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Bile acid


DATA No : BBA0011 INFORMANT : Takashi Iida

NAME : 7a-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:96-99degC(Ref. 0001)
80-81degC (Me ester)(Ref. 0040)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-22: +7deg (CHCl3)(Ref. 0001)
[a]d-20: +6pm2deg (C=1.5) (Me ester)(Ref. 0132)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxm: 9.70, 9.91, 10.22, 10.59(Ref. 0003)
Me ester: nmaxcm-1: 1724 (C=O), 3584 (OH), 1106(Ref. 0040)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 90MHz) d: 18-Me 0.65(s), 19-Me 0.91(s), COOMe 3.68(s), 7b-H 3.86(br)(Ref. 0040)
Me ester 13C-NMR (CDCl3; 22.53MHz) d: C-1 37.4, C-2 21.1, C-3 27.5, C-4 30.2, C-5 43.7, C-6 35.5, C-7 68.1, C-8 39.2, C-9 32.6, C-10 35.0, C-11 20.3, C-12 39.4, C-13 42.3, C-14 50.1, C-15 23.3, C-16 27.8, C-17 55.5, C-18 11.4, C-19 23.3, C-20 35.0, C-21 17.9, C-22 30.6, C-23 30.6, C-24 174.1, C-25 51.0(Ref. 0006)

MASS SPECTRA:Me ester (70eV) m/z: 372(M-H2O, 100%), 358(M-MeOH, 10%), 357(M-H2O-CH3, 40%), 276(M-114, 16%), 257(M-H2O-SC, 70%), 230(M-H2O-SC-part of ring D (27), 31%), 217(M-173, 13%), 215(M-H2O-SC-ring D (42), 61%)(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 : - ()
[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]

[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 : - ()
[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]

[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)
[TOP]

[0132]
AUTHOR:Kagan, H. B., and Jacques, J.
TITLE:Acides Biliaires Comportant des Hydroxyles en Position 6 et 7.
JOURNAL:Bull. Soc. Chim. Fr.
VOL: PAGE : 871 -878 (1960)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.