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Steroid


DATA No : SST0015 INFORMANT : Hideaki Nishino

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

COMMON NAME: Estrone / Oestrone / Theelin / Folliculin / Follicular hormone / Tokokin / Thelykinin / Ketohydroxyestrin / Hiestrone / Menformon / Glandubolin / Cristallovar / Destrone / Endofolliculina / Estrol / Femidyn / Folikrin / Ovex / Kolpon / Crinovaryl / Folisan / Disynformon / Hormovarine / Oestroperos / Wynestron / Thelestrin / Kestrone / Estrusol / Estrugenone / Femestrone INJ. / Folipex / Follestrine / Follidrin / Follicunodis / Hormofollin / Oestrin / Oestroform / Ovifollin / Perlatan / Ketodestrin / Unden
SYMBOL:
FORMULA: C18H22O2 MOL.WT (average) : 270.366


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BIOLOGICAL ACTIVITY
One of estrogenic hormones. Same potent as estriol, less potent than estradiol-17b. (Ref. 0121/0122/0124/0127)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:254.5-256degC (acetone), 240degC (azoate) (Ref. 0123/0124)

BOILING POINT:

REFRACTIVE INDEX:[a]22/D=+152deg (Ref. 0123)

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:3g sol in 100 ml water (25degC), 1g sol in 96% alcohol (15degC) 250ml, boiling alcohol 50ml, acetone 50ml (15degC), chloroform 110 ml (15degC), boiling benzene 145ml. Sol in diozane, pyridine, fixed alkali hydroxides. Slightly sol in ether, vegetable oils. (Ref. 0125)
SPECTRAL DATA
UV SPECTRA:max. 282, 296nm(p-dioxane, e=2300, 2130); 300, 450nm (conc.sulfate); 239, 293nm (0.1M NaOH) (Ref. 0125)

IR SPECTRA:nmax (CHCl3): 1,693/cm (methyl ether) (Ref. 0126)

NMR SPECTRA:(chloroform)d: 1.08 (3H,s,-CH3), 3.69 (3H,s,OCH3), 6.39-6.72 (2H,m,C2H), 7.08 (1H,d,J=9Hz,C,H) (methyl ether) (Ref. 0126)

MASS SPECTRA:m/e 298 (M+) (methyl ether) (Ref. 0126)

OTHER SPECTRA:E1%/1cm=77 (280nm, e = 2,080) (Ref. 0105)
CHROMATOGRAM DATA

SOURCE
Pregnancy urine of human and mares, follicular liquor of animals, human placenta, urine from bulls and stallions palm-kernel oil, date palm pollen grains. (Ref. 0120/0122/0124/0127) Moghat roots. (Ref. 0124)
CHEMICAL SYNTHESIS
Stereospecific synthesis from b-m-anisylethylmalonic ester by condensation if the sodio derivative with the acid chloride of ethyl hydrogen glutarate. (Ref. 0128) Total synthesis from tricyclic ketoester compounds. (Ref. 0123/0129/0130/0131/0132) New synthesis methods by intramolecular cycloaddition reaction of olefinic o-quinodimethane. (Ref. 0126/0133/0134/0135)
METABOLISM

GENETIC INFORMATION

NOTE
Precipitable by digitonin. (Ref. 0121/0122)
REFERENCES
[0105]
AUTHOR:Sober,H.A., (1968) Section F Steroids in Handbook of Biochemistery Selected Data for Molecular Biology (Sober,H.A., eds.) ppF11-F11, The Chemical Rubber, Cleveland
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0120]
AUTHOR:Leeds,N.S., Fukushima,D.K., and Gallagher,T.F.
TITLE:Studies of Steroid Ring D Epoxides of Enol Acetates; A New Synthesis of Estriol and Androstane-3b, 16a,17b-Triol.
JOURNAL:J.Am.Chem.Soc.
VOL:76 PAGE : 2943 -2948 (1954)
[TOP]

[0121]
AUTHOR:Butenandt,A.
TITLE:Über Progynon Ein Krystallisiertes Weibliches Sexualhormon.
JOURNAL:Naturwiss.
VOL:17 PAGE : 879 -879 (1929)
[TOP]

[0122]
AUTHOR:Doisy,E.A., Veler,C.D., and Thayer,S.
TITLE:Folliculin from Urine of Pregnant Woman.
JOURNAL:Am.J.Physiol.
VOL:90 PAGE : 329 -330 (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]

[0124]
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]

[0125]
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), pp584-585, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0126]
AUTHOR:Kametani, T., Nemoto, H., Ishikawa, H., Shiroyama, K., and Matsumoto, H.
TITLE:A stereoselective total synthesis of estrone by an intramolecular cycloaddition reaction of olefinic o-quinodimethane PubMed ID:853183
JOURNAL:J Am Chem Soc.
VOL:99 PAGE : 3461-3466 (1977)
[TOP]

[0127]
AUTHOR:Sih,C.J., Lee,S.S., Tsong,Y.Y., Wang,K.C., and Chang,F.N.
TITLE:An Efficient Synthesis of Estrone and 19-Norsteroids from Cholesterol.
JOURNAL:J.Am.Chem.Soc.
VOL:87 PAGE : 2765 -2766 (1965)
[TOP]

[0128]
AUTHOR:Bachman,W.E., Kushner,S., and Stevenson,A.C.
TITLE:The Total Synthesis of a Stereoisomer of the Sex Hormone Estrone.
JOURNAL:J.Am.Chem.Soc.
VOL:64 PAGE : 974 -981 (1942)
[TOP]

[0129]
AUTHOR:Anner,G., and Miescher,K.
TITLE:Über Steroide. 98 Mitteilung. Zur Konstitution der Synthetischen Oestronracemate. Totalsynthesen in der Oestronreihe V.
JOURNAL:Helv.Chim.Acta
VOL:33 PAGE : 1379 -1385 (1950)
[TOP]

[0130]
AUTHOR:Anner,G., and Miescher,K.
TITLE:Über Steroide. 93. Mitteilung. Die Synthese von Weiteren Oestron-Racematen. Totalsynthesen in der Oestronreihe IV.
JOURNAL:Helv.Chim.Acta
VOL:32 PAGE : 1957 -1967 (1949)
[TOP]

[0131]
AUTHOR:Johnson,W.S., Banerjee,D.K., Schneider,W.P., and Gutsche,C.D.
TITLE:The Total Synthesis of Estrone and the Remaining Stereoisomers.
JOURNAL:J.Am.Chem.Soc.
VOL:72 PAGE : 1426 -1426 (1950)
[TOP]

[0132]
AUTHOR:Johnson,W.S., Banerjee,D.K., Schneider,W.P., Gutsche,C.D., Shelberg,W.E., and Chinn,L.T.
TITLE:The Total Synthesis of Estrone and Three Stereoisomers Including Lumiestrone.
JOURNAL:J.Am.Chem.Soc.
VOL:74 PAGE : 2832 -2849 (1952)
[TOP]

[0133]
AUTHOR:Bartlett, P. A., and Johnson, W. S.
TITLE:A stereospecific total synthesis of estrone via a cationic olefinic cyclization PubMed ID:4747883
JOURNAL:J Am Chem Soc.
VOL:95 PAGE : 7501-7502 (1973)
[TOP]

[0134]
AUTHOR:Danishefsky, S., and Cain, P.
TITLE:Optically specific synthesis of estrone and 19-norsteroids from 2,6-lutidine PubMed ID:950420
JOURNAL:J Am Chem Soc.
VOL:98 PAGE : 4975-4983 (1976)
[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]

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