 3.52(brm), 12b-H 3.92(m)(Ref. 0014)
Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.71(s), 19-Me 0.82(s), 21-Me 0.98(d), 3a-H 3.57(brm) COOMe 3.65(s) 12b-H 3.97(m)(Ref. 0008/0014)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.7, C-2 31.5, C-3 70.8, C-4 37.9, C-5 44.6, C-6 28.4, C-7 31.2, C-8 35.5, C-9 47.2, C-10 34.9, C-11 28.7, C-12 72.8, C-13 46.2, C-14 47.9, C-15 23.4, C-16 27.1, C-17 47.0, C-18 12.5, C-19 12.0, C-20 34.9, C-21 17.1, C-22 30.9, C-23 30.7, C-24 174.4, C-25 51.2(Ref. 0011/0014)

MASS SPECTRA:Me ester (70eV) m/z: 388(M-H2O, 5%), 273(M-H2O-SC, 100%), 255(M-2H2O-SC, 28%), 249(M-SC-ring D (42), 4%), 213(M-2H2O-SC-42, 5%)(Ref. 0009/0012/0014)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
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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[0007]
AUTHOR:Lawson, A. M., and Setchell, K. D. R. (1988) Mass Spectrometry of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchall, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp 167-267, Plenum Press, New York.
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]

[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]

[0038]
AUTHOR:Mitra, M. N., and Elliott, W. H.
TITLE:Bile acids. 23. A new direct synthesis of allocholic acid and its 3 beta isomer PubMed ID:5634890
JOURNAL:J Org Chem.
VOL:33 PAGE : 175-181 (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]

[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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