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Steroid


DATA No : SST0206 INFORMANT : Hideaki Nishino

NAME : 5a-Cholestan-3a-ol; 3a-Hydroxycholestane; e-Cholestanol

COMMON NAME: Epicholestanol
SYMBOL:
FORMULA: C27H48O MOL.WT (average) : 388.669


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BIOLOGICAL ACTIVITY
Preparation from cholestanone. (Ref. 0035/0366) Synthesis from cholesterol via a-cholestyl chloride. (Ref. 0794)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:185-186degC (alcohol). (Ref. 0794), 182-184degC. (Ref. 0366)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]20/D=+32.2deg (c=2.0 in chloroform). (Ref. 0366)

DENSITY:

SOLUBILITY:Lower solubility than cholestanol. (Ref. 0794)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
Not ppt with digitonin. Epicholestanyl acetate, m.p. 92-94deg (Ref. 0366)
REFERENCES
[0035]
AUTHOR:Ruzicka,L., Brüngger,H., Eichenberger,E., and Meyer,J.
TITLE:Polyterpene und Polyterpenoide XCI. Zur Präparativen Hersterins und Epi-Dihydro-Cholesterins. Beitrag zur Kenntnis der Räumlichen Lage der Hydroxylgruppe bei den Sterinen.
JOURNAL:Helv.Chim.Acta.
VOL:17 PAGE : 1407 -1416 (1934)
[TOP]

[0366]
AUTHOR:Barnett,J.,Heilbron,I.M.,Jones,E.R.H.,and Verrill,K.J.
TITLE:Studies in the sterol group. Part XLI. A new epimerisation process.
JOURNAL:J. Chem. Soc.
VOL:1940 PAGE : 1390 -1393 (1940)
[TOP]

[0794]
AUTHOR:Marker,R.E.,Whitmore,F.C.,and Kamm,O.
TITLE:Androsterone and related sterols.
JOURNAL:J. Am. Chem. Soc.
VOL:57 PAGE : 2358 -2360 (1935)
[TOP]

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