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Bile acid


DATA No : BBA0061 INFORMANT : Takashi Iida

NAME : 3b,4b,7a-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:212-214degC, (Me ester; mp, 203-205degC)(Ref. 0017)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1712(C=O), 3372(OH)(Ref. 0017)

NMR SPECTRA:1H-NMR (CDCl3+20%DMSO-d6; 90MHz) d: 18-Me 0.65(s), 21-Me 0.92(d), 19-Me 0.94(s), 3a- and 7b-H 3.87(m), 4a-H 4.33(brm)(Ref. 0017)
Me ester 1H-NMR (CDCl3; 500MHz ) d: 18-Me 0.64(s), 19-Me 0.94(s), 21-Me 0.90(d), COOMe 3.64(s), 7b-H 3.88(m), 3a-H 3.95(m), 4a-H 4.35(dd, J, 11.1, 3.4)(Ref. 0017)
13C-NMR (CDCl3; 22.53MHz) d: C-1 29.2, C-2 25.9, C-3 69.5, C-4 71.4, C-5 42.9, C-6 28.0, C-7 68.6, C-8 39.3, C-9 34.0, C-10 36.9, C-11 20.9, C-12 39.6, C-13 42.7, C-14 50.4, C-15 23.6, C-16 28.1, C-17 55.8, C-18 11.8, C-19 22.9, C-20 35.3, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.6, C-25 51.3(Ref. 0017)

MASS SPECTRA:Me ester (60eV) m/z: 404(M-H2O, 100%), 386(M-2H2O, 39%), 368(M-3H2O, 7%), 289(M-H2O-SC, 19%), 271(M-2H2O-SC, 11%), 253(M-3H2O-SC, 5%), 244(M-2H2O-SC-part of ring D (27), 8%), 247(M-H2O-SC-ring D (42), 7%), 229(M-2H2O-SC-42, 14%), 127(75%)(Ref. 0017)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Excreted in urine of healthy premature and full-term infants.(Ref. 0202)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0017]
AUTHOR:Iida, T., Momose, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. XV. Synthesis of 4 beta-hydroxylated bile acids; unique bile acids in human fetal bile PubMed ID:2632079
JOURNAL:Chem Pharm Bull (Tokyo).
VOL:37 PAGE : 3323-3329 (1989)
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[0202]
AUTHOR:Strandvik, B., Wahlen, E., and Wikstrom, S. A.
TITLE:The urinary bile acid excretion in healthy premature and full-term infants during the neonatal period PubMed ID:8171265
JOURNAL:Scand J Clin Lab Invest.
VOL:54 PAGE : 1-10 (1994)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.