Journal Article

PreJuSER-1237

http://join2-wiki.gsi.de/foswiki/pub/Main/Artwork/join2_logo100x88.png Enantiomers of a Nonylphenol Isomer: Absolute Configurations and Estrogenic Potencies

Zhang, H. ; Oppel, I. M. ; Spiteller, M. ; Guenther, K.FZJ* ; Boehmler, G. ; Zuehlke, S.

2009
Wiley Interscience New York, NY [u.a.]

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Please use a persistent id in citations: doi:10.1002/chir.20556

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.

Keyword(s): Animals (MeSH) ; Chromatography, High Pressure Liquid (MeSH) ; Crystallography, X-Ray (MeSH) ; Ecotoxicology (MeSH) ; Estrogens: chemistry (MeSH) ; Estrogens: isolation & purification (MeSH) ; Estrogens: toxicity (MeSH) ; Phenols: chemistry (MeSH) ; Phenols: isolation & purification (MeSH) ; Phenols: toxicity (MeSH) ; Stereoisomerism (MeSH) ; Estrogens ; Phenols ; nonylphenol ; J ; endocrine disrupting chemicals (auto) ; X-ray crystallography (auto) ; E-screen assay (auto)

Note: Contract grant sponsor: Ministry of Innovation, Science, Research and Technology of the State of North Rhine-Westphalia

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Research Program(s):

1. Terrestrische Umwelt (P24)

Appears in the scientific report 2009

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