The widespread use of steroids by humans and livestock has raised concerns about their presence in the environment. Previous work has shown that some dienone and trienone steroids are expected to undergo reversible photohydration reactions in aquatic systems. In some environmental systems, these photohydration reactions may be affected by competing reactions with other reactive species. This study focuses on the photolysis and regeneration of the trienone steroid gestrinone in the presence of the nucleophile sodium azide. Previous work found direct photolysis of gestrinone occurs much faster at basic conditions (kobs = 0.300 s-1 at pH 9.00; kobs = 0.0157 s-1 at pH 5.00. Previous work also showed almost instantaneous regeneration of gestrinone in very acidic and very basic conditions. The rate of photolysis and regeneration of the gestrinone as well as its photoproduct distribution was examined in the presence of different concentrations of sodium azide at pH 5 and 9. Two main photoproducts are formed by direct photolysis at pH 5.00 and 9.00; in the presence of sodium azide an additional product is observed. The rate of photodegradation of gestrinone increases as the concentration of sodium azide increases at pH 5.00 while at pH 9.00 the concentration of sodium azide has little effect on the rate of photodegradation of gestrinone.

Aqueous photolysis of the steroid gestrinone in the presence of sodium azide

253rd National Meeting (2017)

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