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Steroid


DATA No : SST0005 INFORMANT : Hideaki Nishino

NAME : Dihydroxycholesterol / 3b-Hydroxycholestan / 5a-Cholestan-3b-ol

COMMON NAME: Cholestanol / b-Cholestanol
SYMBOL:
FORMULA: C27H48O1 MOL.WT (average) : 388.669


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BIOLOGICAL ACTIVITY
Accumulation within the nervous system in cerebrotendinous xanthomatosis patients. (Ref. 0031)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:141.5-142degC (Ref. 0026)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a] 22/D=+28.8deg (Ref. 0026)

DENSITY:

SOLUBILITY:Freely sol in heated alcohol, ethylether, chloroform. Approximately 1 g/100 ml alcohol or 200 ml methanol. (Ref. 0028)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:9.20(19-H), 9.36(18-H) (Ref. 0029)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Human feces, bilestones, eggs. (Ref. 0028) Trace amount accompanied with cholesterol in animal cells, predominant sterol of sponges. (Ref. 0030)
CHEMICAL SYNTHESIS
Synthesis by reduction of cholesterol. (Ref. 0026/0027)
METABOLISM

GENETIC INFORMATION

NOTE
Precipitable by digitonin. Negative in Liebermann-Burchard reaction. (Ref. 0026/0027)
REFERENCES
[0026]
AUTHOR:Willstätter,R., and Mayer,E.W.
TITLE:Reduktion Mit Platin und Wasserstoff. II. Über Dihydrocholesterin.
JOURNAL:Ber.
VOL:41 PAGE : 2199 -2203 (1908)
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[0027]
AUTHOR:Ellis,G.W., and Gardner,J.A.
TITLE:On b-Cholestanol, Some of Its Derivatives and Oxidation Products.
JOURNAL:Biochem.J.
VOL:12 PAGE : 72 -80 (1918)
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[0028]
AUTHOR:Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp341-341, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0029]
AUTHOR:Tori,K., Komeno,T., and Nakagawa,T.
TITLE:Nuclear Magnetic Resonance Studies on Steroids. III. Steroidal Epoxides and Episulfides
JOURNAL:J.Org.Chem.
VOL:29 PAGE : 1136 -1141 (1964)
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[0030]
AUTHOR:Rosenfeld, R. S.
TITLE:Analysis of sterol extracts for cholestanol PubMed ID:5323673
JOURNAL:Anal Biochem.
VOL:12 PAGE : 483-487 (1965)
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[0031]
AUTHOR:Menkes, J. H., Schimschock, J. R., and Swanson, P. D.
TITLE:Cerebrotendinous xanthomatosis. The storage of cholestanol within the nervous system PubMed ID:5676919
JOURNAL:Arch Neurol.
VOL:19 PAGE : 47-53 (1968)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.