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Bile acid


DATA No : BBA0012 INFORMANT : Takashi Iida

NAME : 7b-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:131-133.5degC, (Me ester; mp, 89.0-90.5degC)(Ref. 0026)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester: nmaxcm-1: 1695 (C=O), 3401, 1015, 990 (OH)(Ref. 0026)

NMR SPECTRA:1H-NMR (CDCl3; 100MHz) d: 18-Me 0.68(s), 19-Me 0.93(s), 7a-H 3.58(brm)(Ref. 0026)
Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.64(s), 19-Me 0.99(s), 7a-H 3.60(brm), COOMe 3.68(s)(Ref. 0026)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.4, C-2 21.0, C-3 26.7, C-4 28.4, C-5 44.0, C-6 37.1, C-7 71.2, C-8 43.6, C-9 39.1, C-10 34.7, C-11 20.9, C-12 40.1, C-13 43.6, C-14 55.7, C-15 26.9, C-16 27.9, C-17 54.8, C-18 12.0, C-19 24.1, C-20 35.1, C-21 18.2, C-22 30.8, C-23 30.8, C-24 174.3, C-25 51.2(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 390(M+1, 16%), 372(M-H2O, 100%), 358(M-MeOH, 11%), 357(M-H2O-CH3, 34%), 276(M-114, 16%), 257(M-H2O-SC, 64%), 233(M-SC-ring D (42), 15%), 230(M-H2O-SC-part of ring D (27), 33%), 217(M-173, 45%), 215(M-H2O-SC-42, 37%)(Ref. 0009/0010)
The spectrum (70eV) was shown as the Me-TMS derivative(Ref. 0007)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Detected as a trace component of human stool.(Ref. 0101)
Detected in human feces.(Ref. 0219)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[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)
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[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)
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[0026]
AUTHOR:Iida, T., and Chang, F. C.
TITLE:Potential Bile Acid Metabolites. 8. 7,12-Dihydroxy- and 7b-Hydroxy-5b-cholanic Acids.
JOURNAL:J. Org. Chem.
VOL:48 PAGE : 1194 -1197 (1983)
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[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 : - ()
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[0219]
AUTHOR:Hayakawa, S.
TITLE:Intestinal Bacteria and Bile Acids.
JOURNAL:Saishin Igaku.
VOL:37 PAGE : 1920 -1927 (1982)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.