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Bile acid


DATA No : BBA0090 INFORMANT : Takashi Iida

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

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:164.5-165.5degC(Ref. 0031)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1730 (C=O), 3636, 3509, 1031, 1020, 990, 954 (OH)(Ref. 0031)

NMR SPECTRA:1H-NMR (CDCl3+10%DMSO-d6+D2O; 100MHz) d: 18-Me 0.70(s), 19-Me 0.94(s), 7a-H 3.56(brm), 3a- and 12b-H 3.96(m)(Ref. 0031)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.71(s), 19-Me 0.96(s),7a-H 3.58(brm), COOMe 3.64(s), 12b-H 3.9(m), 3a-H 4.06(m)(Ref. 0005/0031)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 29.3, C-2 27.7, C-3 66.2 C-4 34.3, C-5 36.9, C-6 36.6, C-7 71.0, C-8 43.5, C-9 31.2, C-10 33.9, C-11 29.2, C-12 72.2, C-13 47.5, C-14 47.2, C-15 26.1, C-16 27.4, C-17 45.8, C-18 12.6, C-19 23.4, C-20 34.8, C-21 17.2, C-22 30.9, C-23 30.8, C-24 174.5, C-25 51.3(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 402(M-H2O, 1%), 386(M-2H2O, 14%), 371(M-2H2O-CH3, 4%), 368(M-3H2O, 3%), 353(M-3H2O-CH3, 2%), 289(M-H2O-SC, 53%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 32%), 226(M-3H2O-SC-part of ring D (27), 2%)(Ref. 0010)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected as a component of human feces.(Ref. 0101/0162)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)
Identified in urine of infants during the first year.(Ref. 0210)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0005]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:24 PAGE : 163 -165 (1983)
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[0006]
AUTHOR:Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C.
TITLE:Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers.
JOURNAL:Org. Magn. Reson.
VOL:21 PAGE : 305 -309 (1983)
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[0010]
AUTHOR:Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T.
TITLE:High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids.
JOURNAL:Biomed. Mass Spectrom.
VOL:9 PAGE : 473 -476 (1982)
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[0031]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. 7. 3,7,12-Trihydroxy-5b-cholanic Acids.
JOURNAL:J. Org. Chem.
VOL:47 PAGE : 2972 -2978 (1982)
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[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:
VOL: PAGE : - ()
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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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[0162]
AUTHOR:Eneroth, P., Gordon, B., and Sjovall, J.
TITLE:Characterization of trisubstituted cholanoic acids in human feces PubMed ID:5965294
JOURNAL:J Lipid Res.
VOL:7 PAGE : 524-530 (1966)
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[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)
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[0210]
AUTHOR:Wahlen, E., and Strandvik, B.
TITLE:Effects of different formula feeds on the developmental pattern of urinary bile acid excretion in infants PubMed ID:8126625
JOURNAL:J Pediatr Gastroenterol Nutr.
VOL:18 PAGE : 9-19 (1994)
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