The activation of female sex hormones

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Abstract
The threshold values and duration of oestrus of 9 aliphatic 3-mono-esters, 10 aliphatic, 17-mono-esters and the 17-mono-benzoate of a-oestradiol by subcutan. inj. were detd. in the oestrus test using castrated rats. The threshold values of the 17-mono-esters were generally somewhat higher than those of the corresponding 3-mono-esters. A prolonged effect was obtained particularly with the higher esters. In this respect all the 17-esters were superior to the corresponding 3-esters, the 17-octanoate (17-caprylate) exhibiting the most intense and prolonged effect even with small doses. The temporal course of the wt. of the uterus after adm. of a-oestradiol and its mono-esters was detd. on uncastrated young rats and also castrated adult rats. The results obtained with both kinds of rats agreed in an astonishing way. In this test the 17-mono-esters proved to be superior to the corresponding 3-mono-esters. The histological examination of the uterus showed that the single-layered cylindrical epithelium changed under the prolonged influence of hormone into several strata of partly keratinized cells of very high cylindrical epithelium ("vertical keratinization"). Malignant tumors were not observed. The output of activity was, e.g., with the 17-n-butyrate, 327 cg.-days and with the 17-octanoate (17-caprylate) about 1100 cg.-days, against 20.3 cg.-days for the free oestradiol and 119 cg.-days for its 3-benzoate. The prep. of the following new a-oestradiol-mono-esters was descr.: 3-n-valerate crystals with M.P. 58[degree]-60[degree], B.P. 180[degree]-190[degree] at 0.0004 mm; 3-n-hexanoate: crystals with M.P. 46[degree]-51[degree], B.P. 180[degree]-190[degree] at 0.0008 mm; 3-n-octanoate: crystals with M.P. 48[degree]-53[degree], B.P. 180[degree] at 0.0004 mm; 3-n-decanoate M.P. 59[degree]-60[degree]; 17-n-hexanoate: crystals with M.P. 128.5[degree]-129[degree] and 17-n-octanoate: fine crystals with M.P. 117.5[degree]- 1180.