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Steroid


DATA No : SST0018 INFORMANT : Hideaki Nishino

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

COMMON NAME: g-Sitosterol / Clionasterol
SYMBOL:
FORMULA: C29H50O1 MOL.WT (average) : 414.707


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BIOLOGICAL ACTIVITY
Anticholesteremic. (Ref. 0161/0162)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:147-148degC (alcohol) (Ref. 0162/0163/0164)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]20/D = -43deg (c=1.9 in chloroform) (Ref. 0162/0163/0164)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Corn oil (Ref. 0141) Predominant sterol of soybean oil (Ref. 0162)
CHEMICAL SYNTHESIS
Stereospecific synthesis 24-ethylcholesta-5,22,25-trien-3b-ol by hydrogenation and ring opening. (Ref. 0157)
METABOLISM

GENETIC INFORMATION

NOTE
Different stereoconfiguration in C-24 from b-sitosterol. (Ref. 0165)
REFERENCES
[0141]
AUTHOR:Anderson,R.J., and Shriner,R.L.
TITLE:The Phytosterols of Corn Oil.
JOURNAL:J.Am.Chem.Soc.
VOL:48 PAGE : 2976 -2986 (1926)
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[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)
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[0161]
AUTHOR:Pavanaram,S.K., Hofer,P., Linde,H., and Meyer,K.
TITLE:Die Glykoside der Blätter von Digitalis Canariensis L., Var. Isabelliana (Webb) Lindinger 2. Mitteilung.
JOURNAL:Helv.Chim.Acta
VOL:46 PAGE : 1377 -1385 (1963)
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[0162]
AUTHOR:Bonstedt,K.
TITLE:Über Einige Sterine des Pflanzenreichs.
JOURNAL:Z.Physiol Chem.
VOL:176 PAGE : 269 -281 (1928)
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[0163]
AUTHOR:Dirscherl,W.
TITLE:Vergleich von Cinchol (Sterin der Chinarinde) mit Sitosterin und Stigmasterin 12. Mitteilung Über Sexualhormone und Verwandte Stoffe [Sterine].
JOURNAL:Z.Physiol.Chem.
VOL:257 PAGE : 239 -245 (1939)
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[0164]
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), pp1354-1354, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0165]
AUTHOR:Bergmann,W., and Low,E.M.
TITLE:Contributions to the Study of Marine Products. XX. Remarks Concerning the Structure of Sterols from Marine Invertebrates.
JOURNAL:J.Org.Chem.
VOL:12 PAGE : 67 -75 (1947)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.