Moxestrol Chemical Properties

Melting point:

280°

alpha 

D20 +29° (c = 0.6 in ethanol)

Boiling point:

404.46°C (rough estimate)

Density 

1.1348 (rough estimate)

refractive index 

1.4700 (estimate)

pka

10.16±0.70(Predicted)

Moxestrol Usage And Synthesis

Originator

Surestryl,Roussel,France,1974

Definition

ChEBI: Moxestrol is a 3-hydroxy steroid.

Manufacturing Process

(A) Preparation of 11β-Methoxy-?4,9-Estradiene-3,17-Dione: 0.5 g of ?4,9- estradiene-11β-ol-3,17-dione were dissolved at room temperature in 25 cc of methylene chloride containing 2% of methanol and after 5 mg of p-toluenesulfonic acid were added, the reaction mixture was agitated for several minutes. Then the reaction mixture was poured into ice water, washed with water until the wash waters were neutral, and distilled to dryness under vacuum. The resulting residue was crystallized from ethyl ether to obtain 0.46 g of 11β-methoxy-?4,9-estradiene-3,17-dione having a MP of 140°C.
(B) Preparation of 11β-Methoxy-?1,3,5(10)-Estradiene-3-ol-17-one: 12.3 g of 11β-methoxy-?4,9-estradiene-3,17-dionewere dissolved in 1,230 cc of methanol and then, under an atmosphere of nitrogen, 7.38 g of palladium hydroxide were added and the mixture was held at reflux for one hour under agitation and a nitrogen atmosphere. Then the reaction mixture was cooled to 30°C, filtered, vacuum filtered and washed with methanol. The methanolic solutions were concentrated to about 50 cc, allowed to stand overnight at room temperature and filtered. The precipitate formed was triturated in methanol and dried at 80°C to obtain 10.74 g (yield = 87.5%) of 11β- methoxy-?1,3,5(10)-estradiene-3-ol-17-one having a MP of 264°C.
(C)Preparation of 11β-Methoxy-17α-Ethynyl-?1,3,5(10)-Estradiene-3,17β-Diol: Under agitation and an atmosphere of nitrogen, 12 g of potassium were heated at 80°C in 180 cc of tertiary-amyl alcohol. The mixture was agitated for 30 minutes, cooled to 20°C and after 60 cc of dioxane were added thereto, a stream of acetylene was allowed to bubble through the mixture for one hour and fifteen minutes. Then a solution of 3 g of 11β-methoxy-?1,3,5(10)- estradiene-3-ol-17-one in 50 cc of dioxane was added and the mixture was agitated for 4 hours while continuing the passage of acetylene at room temperature. Thereafter, 50 cc of a 50% aqueous acetic acid solution was added and the mixture was poured into water and extracted with ether. The organic phases were washed first with an aqueous solution containing 10% of neutral sodium carbonate, then with water until the wash waters were neutral, dried over sodium sulfate and concentrated under vacuum until crystallization started. The reaction mixture was iced for one hour, vacuum filtered and the precipitate dried under vacuum to obtain 3.8 g of the raw 17α-ethynyl derivative, which was purified by dissolution in ethyl acetate at reflux and by icing to obtain 2.33 g (yield = 77%) of 11β-methoxy-17α-ethynyl-?1,3,5(10)- estradiene-3,17β-diol, having a MP of 280°C.

Therapeutic Function

Estrogen

Moxestrol(34816-55-2)Related Product Information

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