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Bile acid


DATA No : BBA0015 INFORMANT : Takashi Iida

NAME : 12a-Hydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O3 MOL.WT (average) : 376.573


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:110-116degC(Ref. 0001)
120.7-122.7degC (Me ester)(Ref. 0040)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-12: +37.9deg (C=1.844, acetone)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxm: 9.65, 9.91, 10.6-10.7(Ref. 0003)
Me ester: nmaxcm-1: 1715 (C=O), 3559 (OH), 1205, 1174(Ref. 0040)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.68(s), 19-Me 0.93(s), 21-Me 0.96(d), 12b-H 3.91(m)(Ref. 0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.2, C-2 21.0, C-3 26.7, C-4 27.2, C-5 43.5, C-6 26.9, C-7 26.0, C-8 35.8, C-9 33.4, C-10 34.6, C-11 28.5, C-12 72.8, C-13 46.2, C-14 48.0, C-15 23.5, C-16 27.2, C-17 49.6, C-18 12.5, C-19 23.7, C-20 34.9, C-21 16.9, C-22 30.7, C-23 30.7, C-24 174.2, C-25 51.1(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 372(M-H2O, 7%), 257(M-H2O-SC, 100%), 215(M-H2O-SC-ring D (42), 7%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

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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[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]

[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 : - ()
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[0009]
AUTHOR:Elliott, W. H. (1972) Bile Acids, in Biochemical Applications of Mass Spectrometry (Waller, G. R. ed), pp291-312, John Wiley & Sons, Inc. New York.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0010]
AUTHOR:Iida, T., Chang, F. C., Matsumoto, T., and Tamura, T.
TITLE:High Resolution Mass Spectra of Mono-, Di- and Trihydroxy Stereoisomers of Bile Acids.
JOURNAL:Biomed. Mass Spectrom.
VOL:9 PAGE : 473 -476 (1982)
[TOP]

[0040]
AUTHOR:Baker, J. F., and Blickenstaff, R. T.
TITLE:Intramolecular catalysis. VIII. Effects on the acetylation of the 7alpha-hydroxyl group of steroids. A H nuclear magnetic resonance rate method PubMed ID:1142040
JOURNAL:J Org Chem.
VOL:40 PAGE : 1579-1586 (1975)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.