The nature of the oestrogenic substances produced during the demethylation of anethole

Abstract

The discovery of oestrogenic activity in synthetic substances not possessing the phenanthrene nucleus led eventually to interest in derivatives of stilbene, notably 4:4’ -dihydroxy-stilbene, and in para alkyl substituted phenols (Dodds and Lawson 1937 a ; Dodds, Fitzgerald and Lawson 1937). It was noted that p -propenyl phenol (anol) was a member of the latter series but in addition possessed structural similarity to the former. The substance was accordingly prepared and tested for oestrogenic activity, the potency being found of the same order as that of oestrone (Dodds and Lawson 1937 b ). Following this publication numerous workers repeated the preparation but reports on the activity were conflicting. Confirmation of the original announcement was forthcoming from several laboratories but others were quite unable to obtain similar results. A reinvestigation of the subject showed that while certain batches of crystalline material had high oestrogenic activity, others were very much less active.