%0 Journal Article
%A Zhang, H.
%A Oppel, I.M.
%A Spiteller, M.
%A Guenther, K.
%A Boehmler, G.
%A Zuehlke, S.
%T Enantiomers of a Nonylphenol Isomer: Absolute Configurations and Estrogenic Potencies
%J Chirality
%V 21
%@ 0899-0042
%C New York, NY [u.a.]
%I Wiley Interscience
%M PreJuSER-1237
%P 271 - 275
%D 2009
%Z Contract grant sponsor: Ministry of Innovation, Science, Research and Technology of the State of North Rhine-Westphalia
%X 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.
%K Animals
%K Chromatography, High Pressure Liquid
%K Crystallography, X-Ray
%K Ecotoxicology
%K Estrogens: chemistry
%K Estrogens: isolation & purification
%K Estrogens: toxicity
%K Phenols: chemistry
%K Phenols: isolation & purification
%K Phenols: toxicity
%K Stereoisomerism
%K Estrogens (NLM Chemicals)
%K Phenols (NLM Chemicals)
%K nonylphenol (NLM Chemicals)
%K J (WoSType)
%F PUB:(DE-HGF)16
%9 Journal Article
%$ pmid:18553459
%U <Go to ISI:>//WOS:000262561200003
%R 10.1002/chir.20556
%U https://juser.fz-juelich.de/record/1237