Degradation of fenprostalene in aqueous solution.

The degradation of the prostaglandin fenprostalene (III) was studied in aqueous solution. The reaction was both specific acid and base catalyzed. The only reaction found to occur was hydrolysis of the methyl ester at C-1. Activation energies for the acid- and base-catalyzed reactions were determined and are nearly identical to that for the hydrolysis of ethyl acetate, a model ester. A competing acid-catalyzed reaction of the C-1 free acid of III was found to be approximately 10 times slower than the hydrolysis of III.