Isolierung von Dehydro-androsteron und anderen Oxyketonen aus Harn von trächtigen Stuten

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Abstract
The acids and phenols are removed from 20,000 1. of pregnant mares'' urine by treatment with alkali, the urine subjected to acid hydrolysis, and 4 kg. of neutral sirupy residue obtained. The residue is heated with 5 1. 90% alcohol containing 1 kg. KOBE 4 hrs. on the H2O bath, the mixture is poured into 50 1. water, extracted with benzene, the benzene soln. washed with 25% NaOH soln., concd., and 1.6 kg. of syrup containing a total of 6500 I.U. of activity according to the capon comb test obtained. The syrup is allowed to stand overnight in 6 1. 90% alcohol, the mixture filtered, the alcohol evaporated and 1.25 kg. neutral fraction obtained. The neutral fraction is refluxed with 3 1. benzene, 1 kg. pyridine and 750 g. phthalic an-hydride for 5 hrs., the mixture poured into water, and the soln. extracted with ether from which the esters are ex-tracted with Na2CO3 soln. and enough KOH added to give a conc. of 5%. The mixture is heated on the water bath 4 hrs. and extracted with ether, which is evaporated, and 676 g. of alcohols which contain a total of 5000 I.U. activity obtained. The 676 g. are warmed in 1.5 1. alcohol containing 150 g. acetic acid and 150 g. Girard reagent 45 min. and the mixture poured in 6 1. water containing 90 g. NaOH. The mixture is extracted with ether from which the hydroxy ketones are extracted with 10% alcohol soln. The ketone fraction weighs 65 g. and contains 3000 I.U. activity. The ketones are separated into 20 fractions by chromatographing on aluminum oxide. From these fractions the following compounds with their respective properties are obtained: 1. Allopregnanolon; m. 193[degree]-195[degree]; (a)D, + 80.3[degree] (acetate); forms an acetate (m. 147[degree]-148.5[degree]) and a benzoate (m. 202[degree]). 2. Hydroxy ketone, C19H30O2; m. 190.5[degree]-191[degree]; (a)D,[long dash]157[degree]; forms an acetate (m. 109[degree]-110[degree]) and a semi-carbazone (decomposes 282[degree]-285[degree]). 3. Substance A, C21H34O2-; m. 163[degree]-164[degree]; (a)D. +91.5[degree] (acetate); forms an acetate (m. 143[degree]-144[degree]) and a semi-carbazone of the acetate (decomposes 266[degree]-268[degree]). 4. Sub-stance B, C21H34O2; m. 196[degree]-197[degree]; (a)D, +93[degree]; forms a benzoate (m. 207[degree]-208[degree]) and a semicarbazone (decomposes 258][degree]-261[degree]). 5. Substance C, C19H30O2; m. 191[degree]-191.5[degree]; (a)D,[long dash]171[degree]; forms a benzoate (m. 215[degree]-216[degree]) and a semi-carbazone (decomposes 260[degree]-265[degree]). 6. Substance D; (a)D, + 40.2o (acetate); forms an acetate (m. 167[degree]) and a semi-carbazone of the acetate (decom. 261[degree]-264[degree]); has estrogenic activity. 7. Dehydroandrosterone, m. 149[degree]; forms an acetate (m. 171[degree]) and a benzoate (m. 251[degree]-253[degree]); has androgenic activity. Dehydroandrosterone shows the most activity in the capon comb test while substances A, B and C show slight activity.

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