Evaluating stereolability of target chiral chemical is pivotal when developing enantioselective studies. Ethofumesate-2-hydroxy is one of the main metabolites of ethofumesate, a chiral herbicide currently marketed as racemate. In order to perform enantioselective pharmacokinetic and metabolism studies, the stereolability of susceptible molecules should be evaluated. Based on that, dynamic high-performance liquid chromatography experiments were performed to evaluate ethofumesate-2-hydroxy enantiomerization process on-column. The thermodynamic results helped understand that ethofumesate-2-hydroxy enantiomerization is a bimolecular process assisted by acid and base catalysis. The enantiomerization barrier determined suggested that ethofumesate-2-hydroxy single enantiomers may undergo extensive racemization at ambient temperature turning ethofumesate-2-hydroxy enantioselective studies into an unfeasible task.
K E Y W O R D Sdynamic high-performance liquid chromatography, enantiomerization barrier determination, pesticides, stereolability Sep Sci plus 2018;1:771-775.