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Steroid


DATA No : SST0167 INFORMANT : Hideaki Nishino

NAME : 5b-cholestane

COMMON NAME: Coprostane / Pseudocholestane
SYMBOL:
FORMULA: C27H48 MOL.WT (average) : 372.670


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BIOLOGICAL ACTIVITY
Yielded coprostane (55%) and cholestane (45%) by hydrogenation of cholest-4-ene in the presence of ethanol, platinum, and sodium nitrite. (Ref. 0040) Synthesis by hydrogenation of D6-coprostene. (Ref. 0704) Synthesis by reduction of coprostan-3-one. (Ref. 0705)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:72degC (alcohol) (Ref. 0702)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]11/D=+25.1deg (c=2 in chloroform) (Ref. 0040)

DENSITY:

SOLUBILITY:Sol in ether, chloroform. Sparingly sol in anhydrous alcohol. (Ref. 0702/0703/0040/0704/0705)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:Characteristic bands at 900 and 1070/cm. (Ref. 0040)

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0040]
AUTHOR:Dart,M.C., and Henbest,H.B.
TITLE:Aspects of Stereochemistry. Part XV. Catalytic Hydrogenation of Cyclic Allylic Alcohols in the Presence of Sodium Nitrite.
JOURNAL:J.Chem.Soc.
VOL:1960 PAGE : 3563 -3570 (1960)
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[0702]
AUTHOR:Wieland,H.,and Jacobi,R.
TITLE:Die Synthese des Pseudo-cholestans aus Cholansäure.
JOURNAL:Ber.
VOL:59 PAGE : 2064 -2067 (1926)
[TOP]

[0703]
AUTHOR:Young,W.G.,Ireland,R.E.,Wrigley,T.I.,Shoppee,C.W.,Agashe,B.D.,and Summers,G.H.R.
TITLE:Allylic rearrangements. XLII. The preparation and some reactions of 3b-chlorocholest-4-ene and 3a-chlorocholest-4-ene.
JOURNAL:J. Am. Chem. Soc.
VOL:81 PAGE : 1452 -1454 (1959)
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[0704]
AUTHOR:Nickon,A.,and Bagli,J.F.
TITLE:Reactivity and geometry in allylic systems. I. Stereochemistry of photosensitized oxygenation of monoölefins.
JOURNAL:J. Am. Chem. Soc.
VOL:83 PAGE : 1498 -1508 (1961)
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[0705]
AUTHOR:Caglioti,L.,and Grasselli,P.
TITLE:A new method for the reduction of aldehydes and ketones to CH2 under mild conditions.
JOURNAL:Chem. Ind. (London)
VOL:1964 PAGE : 153 -153 (1964)
[TOP]

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