Enantiomers of a Nonylphenol Isomer: Absolute Configurations and Estrogenic Potencies

摘要

Enantiomers of 4-(1,1,2-trimethylliexyl)phenol, a chiral isomer of the endocrine disrupting chemical nonylphenol, have been resolved and isolated by preparative chiral HPLC. The absolute configurations of the enantiomers were glen determined by an X-ray crystallographic Study of the (-)-camplianoyl derivative of the First eluted enantiomer NP(35)E1. The first enantiomer (NP(35)E1) and the second enantiomer (NP(35)E2) eluted were found to have the S and R absolute configurations, respectively. The estrogenic potencies of the S and R enantiomers were tested by the E-screen assay. A slight difference was observed in the relative proliferative effect between the S enantiomer and R enantiomer in the E-screen assay. Chirality 21:271-275, 2009.