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6. Enantiomers of a nonylphenol isomer: absolute configurations and estrogenic potencies.

Author

Zhang H, Oppel IM, Spiteller M, Guenther K, Boehmler G, and Zuehlke S

Subjects
Animals, Chromatography, High Pressure Liquid, Crystallography, X-Ray, Ecotoxicology, Estrogens isolation & purification, Phenols isolation & purification, Stereoisomerism, Estrogens chemistry, Estrogens toxicity, Phenols chemistry, Phenols toxicity
Abstract

Enantiomers of 4-(1,1,2-trimethylhexyl)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 then determined by an X-ray crystallographic study of the (-)-camphanoyl 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., ((c) 2008 Wiley-Liss, Inc.)

Published
2009
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