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Bile acid


DATA No : BBA0013 INFORMANT : Takashi Iida

NAME : 7a-Hydroxy-5a-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:155-156degC, (Me ester; mp, 105-106degC)(Ref. 0038/0237)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25: -1.0pm0.5deg (C=1.0, MeOH)(Ref. 0038/0237)
[a]d-25: +2deg (C=0.95, MeOH) (Me ester)(Ref. 0001/0237)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax cm-1: 3279, 1701, 1255, 1236, 1212, 1096, 1029, 1014, 993, 959, 888, 778(Ref. 0038)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.66(s), 19-Me 0.78(s), 21-Me 0.92(d), 7b-H 3.80(m)(Ref. 0008)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 38.6, C-2 22.2, C-3 26.8, C-4 28.8, C-5 39.4, C-6 37.1, C-7 68.1, C-8 39.8, C-9 46.6, C-10 36.5, C-11 20.8, C-12 39.9, C-13 42.9, C-14 50.9, C-15 23.7, C-16 28.0, C-17 56.2, C-18 11.9, C-19 11.1, C-20 35.4, C-21 18.4, C-22 31.2, C-23 31.2, C-24 174.2, C-25 51.0(Ref. 0011)

MASS SPECTRA:Me ester (20eV) m/z: 390(M+1, 7%), 372(M-H2O, 100%), 357(M-H2O-CH3, 22%), 257(M-H2O-SC, 76%), 249(M-141, 11%), 248(M-SC-part of ring D (27), 28%), 233(M-SC-ring D (42), 30%), 230(M-H2O-SC-27, 69%), 217(M-173, 24%), 215(M-H2O-SC-42, 31%)(Ref. 0009/0012)

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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[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)
[TOP]

[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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[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]

[0012]
AUTHOR:Iida, T., Tamura, T., and Matsumoto, T.
TITLE:Mass Spectra of Mono-, Di-, and Trihydroxy Stereoisomers of Methyl 5a-Cholanoates.
JOURNAL:J. Coll. Engin. Nihon Univ. (A)
VOL:29 PAGE : 279 -288 (1988)
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[0038]
AUTHOR:Mitra, M. N., and Elliott, W. H.
TITLE:Bile acids. 23. A new direct synthesis of allocholic acid and its 3 beta isomer PubMed ID:5634890
JOURNAL:J Org Chem.
VOL:33 PAGE : 175-181 (1968)
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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.
TITLE:
JOURNAL:
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.