Back to HOME

Bile acid


DATA No : BBA0001 INFORMANT : Takashi Iida

NAME : 5b-Cholan-24-oic Acid

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


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:164degC, (Me ester; mp, 86degC)(Ref. 0001/0002)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]14D: +21.74deg (CHCl3)(Ref. 0001/0002)
[a]D: +23.2deg (dioxane) (Me ester)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxm: 9.68, 10.58(Ref. 0003)
Me ester: nmaxm: 9.65, 9.88, 10.60(Ref. 0003)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.64(s), 21-Me 0.90(d), 19-Me 0.91(s)(Ref. 0004/0005)
Me ester 13C-NMR(CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.2, C-3 26.9, C-4 27.4, C-5 43.6, C-6 27.1, C-7 26.4, C-8 35.7, C-9 40.4, C-10 35.2, C-11 20.7, C-12 40.2, C-13 42.6, C-14 56.5, C-15 24.1, C-16 28.0, C-17 55.8, C-18 11.9, C-19 24.1, C-20 35.2, C-21 18.1, C-22 30.8, C-23 30.8, C-24 174.2, C-25 51.1(Ref. 0004/0006)

MASS SPECTRA:Me ester (22eV) m/z: 374(M+), 359(M-CH3, 100%), 343(M-CH3O, 2%), 325(M-CH3O-H2O, 5%), 317(4%), 278(M-ring A, 5%), 264(M-ring A and C-6, 12%), 259(M-SC, 1%), 257(M-SC-2H, 1%), 249(M-ring A and C-6-CH3, 1%), 232(ABC ion, 15%), 217(ABC-ring ion, 100%), 203(11%)(Ref. 0039)
The spectrum (70eV) was shown as the Me-ester derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolated from the embryo of the jequirity bean, Abrus precatorius.(Ref. 0001)
Detected as a trace component of human feces.(Ref. 0101)
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 : - ()
[TOP]

[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:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0003]
AUTHOR:Levin, S. J., and Johnston, C. G.
TITLE:Infrared Correlations in the Bile Acid Series
JOURNAL:Talanta.
VOL:8 PAGE : 871 -879 (1961)
[TOP]

[0004]
AUTHOR:Barnes, S., and Kirk, D. N. (1988) Nuclear Magnetic Resonance Spectroscopy of Bile Acids, in The Bile Acids-Chemistry, Physiology, and Metabolism (Vol. 4: Methods and Applications) (Setchell, K. D. R., Kritchevsky, D., and Nair, P. P. eds), pp65-136, Plenum Press, New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0005]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Proton Nuclear Magnetic Resonance Spectra of Hydroxylated Bile Acid Isomers and Their Oxo Derivatives
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:24 PAGE : 163 -165 (1983)
[TOP]

[0006]
AUTHOR:Iida, T., Tamura, T.,Matsumoto, T., Chang, F. C.
TITLE:Carbon-13 NMR Spectra of Hydroxylated Bile Acid Stereoisomers.
JOURNAL:Org. Magn. Reson.
VOL:21 PAGE : 305 -309 (1983)
[TOP]

[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:
VOL: PAGE : - ()
[TOP]

[0039]
AUTHOR:Lee, S. P., Lester, R., and Pyrek, J. S.
TITLE:Vulpecholic acid (1 alpha, 3 alpha, 7 alpha-trihydroxy-5 beta-cholan-24-oic acid): a novel bile acid of a marsupial, Trichosurus vulpecula (Lesson) PubMed ID:3559398
JOURNAL:J Lipid Res.
VOL:28 PAGE : 19-31 (1987)
[TOP]

[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 : - ()
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.