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Bile acid


DATA No : BBA0136 INFORMANT : Takashi Iida

NAME : 3,7-Dioxo-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H36O4 MOL.WT (average) : 388.540


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:145degC, (Me ester; mp, 152-155degC)(Ref. 0067)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D: -36deg (C=0.2, CHCl3)(Ref. 0067)
[a]D: -27deg (CH3COCH3)(Ref. 0002)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax m: 9.6-9.7, 9.91(Ref. 0003)
Me ester: nmaxcm-1: 1740 (COOMe), 1715 (C=O)(Ref. 0067)

NMR SPECTRA:Me ester 1H-NMR (CDCl3) d: 0.70 (3H, s, 18-CH3), 1.31 (3H, s, 19-CH3), 0.92 (3H, d, J=5Hz, 21-CH3), 3.7(3H, s, COOMe)(Ref. 0005/0067)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 35.4, C-2 36.6, C-3 210.7, C-4 42.9, C-5 47.7, C-6 44.9, C-7 209.7, C8 49.5, C-9 42.9, C-10 35.4, C-11 22.1, C-12 38.9, C-13 42.9, C-14 48.9, C-15 24.7, C-16 28.1, C-17 54.8, C-18 12.0, C-19 22.3, C-20 35.1, C-21 18.3, C-22 31.0, C-23 31.0, C-24 174.3, C-25 51.3(Ref. 0004/0064/0140)

MASS SPECTRA:Me ester (70eV) m/z: 402(M+, 62%), 387(M-CH3, 4%), 384(M-H2O, 6%), 370(M-32, 28%), 353(M-H2O-31, 26%), 329(M-73, 33%), 287(M-SC, 100%), 269(M-H2O-SC, 40%), 261(M-SC-26, 5%), 260(M-SC-27, 11%), 251(M-2H2O-SC, 4%), 247(M-SC-40, 9%), 246(M-SC-41, 10%), 245(M-SC-42, 14%)(Ref. 0009)
The spectrum (70eV) was shown as the Me ester derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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 : - ()
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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]

[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 : - ()
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[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]

[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.
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JOURNAL:
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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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[0064]
AUTHOR:Iida, T., Tamura, T., Matsumoto, T., and Chang, F. C.
TITLE:Carbon-13 NMR Spectra of Oxobile Acid Methyl Esters.
JOURNAL:J. Jpn. Oil Chem. Soc. (Yukagaku)
VOL:32 PAGE : 232 -233 (1983)
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[0067]
AUTHOR:Mappus, E., and Cuilleron, C. Y.
TITLE:Synthesis and stereochemistry of C-3- and C-7-linked (O-carboxymethyl)-oximino- and hemisuccinamido derivatives of 5 alpha-dihydrotestosterone PubMed ID:462506
JOURNAL:Steroids.
VOL:33 PAGE : 693-718 (1979)
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[0140]
AUTHOR:Lappalainen, K., Kolehmainen, E., Kaartinen, M., Kauppinen, R., Seppälä, R., and Vatanen, V.
TITLE:Substituted Methyl 5b-Cholan-24-oates. II. 13C NMR Spectral Assignment.
JOURNAL:Magn. Reson. Chem.
VOL:32 PAGE : 786 -788 (1994)
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