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Bile acid


DATA No : BBA0068 INFORMANT : Takashi Iida

NAME : 3b,6a,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:214-217degC(Ref. 0029)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: +5deg (MeOH)(Ref. 0073)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 1708(C=O), 3440, 1048(OH)(Ref. 0029)

NMR SPECTRA:1H-NMR (CDCl3+10%DMSO-d6; 90MHz) d: 18-Me 0.66(s), 21-Me 0.92(d), 19-Me 0.94(s), 7b-H 3.84(m), 6b-H 3.90(brm), 3a-H 4.08(m)(Ref. 0029/0073)
Me ester 1H-NMR (CDCl3; 500MHz) d: 18-Me 0.69(s), 19-Me 0.94(s), 21-Me 0.93(d), COOMe 3.66(s), 7b-H 3.86(m), 6h-H 3.95(m), 3a-H 4.12(m)(Ref. 0029)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 30.0, C-2 27.4, C-3 66.0, C-4 29.3, C-5 42.4, C-6 71.8, C-7 69.5, C-8 38.4, C-9 32.0, C-10 36.4, C-11 20.9, C-12 39.4, C-13 42.7, C-14 50.2, C-15 23.4, C-16 28.0, C-17 55.7, C-18 11.6, C-19 23.6, C-20 35.3, C-21 18.2, C-22 30.9, C-23 30.9, C-24 174.6, C-25 51.4(Ref. 0029)

MASS SPECTRA:Me ester (70eV) m/z: 422 (M+, 7%), 404(M-H2O, 34%), 386(M-2H2O, 57%), 371(M-2H2O-CH3, 11%)(Ref. 0029)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0029]
AUTHOR:Iida, T., Momose, T., Tamura, T., Matsumoto, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers PubMed ID:2769078
JOURNAL:J Lipid Res.
VOL:30 PAGE : 1267-1279 (1989)
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[0073]
AUTHOR:Riva, S., Bovara, R., Zetta, L., Pasta, P., Ottolina, G., and Carrea, G.
TITLE:Enzymatic a/b Inversion of C-3 Hydroxyl of Bile Acids and Study of the Effects of Organic Solvents on Reaction Rates.
JOURNAL:J. Org. Chem.
VOL:53 PAGE : 88 -92 (1988)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.