TY  - JOUR
AU  - Zhang, H.
AU  - Oppel, I.M.
AU  - Spiteller, M.
AU  - Guenther, K.
AU  - Boehmler, G.
AU  - Zuehlke, S.
TI  - Enantiomers of a Nonylphenol Isomer: Absolute Configurations and Estrogenic Potencies
JO  - Chirality
VL  - 21
SN  - 0899-0042
CY  - New York, NY [u.a.]
PB  - Wiley Interscience
M1  - PreJuSER-1237
SP  - 271 - 275
PY  - 2009
N1  - Contract grant sponsor: Ministry of Innovation, Science, Research and Technology of the State of North Rhine-Westphalia
AB  - 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.
KW  - Animals
KW  - Chromatography, High Pressure Liquid
KW  - Crystallography, X-Ray
KW  - Ecotoxicology
KW  - Estrogens: chemistry
KW  - Estrogens: isolation & purification
KW  - Estrogens: toxicity
KW  - Phenols: chemistry
KW  - Phenols: isolation & purification
KW  - Phenols: toxicity
KW  - Stereoisomerism
KW  - Estrogens (NLM Chemicals)
KW  - Phenols (NLM Chemicals)
KW  - nonylphenol (NLM Chemicals)
KW  - J (WoSType)
LB  - PUB:(DE-HGF)16
C6  - pmid:18553459
UR  - <Go to ISI:>//WOS:000262561200003
DO  - DOI:10.1002/chir.20556
UR  - https://juser.fz-juelich.de/record/1237
ER  -