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Bile acid


DATA No : BBA0102 INFORMANT : Takashi Iida

NAME : (23R)-3a,7a,23-Trihydroxy-5b-cholan-24-oic Acid

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:225degC(Ref. 0053)
110-112degC (Me ester)(Ref. 0052)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20: +21deg (C=1.06, EtOH)(Ref. 0053)
[a]d-23: +8deg (Me ester)(Ref. 0052)
M/D: +34deg (Me ester)(Ref. 0052)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmax cm-1: 1730 (C=O), 3500 (OH)(Ref. 0053/0054)

NMR SPECTRA:1H-NMR(CDCl3+DMSO-d6; 80MHz) d: 18-Me 0.69(s), 19-Me 0.98(s), 21-Me 0.97(d), 23-H 4.03(dd, J, 10.5 2.0)(Ref. 0054)
Me ester 1H-NMR(CDCl3+CD3OD) d: 18-Me 0.69(s), 19-Me 0.90(s), 21-Me 1.01(d), 3b-H 3.38(m), COOMe 3.78(s), 3timesOH 3.98(s), 23-H 4.24(m)(Ref. 0053/0054)
Me ester 13C-NMR(CDCl3+CD3OD) d: C20 32.30, C21 17.97, C22 41.50, C23 68.40, C24 176.50, C25 52.30(Ref. 0053)

MASS SPECTRA:Me ester (15eV) m/z: 422(M+, 7.6%), 404(M-18, 41.6%), 386 (M-2x18, 100%), 371(M-15-2x18, 40.1%), 332(M-18-ring A, 11.3%), 315(M-18-C23-C24, 13.0%), 297(M-2x18-C23-C24, 23.3%), 273(M-18-SC, 25.0%), 264(M-SC-C16-C17, 31.5%), 255(M-2x18-SC, 40.5%), 246(M-18-SC-C16-C17, 30.5%), 228(M-2x18-SC-C16-C17, 42.5%), 213(M-15-2x18-SC-C16-C17, 24.9%), 201(M-18-ring A-SC, 12.1%)(Ref. 0052)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from seal and walrus bile.(Ref. 0001/0101)
Isolated from duck bile.(Ref. 0054)
Primary bile acid in marine manmals and wading birds.(Ref. 0102)
Isolated from the biliary biles of flamingos and ducks.(Ref. 0165)
Isolated from the leopard seal, Hydrurga leptonyx, and the California sealion, Zalophus californianus.(Ref. 0168)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Hill, R. A., Kirk, D. N., Makin, H. L. J., and Murphy, G. M. (1991) Chemical Data, Structures and Bibliographies, in Dictionary of Steroids, Chapman & Hall, London.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[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)
[TOP]

[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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[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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[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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[0165]
AUTHOR:Hagey, L. R., Schteingart, C. G., Ton-Nu, H-T., Rossi, S. S., Odell, D., and Hofmann, A. F.
TITLE:b-Phocacholic Acid in Bile; Biochemical Evidence that the Flamingo is Related to an Ancient Goose.
JOURNAL:The Condor.
VOL:92 PAGE : 593 -597 (1990)
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[0168]
AUTHOR:Haslewood, G. A.
TITLE:Comparative studies of 'bile salts'. 13. Bile acids of the leopard seal, Hydrurga leptonyx, and of two snakes of the genus Bitis PubMed ID:13712142
JOURNAL:Biochem J.
VOL:78 PAGE : 352-359 (1961)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.