Recently, we found that direct photolysis of metabolites of trenbolone acetate, a trienone steroid extensively used as a growth promoter in animal agriculture, proceeds via photohydration, which most notably is reversible at ambient (pH 7, 25 C) conditions. This work presents a series of mechanistic investigations to probe rate-limiting reaction steps and transient intermediates during the reversible photohydration of TBA metabolites.  Further, in simulated diurnal cycling experiments, we extend the generality of this mechanism to other structurally analogous steroids in sunlit surface waters.  To date, our work suggests that the key moiety necessary for reversible photohydration is an enone functionality built into a larger conjugated pi-bond network within the steroid ring.  Such species represent a new class of environmental pollutant that undergoes unique, reversible phototransformation thereby promoting their persistence in surface waters.

Reversible photohydration of dienone and trienone steroids

246th National Meeting (2013)

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