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Bile acid


DATA No : BBA0138 INFORMANT : Takashi Iida

NAME : 3,12-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:179-181deg(Ref. 0068)
133-134deg (Me ester)(Ref. 0001)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-23: +94.8deg (C=0.6, dioxane)(Ref. 0068)
[a]D: +88.5deg (C=2.2, CHCl3) (Me ester)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmax m: 9.6-9.7, 10.53(Ref. 0003)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 21-Me 0.85(d), 18-Me 1.06(s), 19-Me 1.11(s)(Ref. 0004/0005)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 36.8, C-2 36.8, C-3 211.6, C-4 42.0, C-5 43.7, C-6 25.5, C-7 26.6, C-8 35.4, C-9 44.3, C-10 35.6, C-11 38.3, C-12 213.7, C-13 57.5, C-14 58.5, C-15 24.2, C-16 27.4, C-17 46.5, C-18 11.7, C-19 22.1, C-20 35.6, C-21 18.5, C-22 31.3, C-23 30.5, C-24 174.4, C-25 51.3(Ref. 0004/0064/0140)

MASS SPECTRA:Me ester (70eV) m/z: 402(M+, 100%), 387(M-CH3, 3%), 384(M-H2O, 8%), 370(M-32, 7%), 353(M-H2O-31, 2%), 329(M-73, 18%), 287(M-SC, 15%), 269(M-H2O-SC, 12%), 261(M-SC-26, 5%), 260(M-SC-part of ring D (27), 9%), 251(M-2H2O-SC, 7%), 247(M-SC-40, 86%), 246(M-SC-41, 2%), 245(M-SC-ring D (42), 12%)(Ref. 0009)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected in human feces.(Ref. 0101/0161/0205)
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]

[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]

[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]

[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 : - ()
[TOP]

[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)
[TOP]

[0068]
AUTHOR:Mickova, R.
TITLE:Preparation of Pregnane Derivatives from Bile Acids.
JOURNAL:Collect. Czecho. Chem. Commun.
VOL:49 PAGE : 1617 -1621 (1983)
[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]

[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)
[TOP]

[0161]
AUTHOR:Eneroth, P., Gordon, B., Ryhage, R., and Sjovall, J.
TITLE:Identification of mono- and dihydroxy bile acids in human feces by gas-liquid chromatography and mass spectrometry PubMed ID:5966634
JOURNAL:J Lipid Res.
VOL:7 PAGE : 511-523 (1966)
[TOP]

[0205]
AUTHOR:Tandon, R., Axelson, M., and Sjovall, J.
TITLE:Selective liquid chromatographic isolation and gas chromatographic-mass spectrometric analysis of ketonic bile acids in faeces PubMed ID:6501503
JOURNAL:J Chromatogr.
VOL:302 PAGE : 1-14 (1984)
[TOP]

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