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Bile acid


DATA No : BBA0081 INFORMANT : Takashi Iida

NAME : 3a,6b,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:137-139degC(Ref. 0030)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-26: +36deg (C=0.406, 95%EtOH)(Ref. 0216)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1711 (C=O), 3401, 1045 (OH)(Ref. 0030)

NMR SPECTRA:1H-NMR (CDCl3; 90MHz)d: 18-Me 0.71(s), 21-Me 0.98(d), 19-Me 1.09(s), 3b-H 3.62(brm), 6a-H 3.62(m), 12b-H 3.98(m)(Ref. 0030)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.712(s), 19-Me 1.099(s), 21-Me 0.976(d), 3b-H 3.598(brm), COOMe 3.665(s), 6a-H 3.776(m), 12b-H 4.006(m)(Ref. 0030)
Me ester 13C-NMR (CDCl3; 125.65MHz) d: C-1 35.76, C-2 30.12, C-3 71.30, C-4 36.44, C-5 48.68, C-6 73.13, C-7 34.45, C-8 30.96, C-9 34.06, C-10 33.97, C-11 28.51, C-2 73.13, C-13 46.63, C-14 48.00, C-15 23.70, C-16 27.51, C-17 47.41, C-18 12.86, C-19 25.41, C-20 35.16, C-21 17.43, C-22 31.17, C-23 30.96, C-24 174.78, C-25 51.59(Ref. 0030)

MASS SPECTRA:Me ester (70eV) m/z: 404(M-H2O, 4%), 386(M-2H2O, 28%), 368(M-3H2O, 12%), 289(M-H2O-SC, 19%), 271(M-2H2O-SC, 100%), 253(M-3H2O-SC, 34%)(Ref. 0030)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Identified in urine of healthy humans and patients with liver diseases.(Ref. 0143/0150/0151)
Constituent of a urinary bile acid in late prenancy 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
[0030]
AUTHOR:Iida, T., Tamaru, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. XVIII. Synthesis of stereoisomeric 3,6,12 alpha-trihydroxy-5 beta-cholanoic acids PubMed ID:1856610
JOURNAL:J Lipid Res.
VOL:32 PAGE : 649-658 (1991)
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[0143]
AUTHOR:Alme, B., Norden, A., and Sjovall, J.
TITLE:Glucuronides of unconjugated 6-hydroxylated bile acids in urine of a patient with malabsorption PubMed ID:668117
JOURNAL:Clin Chim Acta.
VOL:86 PAGE : 251-259 (1978)
[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)
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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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[0216]
AUTHOR:Ratliff, R. L., Matschiner, J. T., Doisy, E. A., Jr., Hsia, S. L., Thayer, S. A., Elliott, W. H., and Doisy, E. A.
TITLE:Bile acids. XV. Partial synthesis of the new metabolite of deoxycholic acid, 3 alpha,6 beta,12 alpha-trihydroxycholanic acid PubMed ID:13739746
JOURNAL:J Biol Chem.
VOL:236 PAGE : 685-687 (1961)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.