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Steroid


DATA No : SST0017 INFORMANT : Hideaki Nishino

NAME : Stigmast-5-en-3b-ol

COMMON NAME: b-Sitosterol / 22:23-Dihydrostigmasterol
SYMBOL:
FORMULA: C29H50O1 MOL.WT (average) : 414.707


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BIOLOGICAL ACTIVITY
Antihyperlipoproteinemic agent, for prostate tumor therapy. (Ref. 0154/0155/0156) Inhibition to cholesterol absorption. (Ref. 0158/0159) Inhibition of carcinogenesis. (Ref. 0160)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:140degC, 127-128degC (acetate) (Ref. 0143) 136-137degC (Ref. 0147)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]25/D = -37deg (c = 2 in chloroform) (Ref. 0143) -41deg (acetate) (Ref. 0147)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:TMS-derivatives (MW = 486): 129(100%), 357(98%), 396(66%), 121(58%), 145(45%), 215(42%) (Ref. 0148)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Wheat germ oil, corn oil (Ref. 0142) Rye germ oil (Ref. 0149) Cotton seed oil (Ref. 0150) Tall oil (Ref. 0151) Soybean, calabar bean, rice germ (Ref. 0152) Cascara (Rhamnus purshiana) (Ref. 0153) Cinchona bark, Cinchona wax (Ref. 0153)
CHEMICAL SYNTHESIS
Stereospecific synthesis 24-ethylcholesta-5,22,25-trien-3b-ol by hydrogenation and ring opening. (Ref. 0157)
METABOLISM

GENETIC INFORMATION

NOTE
Precipitable by digitonin. (Ref. 0143/0146/0147)
REFERENCES
[0142]
AUTHOR:Anderson,R.J., Shriner,R.L., and Burr,G.O.
TITLE:The Phytosterols of Wheat Germ.
JOURNAL:J.Am.Chem.Soc.
VOL:48 PAGE : 2987 -2996 (1926)
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[0143]
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), pp1353-1353, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0146]
AUTHOR:Shoppee,C.W.
TITLE:Steroids and the Walden Inversion. Part III. (a) Derivatives of 6-Ketocholestane; (b) a Direct Proof of the Stereochemical Orientation of the Hydroxyl Group in Cholesterol.
JOURNAL:J.Chem.Soc.
VOL:1948 PAGE : 1032 -1043 (1948)
[TOP]

[0147]
AUTHOR:Bernstein,S., and Wallis,E.S.
TITLE:Nature of b-Sitosterol , and Its Preparation from Stigmasterol.
JOURNAL:J.Org.Chem.
VOL:2 PAGE : 341 -345 (1937)
[TOP]

[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)
[TOP]

[0149]
AUTHOR:Gloyer,S.W., and Schuette,H.A.
TITLE:The Sterols of Rye Germ Oil.
JOURNAL:J.Am.Chem.Soc.
VOL:61 PAGE : 1901 -1903 (1939)
[TOP]

[0150]
AUTHOR:Wallis,E.S., and Chakravorty, P.N.
TITLE:The Nature of the Sterols in Cottonseed Oil.
JOURNAL:J.Org.Chem.
VOL:2 PAGE : 335 -340 (1937)
[TOP]

[0151]
AUTHOR:Sandqvist,H., and Bengtsson,E.
TITLE:Zur Frage der Bruttoformel des Sitosterins.
JOURNAL:Ber.
VOL:64 PAGE : 2167 -2171 (1931)
[TOP]

[0152]
AUTHOR:Tanaka,K.
TITLE:Über die Sterine des Reisembryos.
JOURNAL:J.Biochem.
VOL:17 PAGE : 483 -494 (1933)
[TOP]

[0153]
AUTHOR:Dirscherl,W.
TITLE:Über die Konstitution des Cinchols; Seine Über Führung in 3-Oxy-Ätio-Allocholanon-(17). 3. Mitteilung Über Sexualhormone und Verwandte Stoffe.
JOURNAL:Z.Physiol.Chem.
VOL:235 PAGE : 1 -7 (1935)
[TOP]

[0154]
AUTHOR:Greten,H.(1976) Lipoprotein Metabolism (Greten,H., eds.), pp119-124, Springer-Verlag, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0155]
AUTHOR:Greten,H.(1976) Lipoprotein Metabolism (Greten,H., eds.), pp125-130, Springer-Verlag, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0156]
AUTHOR:Szutrely, H. P.
TITLE:[Changes in the echostructure of prostatic adenomas during drug therapy] PubMed ID:6182449
JOURNAL:Med Klin [Prax].
VOL:77 PAGE : 42-46 (1982)
[TOP]

[0157]
AUTHOR:Sucrow,W., and Slopianka,M.
TITLE:b-Sitosterin und Clionasterin aus (24R)-Bzw. (24S)-24-Äthylcholesta-5,22,25-Trien-3b-Ol.
JOURNAL:Chem.Ber.
VOL:108 PAGE : 3721 -3729 (1975)
[TOP]

[0158]
AUTHOR:Greten,H.(1976) Lipoprotein Metabolism (Greten,H., eds.), pp112-118, Springer-Verlag, New York
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0159]
AUTHOR:Ikeda, I., and Sugano, M.
TITLE:Some aspects of mechanism of inhibition of cholesterol absorption by beta-sitosterol PubMed ID:6615593
JOURNAL:Biochim Biophys Acta.
VOL:732 PAGE : 651-658 (1983)
[TOP]

[0160]
AUTHOR:Nigro, N. D., Bull, A. W., Wilson, P. S., Soullier, B. K., and Alousi, M. A.
TITLE:Combined inhibitors of carcinogenesis: effect on azoxymethane-induced intestinal cancer in rats PubMed ID:6954303
JOURNAL:J Natl Cancer Inst.
VOL:69 PAGE : 103-107 (1982)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.