Über Glykoside der Oestronreihe

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Abstract
Estronetetraacetylglucoside was prepared by dissolving 8.1 g. of estrone and 12.3 g. of aceto-bromoglucose in 500 cc. of acetone, and adding 15 cc. of 2 N KOH in 100 cc. of acetone. After standing 12 hrs., the acetone was removed in vacuo, and the residue dissolved in C6H6. By washing the C6H6 with dilute alkali, 74.2% of the estrone was recovered. Upon evaporation of the C6H6 soln., estronetetraacetylglucoside in 10% yield was obtained, which, when recrystallized from alcohol, melted at 214[degree]. The compound was also prepared in 60% yield by dissolving 8 g. of estrone and 20 g. of acetobromoglucose in 50 cc. of quinoline, and adding Ag2CO3. After heating, 250 cc. of acetic acid were added, and the mixture extracted with C6H6 as before. Estradiolglucoside, m. 234[degree], was prepd. by hydro-genation of estronetetraacetylglucoside. In divided doses, estroneglucoside was 5 times as active in the castrated mouse, and 0.5 times as active in the castrated rat, as estrone. In a single dose, it was about twice as active as estrone in the rat. Estronetetraacetylglucoside was less active than estroneglucoside. In divided doses, estradiolglucoside was about 1/6 as active as estradiol on the mouse, and as active as estradiol on the rat. In a single dose in the rat, it was 5 times as active as estradiol. The glucosides of the estrone series may be of use in medicine.

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