Synthesis and Kinetic Studies of a Simple Prostacyclin Model

Article abstract of DOI:10.1021/jo00229a004

A simple prostacyclin model, (Z)-6,9-epoxynon-5-enoic acid, has been synthesized, and the rate of hydrolysis of the vinyl ether functional group of it and its methyl ester has been measured by monitoring UV spectral changes over the pH range 1-8 at 25.0 +/- 0.1 deg C and total ionic strength 0.1 M.The measurements show that (Z)-6,9-epoxynon-5-enoic acid is 82 times more reactive than its methyl ester at high pH when the carboxylic acid group is in an ionized form.The present results indicate that the simple model closely mimics the behavior of prostacyclin.