Enantiomers of a nonylphenol isomer: Absolute configurations and estrogenic potencies

Enantiomers of 41,1,2trimethylhexylphenol, 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 then determined by an Xray crystallographic study of the −camphanoyl derivative of the first eluted enantiomer NP35E1. The first enantiomer NP35E1 and the second enantiomer NP35E2 eluted were found to have the Sand Rabsolute configurations, respectively. The estrogenic potencies of the Sand Renantiomers were tested by the Escreen assay. A slight difference was observed in the relative proliferative effect between the Senantiomer and Renantiomer in the Escreen assay. Chirality, 2009. © 2008 WileyLiss, Inc.