Enantiomers of a nonylphenol isomer: absolute configurations and estrogenic potencies.
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.
Zhang
Haifeng
H
Institute of Environmental Research (INFU), University of Dortmund, Dortmund, Germany.
Oppel
Iris M
IM
Spiteller
Michael
M
Guenther
Klaus
K
Boehmler
Gabriele
G
Zuehlke
Sebastian
S
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D054750:Ecotoxicology; D004967:Estrogens / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D013237:Stereoisomerism
D004967:Estrogens; D010636:Phenols; C025256:nonylphenol