Back to HOME

Bile acid


DATA No : BBA0005 INFORMANT : Takashi Iida

NAME : 3a-Hydroxy-5a-cholan-24-oic Acid

COMMON NAME: Allolithocholic Acid
SYMBOL:
FORMULA: C24H40O3 MOL.WT (average) : 376.573


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:204-208degC, (Me ester; mp, 160-161degC)(Ref. 0001/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-26: +26.0deg, [a]d-26: +22.5pm1deg (C=0.85, CHCl3) (Me ester)(Ref. 0001/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmaxcm-1: 3225, 1736, 1275, 1034, 1002, 956, 894(Ref. 0013)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.77(s), 21-Me 0.91(d), 3b-H 4.00(m)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 32.1, C-2 28.9, C-3 66.3, C-4 35.8, C-5 39.0, C-6 28.5, C-7 31.9, C-8 35.4, C-9 54.2, C-10 35.9, C-11 20.7, C-12 39.9, C-13 42.5, C-14 56.4, C-15 24.0, C-16 28.0, C-17 55.8, C-18 12.0, C-19 11.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.3(Ref. 0011)

MASS SPECTRA:Me ester (20eV) m/z: 390(M+1, 61%), 375(M-CH3, 16%), 372(M-H2O, 85%), 357(M-H2O-CH3, 27%), 249(M-141, 14%), 248(M-SC-part of ring D (27), 57%), 233(M-SC-ring D (42), 90%), 230(M-H2O-SC-27, 15%), 217(M-173, 40%), 215(M-H2O-SC-42, 100%)(Ref. 0012)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from human faceces.(Ref. 0001)
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0150/0151)
Isolated from urine of infants with biliary atresia.(Ref. 0185)
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]

[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]

[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)
[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]

[0185]
AUTHOR:Makino, I., Sjovall, J., Norman, A., and Strandvik, B.
TITLE:Excretion of 3beta-hydroxy-5-cholenoic and 3a-hydroxy-5a-cholanoic acids in urine of infants with biliary atresia PubMed ID:11945837
JOURNAL:FEBS Lett.
VOL:15 PAGE : 161-164 (1971)
[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.