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Bile acid


DATA No : BBA0002 INFORMANT : Takashi Iida

NAME : 5a-Cholan-24-oic Acid

COMMON NAME: Allocholanic Acid
SYMBOL:
FORMULA: C24H40O2 MOL.WT (average) : 360.573


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:170degC, (Me ester; mp, 91degC)(Ref. 0001/0002/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]14D: +21.74deg (CHCl3)(Ref. 0001/0002/0237)
[a]D: +22.1deg (Me ester)(Ref. 0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 19-Me 0.77(s), 21-Me 0.90(d)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d : C-1 38.6, C-2 22.1, C-3 26.7, C-4 29.0, C-5 46.9, C-6 29.0, C-7 32.0, C-8 35.4, C-9 54.7, C-10 36.1, C-11 20.7, C-12 40.0, C-13 42.5, C-14 56.5, C-15 24.0, C-16 28.0, C-17 55.8, C-18 11.9, C-19 12.1, C-20 35.2, C-21 18.1, C-22 30.9, C-23 30.9, C-24 174.4, C-25 51.2(Ref. 0011)

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

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected in the biliary bile from alligator mississippiensis.(Ref. 0209)
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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[0002]
AUTHOR:Brooks, C. J. W. (1970) Bile Acids (Chapter 15: Steroids; Sterols and Bile Acids), in Rodd's Chemistry of Carbon Compounds (Vol. II, Part D) (Coffey, S. ed), pp 168-196, Elsevier Publishing Co., Amsterdam.
TITLE:
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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:
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[0008]
AUTHOR:Iida, T., and Shinohara, T.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part2. Mono-, Di- and Trisubstituted Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:28 PAGE : 175 -179 (1987)
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[0011]
AUTHOR:Iida, T., Chang, F. C., Goto, J., and Nambara, T.
TITLE:Carbon-13 Nuclear Magnetic Resonance Spectra of Bile Acid Derivatives. Part II. Mono-, Di- and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:Chem. Phys. Lipids
VOL:45 PAGE : 1 -12 (1987)
[TOP]

[0209]
AUTHOR:Tint, G. S., Dayal, B., Batta, A. K., Shefer, S., Joanen, T., McNease, L., and Salen, G.
TITLE:Biliary Bile Acids, Bile Alchols, and Sterols of Alligator mississippiensis. PubMed ID:7354247
JOURNAL:J. Lipid Res.
VOL:21 PAGE : 110 -117 (1980)
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[0237]
AUTHOR:Elliott, W. H. (1971) Allo Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 1: Chemistry) (Nair, P. P., and Kritchevsky, D. eds), pp47-93, Plenum Press, New York.
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.