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Steroid


DATA No : SST0067 INFORMANT : Hideaki Nishino

NAME : 3-Hydroxyestra-1,3,5(10)-trien-17-one / 1,3,5-Estratrien-3-ol-17-one

COMMON NAME: Estrone
SYMBOL:
FORMULA: C18H22O2 MOL.WT (average) : 270.366


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BIOLOGICAL ACTIVITY
Synthesis from cholesterol. (Ref. 0123) Improved protocols for synthesis of 19-norsteroids. (Ref. 0388) Synthesis via bicyclo[2,2,1]heptane as an intermediate. (Ref. 0135) Synthesis by application of boron annulation. (Ref. 0389)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:dl-form: 251-254deg (acetone), d-form: 254.5-256deg (acetone) (Ref. 0123) 254.5-256deg (acetone) (Ref. 0123)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]22/D=+152deg (c=0.995 in chloroform) (Ref. 0123)

DENSITY:

SOLUBILITY:Sol in water (25deg): 0.003g/100ml. Sol in 96% alcohol 250ml, acetone 50ml, chloroform 110ml (1g estrone, 15degC). Sol in alcohol 50ml, benzene 145ml (1g estrone, boiling). Sol in dioxane, pyridine, fixed alkali hydroxide. Slightly sol in ether, vegetable oils. (Ref. 0123)
SPECTRAL DATA
UV SPECTRA:UVmax: 283-285nm (Ref. 0384)

IR SPECTRA:Infrared spectra of estrone methyl esters. (Ref. 0385)

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Found in pregnant women, pregnant mares, follicular fluids from many animals, human placenta, urine of bulls and studhorses, palm-kernek oil (Ref. 0121/0386) Roots of moghat (Clossostemon bruguieri, Sterculiaceae), pollens of Egyptian date palm (Phoenix dactylifera). (Ref. 0387)
CHEMICAL SYNTHESIS

METABOLISM
Estrogenic activity. (Ref. 0121/0386)
GENETIC INFORMATION

NOTE
Ppt with digitonin. (Ref. 0123)
REFERENCES
[0121]
AUTHOR:Butenandt,A.
TITLE:Über Progynon Ein Krystallisiertes Weibliches Sexualhormon.
JOURNAL:Naturwiss.
VOL:17 PAGE : 879 -879 (1929)
[TOP]

[0123]
AUTHOR:Anner,G., and Miescher,K.
TITLE:Über Steroide. 83. Mitteilung. Die Synthese des Natürlichen Oestrons. Total Synthesen in der Oestronreihe III.
JOURNAL:Helv.Chim.Act
VOL:31 PAGE : 2173 -2183 (1948)
[TOP]

[0135]
AUTHOR:Grieco,P.A., Takigawa,T., and Schillinger,W.J.
TITLE:Bicyclo [2,2,1] Heptanes as Intermediates in the Synthesis of Steroids. Total Synthesis of Estrone.
JOURNAL:J.Org.Chem.
VOL:45 PAGE : 2247 -2251 (1980)
[TOP]

[0384]
AUTHOR:Anner,G.,and Miescher,K.
TITLE:Über Steroide. 98. Mittelung. Zur Konstitution der Synthetischen Oestronracemate. Totalsynthesen in der Oestronreihe V.
JOURNAL:Helv. Chim. Acta
VOL:33 PAGE : 1379 -1385 (1950)
[TOP]

[0385]
AUTHOR:Johnson,W.S.,David,I.A.,Dehm,H.C.,Highet,R.J.,Warnhoff,E.W.,Wood,W.D.,and Jones,E.T.
TITLE:Configuration of the estrones. Total synthesis of the remaining stereoisomers.
JOURNAL:J. Am. Chem. Soc.
VOL:80 PAGE : 661 -679 (1958)
[TOP]

[0386]
AUTHOR:Doisy,E.A.,Veler,C.D.,and Thayer,S.
TITLE:Folliculin from urine of pregnant women.
JOURNAL:Am. J. Physiol.
VOL:90 PAGE : 329 -330 (1929)
[TOP]

[0387]
AUTHOR:Amin,El S.,Awad,O.,Abd El Samad,M.,and Iskander,M.N.
TITLE:Isolation of estrone from Moghat roots and from pollen grains of Egyptian date palm.
JOURNAL:Phytochemistry
VOL:8 PAGE : 295 -297 (1969)
[TOP]

[0388]
AUTHOR:Windholz,T.B.,and Windholz,M.
TITLE:Recent advances in the synthesis of 19-norsteroids.
JOURNAL:Angew. Chem. Int. Ed.
VOL:3 PAGE : 353 -361 (1964)
[TOP]

[0389]
AUTHOR:Bryson,T.A.,and Reichel,C.J.
TITLE:Boron annulation: Total synthesis of (pm)-estrone methyl ether.
JOURNAL:Tetrahedron Lett.
VOL:21 PAGE : 2381 -2384 (1980)
[TOP]

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