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Steroid


DATA No : SST0019 INFORMANT : Hideaki Nishino

NAME : Stigmasta-5,22-dien-3b-ol

COMMON NAME: Stigmasterol, Anti-stiffness factor / 3b-Hydroxy-24-ethyl-D5,22-cholestadiene
SYMBOL:
FORMULA: C29H48O1 MOL.WT (average) : 412.691


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BIOLOGICAL ACTIVITY
Antistiffness factor. (Ref. 0177)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:144.0-144.6degC (acetate), 170degC (free) (Ref. 0170/0171/0172)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]22/D = -51deg (c = 2 in chloroform), [a]20/D = -55.6deg(acetate, c = 2 in chloroform) (Ref. 0171/0172)

DENSITY:

SOLUBILITY:Insol in water. Sol in organic solvents (Ref. 0172)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:TMS : 484(22%), 394(35%), 255(63%), 145(32%), 133(38%), 129(100%) (Ref. 0148)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Distributed widely in plant kingdom. Calabar beans (Physostigma venenosum). (Ref. 0173) Kidney beans (Phaseolus vulgaris). (Ref. 0174) Oils from corn, coconuts, rapeseed, and soybeans. (Ref. 0170/0175/0176)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
Simple purification as acetic ester bromide because of the insolubility in ethylether. (Ref. 0178)
REFERENCES
[0148]
AUTHOR:Steel, G., and Henderson, W.
TITLE:Rapid method for detection and characterization of steroids PubMed ID:4658153
JOURNAL:Anal Chem.
VOL:44 PAGE : 1302-1304 (1972)
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[0170]
AUTHOR:Deuel,Jr.,H.J.(1951) Waxes, Higher Alcohols including Sterols, Triterpenes, Glyceryl Ethers, Colored Fats, and Hydrocarbons in the Lipids Their Chemistry and Biochemistry I (Deuel,Jr.,H.J., eds) pp305-404, Interscience Publishers, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0171]
AUTHOR:Sandqvist,H., and Gorton,J.
TITLE:Stigmasterol and Its Empirical Formula.
JOURNAL:Ber.
VOL:63 PAGE : 1935 -1938 (1930)
[TOP]

[0172]
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), pp1388-1388, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0173]
AUTHOR:Windaus,A., and Hauth,A.
TITLE:Ueber Stigmasterin, Ein Neues Phytosterin aus Calabar-Bohnen.
JOURNAL:Ber.
VOL:39 PAGE : 4378 -4384 (1906)
[TOP]

[0174]
AUTHOR:Otto,A.C., and Ball,C.D.
TITLE:The Isolation of Stigmasterol and b-Sitosterol from the Common Bean, Phaseolus Vulgaris.
JOURNAL:J.Am.Chem.Soc.
VOL:66 PAGE : 489 -491 (1944)
[TOP]

[0175]
AUTHOR:Byerrum,R.U., and Ball,C.D.
TITLE:Stigmasterol.
JOURNAL:Biochem.Prepns.
VOL:7 PAGE : 86 -88 (1959)
[TOP]

[0176]
AUTHOR:Thornton,M.H., Kraybill,H.R., and Mitchell,Jr.,J.H.
TITLE:Sterol Glucosides from Expressed Soybean Oil.
JOURNAL:J.Am.Chem.Soc.
VOL:62 PAGE : 2006 -2008 (1940)
[TOP]

[0177]
AUTHOR:Rosenkrantz,H., Milhorat,A.T., Farber,M., and Milman,A.E.
TITLE:Purification and Identification of the Antistiffeness Factor.
JOURNAL:Proc.Soc.Exptl.Biol.Med.
VOL:76 PAGE : 408 -410 (1951)
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[0178]
AUTHOR:Colin,H., Guiochon,G., and Siouffi,A.
TITLE:Comparison of Various Systems for the Separation of Free Sterols by High Performance Liquid Chromatography.
JOURNAL:Anal.Chem.
VOL:51 PAGE : 1661 -1666 (1979)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.