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Steroid


DATA No : SST0016 INFORMANT : Hideaki Nishino

NAME : 4-Methylstigmasta-7,24(28)-dien-3-ol

COMMON NAME: a1-Sitosterol / Citrostadienol
SYMBOL:
FORMULA: C30H50O1 MOL.WT (average) : 426.717


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:164-166degC (free), 137degC (acetate), 168-172degC (benzoate) (Ref. 0136/0139)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]28/D = -1.7 (c=2 in chloroform), [a]25/D = -1.7 (acetate) (Ref. 0136/0139)

DENSITY:

SOLUBILITY:Sol in alcohol, benzene, pyridine (Ref. 0139)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:m/e more than 200%: M(3), M-15(3), M-(15+18)(-), M-98(57), M=(98+15)(8), M-(98+18)(3), M-127(3), M-(98+15+18)(4), M-141(100), M-(139+18)(8), M-(141+18)(7), M-165(10), M-181(6), M-(165+18)(3), M-184(2), M-185(3), M-(181+18)(9) (Ref. 0140)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Wheat germ oil (Ref. 0139/0141), Corn oil (Ref. 0142), Plants (Ref. 0143)
CHEMICAL SYNTHESIS
Synthesis from D7-cholesten-3-one by methylation and reduction. (Ref. 0138)
METABOLISM

GENETIC INFORMATION

NOTE
Stereochemistry. (Ref. 0140) Precipitable by digitonin. (Ref. 0143) Same compound as citrostadienol. (Ref. 0144/0145)
REFERENCES
[0136]
AUTHOR:Bernstein,S., and Wallis,E.S.
TITLE:Studies in the Sitosterol Complex. The Structure of a1-Sitosterol.
JOURNAL:J.Am.Chem.Soc.
VOL:61 PAGE : 2308 -2313 (1939)
[TOP]

[0138]
AUTHOR:Mazur,Y., and Sondheimer,F.
TITLE:Synthesis of 4a-Methyl-D7-Steroids. The Interrelationship of Cholesterol, Citrostadienol and Lophenol.
JOURNAL:J.Am.Chem.Soc.
VOL:80 PAGE : 6292 -6299 (1958)
[TOP]

[0139]
AUTHOR:Wallis,E.S., and Fernholz,E.
TITLE:a-Sitosterol.
JOURNAL:J.Am.Chem.Soc.
VOL:58 PAGE : 2446 -2448 (1936)
[TOP]

[0140]
AUTHOR:Brooks, C. J., Knights, B. A., Sucrow, W., and Raduchel, B.
TITLE:The characterisation of 24-ethylidene-sterols PubMed ID:5085133
JOURNAL:Steroids.
VOL:20 PAGE : 487-497 (1972)
[TOP]

[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)
[TOP]

[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)
[TOP]

[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]

[0144]
AUTHOR:Schreiber,K., and Osske,G.
TITLE:Isolierung von 4a-Methyl-5a-Stigmasta-7,24(28)-Dien-3b-Ol aus Solanum Tuberosum Sowie Über die Identität dieser Verbindung mit a1-Sitosterin.
JOURNAL:Experientia
VOL:19 PAGE : 69 -71 (1963)
[TOP]

[0145]
AUTHOR:Schreiber,K., and Osske,G.
TITLE:Sterine und Triterpenoide V Über die 4a-Methyl-Sterine der Kartoffelpflanze Solanum Tuberosum L.
JOURNAL:Tetrahedron
VOL:20 PAGE : 2575 -2584 (1964)
[TOP]

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