Über Androsteron. IV. Abbau des Stigmasterins zu Iso-Androsteron und Androstandion; die Verknüpfung des Corpus luteum-Hormons und allo-Pregnanolons mit Androsteron.

Abstract

The conversion of allo-pregnanolone, a tetra-hydro derivative of the corpus luteum hormone, to iso-androsterone and androsta-nedione shows that hormones of the [female] series can be converted to those of the [male] series in the laboratory. Stigmasterol can be used as starting material. Although androsterone differs from iso-androsterone only in the configuration of the hydroxyl group, it is 7 times as active. Just as the reduction of the carbonyl group in theelin to the secondary alcohol group increases the physiological activity 6 fold, so the reduction of androsterone to androstanediol by Na and alcohol increases the activity 3 fold. The product melts at 221[degree], [[alpha]]D23 12.6[degree], a di-acetyl derivative melting at 159-160[degree], [[alpha]]d23 12.5[degree], and showing the ester effect of prolonged action in physiological tests. The new substances have strong growth-promoting action on the seminal vesicles of rats.