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Steroid


DATA No : SST0011 INFORMANT : Hideaki Nishino

NAME : 3-Hydroxyestra-1,2,5(10),7-tetraen-17-one / 1,3,5,7-Estratetraen-3-ol-17-one

COMMON NAME: Equilin
SYMBOL:
FORMULA: C18H20O2 MOL.WT (average) : 268.350


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BIOLOGICAL ACTIVITY
Weaker than estron, stronger than estriol. (Ref. 0091) Clinically available because of mild estrogenic hormone activity. (Ref. 0093)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:237-239degC (Ref. 0087) 238-240degC (Ref. 0088) 237-240degC (Ref. 0089)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]15/D=+308 (dioxane) (Ref. 0088) [a]25/D=+304deg(dioxane) (Ref. 0087) [a]/D=+295deg(c=1 in ethanol) (Ref. 0089)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:max. 283-285nm (Ref. 0090) 282nm (ethanol) (Ref. 0089)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:loge=3.36 (282nm) (Ref. 0089)
CHROMATOGRAM DATA

SOURCE
Urine of mares. (Ref. 0088/0091)
CHEMICAL SYNTHESIS
Synthesis from 19-nortestosterone acetate via four intermediates. (Ref. 0089) Relatively simple synthesis from dienone compound. (Ref. 0092) Synthesis from estratetraene via several novel steroid intermediates and reactions. (Ref. 0093) Total synthesis from estra-1,3,5(10),8-tetraenes by oxidation with m-chloroperbenzoic acid, rearrangement of the resulting epoxide with acid, catalytic hydrogenation, and dehydration. (Ref. 0094) Synthesis by conversion of equilenine. (Ref. 0095/0096)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0087]
AUTHOR:Pearlman,W.H., and Wintersteiner,O.
TITLE:Estrogens with Oxygen in Ring B I. 7-Ketoestrone and 7-Hydroxyestrone.
JOURNAL:J.Biol.Chem.
VOL:130 PAGE : 35 -45 (1939)
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[0088]
AUTHOR:Girard,A., Sandulesco,G., Fridenson,A., and Rutgers,J.-J.
TITLE:Sur Une Nouvelle Hormone Sexuelle Cristallisee.
JOURNAL:Compt.rend.
VOL:195 PAGE : 981 -984 (1932)
[TOP]

[0089]
AUTHOR:Zderic,J.A., Bowers,A., Carpio,H., and Djerassi,C.
TITLE:Steroids. XCVI. The Synthesis of Equilin.
JOURNAL:J.Am.Chem.Soc.
VOL:80 PAGE : 2596 -2597 (1958)
[TOP]

[0090]
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), pp570-570, MERCK & CO., Inc. Rahway, N.J.
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[0091]
AUTHOR:Cartland,G.F., and Meyer,R.K.
TITLE:A Study of Equilin Prepared from Pregnant Mare Urine.
JOURNAL:J.Biol.Chem.
VOL:112 PAGE : 9 -14 (1935)
[TOP]

[0092]
AUTHOR:Bagri,J.F., Morand,P.F., Wiesner,K., and Gaudry,R.
TITLE:A Simple Synthesis of Equilin.
JOURNAL:Tetrahedron Lett.
VOL:1964 PAGE : 387 -389 (1964)
[TOP]

[0093]
AUTHOR:Stein,R.P., Buzby,Jr.,G.C., and Smith,H.
TITLE:A New Total Synthesis of Equilin.
JOURNAL:Tetrahedron Lett.
VOL:1966 PAGE : 5015 -5020 (1966)
[TOP]

[0094]
AUTHOR:Stein, R. P., Buzby, G. C., Jr., and Smith, H.
TITLE:Totally synthetic steroid hormones. XX. Novel total syntheses of equilin and equilenin PubMed ID:5433528
JOURNAL:Tetrahedron.
VOL:26 PAGE : 1917-1933 (1970)
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[0095]
AUTHOR:Bailey,E.J., Gale,A., Phillipps,G.H., Siddons,P.T., and Smith,G.
TITLE:Syntheses of Equilenin, Equilin, and 17b-Hydroxyoestr-4-En-3-One.
JOURNAL:J.Chem.Soc., Chem.Commun.
VOL:1967 PAGE : 1253 -1254 (1967)
[TOP]

[0096]
AUTHOR:Marshall,D.J., and Deghenghi,R.
TITLE:A New Direct Synthesis of Equilin from Equilenin. Potassium-Ammonia Reduction of Some Non-Conjugated Double Bonds.
JOURNAL:Can.J.Chem.
VOL:47 PAGE : 3127 -3131 (1969)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.