ATC code None PubChem CID 6271 Molar mass 150.175 g/mol | CAS Number 70-70-2 ChemSpider 6035 | |
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Legal status In general: ℞ (Prescription only) Synonyms NSC-2834, 4'-hydroxypropiophenone, ethyl p-hydroxyphenyl ketone, p-propionylphenol, paroxypropiophenone | ||
Paroxypropione is a manufactured, non-steroidal estrogen that has been used medically as an antigonadotropin in Spain and Italy. Paroxypropione was first synthesized in 1902. Its antigonadotropic properties were discovered in 1951 and it entered clinical use shortly thereafter.
Contents
Paroxypropione is closely related structurally to p-hydroxybenzoic acid and parabens such as methylparaben, and also bears a close resemblance to diethylstilbestrol (which, in fact, produces paroxypropione as an active metabolite) and alkylphenols like nonylphenol, all of which are also estrogens. The drug possesses relatively low affinity for the estrogen receptor and must be given at high dosages to achieve significant estrogenic and antigonadotropic action, for instance, 0.8 to 1.6 g/day. It possesses 0.1% of the estrogenic activity of estrone and less than 0.5% of the antigonadotropic activity of estrone.
Similarly to p-hydroxybenzoic acid, paroxypropione has been found to possess antioxidant activity.
Synthesis
In the best case, a ~96% yield was reported from the reaction between phenol and propionyl chloride. The mechanism is likely to involve initial ester formation, followed by a Fries rearrangement.
Names
Brand names Frenantol, Frenormon, Hypophenon, Paroxon, Possipione, Profenone, numerous others; former developmental code name NSC-2834), also known as paroxypropiophenone (P.O.P.) or 4'-hydroxypropiophenone.
Derivatives
Paroxypropione is a precursor in the chemical synthesis of:
- Non-steroidal stilbene estrogens including: diethylstilbestrol, dienestrol and Hexestrol
- Fenalcomine
- Buphenine which itself is a precursor to Bufeniode.
- Ractopamine
- A patent for para-hydroxy-phenylpropanolamine was also disclosed.