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Bile acid


DATA No : BBA0103 INFORMANT : Takashi Iida

NAME : (23S)-3a,7a,23-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:215degC(Ref. 0053)
197-199degC (Me ester)(Ref. 0052)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20: +15deg (C=1.0, EtOH)(Ref. 0053)
[a]d-23: +20deg (C=0.5, CHCl3) (Me ester)(Ref. 0052)
M/D: +84deg (Me ester)(Ref. 0052)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmax cm-1: 1730 (C=O), 3500 (OH)(Ref. 0053)

NMR SPECTRA:Me ester 1H-NMR(CDCl3+CD3OD) d: 18-Me 0.69(s), 19-Me 0.91(s), 21-Me 1.01(d), 3b-H 3.38(m), COOMe 3.76(s), 3timesOH 4.00(s), 23-H 4.24(m)(Ref. 0053/0054)
Me ester 13C-NMR(CDCl3+CD3OD) d: C-20 33.60, C-21 19.50, C-22 41.40, C-23 69.90, C-24 176.20, C-25 52.30(Ref. 0053)

MASS SPECTRA:Me ester (15eV) m/z: 422(M+, 10.8%), 404(M-18, 45.0%), 386(M-2x18, 100%), 371(M-15-2x18, 31.2%), 332(M-18-ring A, 8.5%), 315(M-18-C23-C24, 12.2%), 297(M-2x18-C23-C24, 21.8%), 273(M-18-SC, 27.7%), 264(M-SC-C16-C17, 33.1%), 255(M-2x18-SC, 35.9%), 246(M-18-SC-C16-C17, 26.1%), 228(M-2x18-SC-C16-C17, 34.0%), 213([M-15-2x18-SC-C16-C17, 21.1%), 201(M-18-ring A-SC, 9.5%)(Ref. 0052)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Primary bile acid in bony fish.(Ref. 0102)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0052]
AUTHOR:Kutner, A., and Jaworska, R.
TITLE:Synthesis and absolute configuration at C-23 of [23R and 23S]-3 alpha, 7 alpha, 23-trihydroxy-5 beta-cholan-24-oic and [23R and 23S]-3 alpha, 7 alpha, 12 alpha, 23-tetrahydroxy-5 beta-cholan-24-oic acids PubMed ID:7157443
JOURNAL:Steroids.
VOL:40 PAGE : 11-22 (1982)
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[0053]
AUTHOR:Pellicciari, R., Natalini, B., Roda, A., Machado, M. I. L., and Marinozzi, M.
TITLE:Preparation and Physicochemical Properties of Natural (23R)-3a,7a,23- and (23R)-3a,12a,23- Trihydroxylated Bile Acids and Their (23S)- Epimers.
JOURNAL:J. Chem. Soc. Perkin. Trans. I.
VOL: PAGE : 1289 -1296 (1989)
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[0054]
AUTHOR:Klinot, J., Jirsa, M., Klinotova, E., Ubik, K., and Protiva, J.
TITLE:Isolation of (23R) 3a,7a,23-Trihydroxy-5b-cholan-24-oic (b-Phocaecholic) Acid from Duck Bile. 1H NMR Spectra of Its Derivatiues
JOURNAL:Collect. Czecho. Chem. Commun.
VOL:51 PAGE : 1722 -1730 (1986)
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[0102]
AUTHOR:Hofmann, A. F., Schteingart, C. D., and Hagey, L. R. (1995) Species Differences in Bile Acid Metabolism, in Bile Acids in Liver Diseases (Paumgartner, G., and Beuers, U. eds), pp 3-30, Kluwer Academic Publishers, Dordrecht.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.