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Bile acid


DATA No : BBA0079 INFORMANT : Takashi Iida

NAME : 3a,5b,12a-Trihydroxycholan-24-oic Acid

COMMON NAME:
SYMBOL:
FORMULA: C24H40O5 MOL.WT (average) : 408.571


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:127-128degC (Me ester-3,12-diacetate)(Ref. 0226)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-22: +77.3deg (C=1.0, CHCl3) (Me ester-3,12-diacetate)(Ref. 0048)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Me ester-3,12-diacetate: nmax cm-1 (CHCl3): 3617, 1728, 1712, 1699(Ref. 0048)

NMR SPECTRA:Me ester-3,12-diacetate 1H-NMR d: 18-Me 0.69(s), 21-Me 0.77(d, J=6.1Hz), 19-Me 0.84(s), 3a-OCOMe 1.99(s), 12a-OCOMe 2.07(s), COOMe 3.63(s), 3b-H 5.03(tt, J, 11.1, 4.7), 12b-H 5.07(m)(Ref. 0048/0226)
Me ester-3,12-diacetate13C-NMR (CDCl3; 125MHz) d: C-1 28.96, C-2 26.01, C-3 71.19, C-4 37.92, C-5 74.80, C-6 36.36, C-7 28.02, C-8 34.50, C-9 36.96, C-10 38.87, C-11 27.11, C-12 75.44, C-13 44.67, C-14 49.28, C-15 23.25, C-16 25.79, C-17 47.29, C-18 12.19, C-19 15.87, C-20 34.64, C-21 17.31, C-22 30.79, C-23 30.64, C-24 174.56, Acetyl Me 21.27,21.15, C=O 170.37, OCH3 51.35(Ref. 0048/0228)

MASS SPECTRA:Me ester-3,12-diacetate m/z: 428(29%), 386(21%), 368(84%), 353(24%), 332(55%), 331(53%), 313(40%), 271(44%), 253(100%), 211(24%)(Ref. 0048/0228)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0048]
AUTHOR:Dixon, J. T., Holzafel, C. W., and Heerden, F. R.
TITLE:Selective Oxidation of Unactivated 5b C-H Bonds in Steroids by Dimethyldioxirane.
JOURNAL:Synth. Commun.
VOL:23 PAGE : 135 -141 (1993)
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[0226]
AUTHOR:Bovicelli, P., Gambacorta, A., Lupattelli, P., and Mincione, E.
TITLE:A Highly Regio- and Stereoselevtic C5 Oxyfunctionalization of Coprostane Steroids by Dioxirnes: an Improved Access to Progestogen and Androgen Hormones.
JOURNAL:Tetrahedron lett.
VOL:33 PAGE : 7411 -7412 (1992)
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[0228]
AUTHOR:Cerr$`e$, C., Hofmann, A. F., and Schteingart, C. D.
TITLE:Oxyfunctionalization of (5b)-Bile Acids by Dimethyldioxrane: Hydroxylation at C-5, C-14, and C-17.
JOURNAL:Tetrahedron
VOL:53 PAGE : 435 -446 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.