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Bile acid


DATA No : BBA0113 INFORMANT : Takashi Iida

NAME : (23R)-3a,12a,23-Trihydroxy-5b-cholan-24-oic Acid

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


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:230-232degC, (Me ester: mp, 119-120degC)(Ref. 0053)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20: +48deg (C=0.856, EtOH), [a]d-20: +44.2deg (C=0.34, EtOH) (Me ester)(Ref. 0053)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

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

NMR SPECTRA:Me ester 1H-NMR (CDCl3+CD3OD) d: 18-Me 0.71(s), 19-Me 0.91(s), 21-Me 1.10(d), 3b-H and 3timesOH 3.45(m), COOMe 3.81(s), 12b-H 4.05(m), 23-H 4.28(m)(Ref. 0053)
Me ester 13C-NMR (CDCl3+CD3OD) d: C-20 32.37, C-21 17.08, C-22 40.88, C-23 68.43, C-24 176.69, C-25 52.36(Ref. 0053)

MASS SPECTRA:The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from the bile of certain snakes, especially of the Gaboon viper, Bitis gabonica Viperidae and puff adder, Bitis arietans.(Ref. 0001/0101/0168)
Isolated from snake bile ; identified in the European adder Vipera kerus ; stereochemistry of a hydroxyl group at C-23 is unidentified.(Ref. 0100)
A bacterial 7-dehydroxylation product of (23R)-3a,7a,12a,23+tetrahydroxy-5b-cholan-24-oic acid.(Ref. 0102)
Isolated from snakes of the subfamily Viperinae ; A biotransformation product of deoxycholic acid in the adder (Vipera berus; Linn.) liver.(Ref. 0175)
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:
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[0007]
AUTHOR:Lawson, A. M., and Setchell, K. D. R. (1988) Mass Spectrometry of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchall, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp 167-267, Plenum Press, New York.
TITLE:
JOURNAL:
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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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[0100]
AUTHOR:Haselwood, G. A. D. (1978) The Biological Importance of Bile Salts, in Frontiers of Biology (Vol. 47) (Neuberger, A., and Tatum, E. L. eds), North-Holland Publishing Co., Amsterdam.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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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:
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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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[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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[0175]
AUTHOR:Ikawa, S., and Tammar, A. R.
TITLE:Bile acids of snakes of the subfamily Viperinae and the biosynthesis of C-23-hydroxylated bile acids in liver homogenate fractions from the adder, Vipera berus (Linn.) PubMed ID:6007
JOURNAL:Biochem J.
VOL:153 PAGE : 343-350 (1976)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.