Back to HOME

Bile acid


DATA No : BBA0049 INFORMANT : Takashi Iida

NAME : 7a,12a-Dihydroxy-5b-cholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O4 MOL.WT (average) : 392.572


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:204-206degC, (Me ester; mp, 155-156degC)(Ref. 0027)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-21: +81deg (dioxane), [a]d-21: +17deg (CHCl3) (Me ester)(Ref. 0001)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:nmaxmm: 9.68, 9.72, 10.20, 10.53(Ref. 0003)
Me ester: nmax cm-1: 1724 (C=O), 3425, 1024, 984 (OH)(Ref. 0026)

NMR SPECTRA:Me ester 1H-NMR (CDCl3; 100MHz) d: 18-Me 0.68(s), 19-Me 0.89(s), COOMe 3.63(s), 7b- 3.84(m), 12b-H 3.96(m)(Ref. 0026)
13C-NMR (CDCl3; 22.53MHz) d: C-1 37.5, C-2 21.2, C-3 27.7, C-4 30.4, C-5 43.1, C-6 35.4, C-7 68.7, C-8 39.5, C-9 26.3, C-10 35.6, C-11 28.1, C-12 73.1, C-13 46.5, C-14 41.5, C-15 23.2, C-16 27.4, C-17 47.1, C-18 12.4, C-19 23.2, C-20 35.3, C-21 17.2, C-22 31.1, C-23 30.8, C-24 174.6, C-25 51.3(Ref. 0006)

MASS SPECTRA:m/z: 374(M-H2O, 3.2%), 356(M-2H2O, 72.5%), 273(M-H2O-SC, 8.8%), 255(M-2H2O-SC, 100.0%)(Ref. 0027)
Me ester (70eV) m/z: 370(M-2H2O,36%), 355(M-2H2O-CH3, 11%), 255(M-2H2O-SC, 100%), 228(M-2H2O-SC-part of ring D (27), 11%), 213(M-2H2O-SC-ring D (42), 4%)(Ref. 0010)
Me ester-DMES ether m/z: 578(M+, 0.2%), 563(M-CH3, 3.1%), 549(M-29, 100.0%), 370(M-2DMESOH, 29.7%), 255(M-2DMESOH-SC, 33.7%)(Ref. 0009/0027)
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]

[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)
[TOP]

[0027]
AUTHOR:Arimoto, K., Adachi, K., and Yamaga, N.
TITLE:7 beta,12 beta-Dihydroxy-5 beta-cholan-24-oic acid as an internal standard for quantitative determination of bile acids by gas chromatography PubMed ID:7157435
JOURNAL:Steroids.
VOL:39 PAGE : 631-641 (1982)
[TOP]

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