%0 Journal Article
%A Boehme, R.M.
%A Andries, T.
%A Dötz, K.H.
%A Thiele, B.
%A Guenther, K.
%T Synthesis of defined endocrine-disrupting nonylphenol isomers for biological and environmental studies
%J Chemosphere
%V 80
%@ 0045-6535
%C Amsterdam [u.a.]
%I Elsevier Science
%M PreJuSER-12358
%P 813 - 821
%D 2010
%Z Record converted from VDB: 12.11.2012
%X Nonylphenols are very important environmentally relevant substances in the focus of the world-wide endocrine disrupter research for over 25 years. Thus, they are among the 10 priority hazardous substances of the new European Union Water Framework Directive. They consist of a very complex mixture of isomers representing therefore a multi-component problem like dioxins or PCBs. As estrogenic effect and degradation behavior in the environment of individual 4-nonylphenols are heavily dependent on the structure and bulkiness of the side chain, it is absolutely necessary to consider the nonylphenol problem from an isomer-specific viewpoint. Therefore a range of 28 differently branched nonylphenol isomers were synthesized for biological and environmental studies. Nonylphenols with a quaternary alpha-carbon, like 4-(1,1,3,4-tetramethylpentyl)phenol (4-NP(95)) and 4-(1-ethyl-1,3,3-trimethylbutyl)phenol (4-NP(170)), were obtained by Friedel-Crafts alkylation of anisole with tertiary nonyl bromides and demethylation with BI(3). Nonylphenols with a tertiary alpha-carbon, such as 4-(1,2-dimethylheptyl)phenol (4-NP(10)) and 4-(1,2,4-trimethylhexyl)phenol (4-NP(41)), were accessible via coupling of p-methoxyphenylmagnesium bromide with ketones. Nonylphenols bearing a quaternary beta-carbon, like 4-(2,2-dimethylheptyl)phenol (4-NP(15)) and 4-(1,2,2-trimethylhexyl)phenol (4-NP(39)), were synthesized starting from 4'-methoxyisobutyrophenone. The compounds were characterized by GC-MS and NMR-spectroscopy. The individual isomers were designated according to the Juelich Nomenclature.
%K Endocrine Disruptors: chemical synthesis
%K Endocrine Disruptors: chemistry
%K Environmental Monitoring
%K Environmental Pollutants: chemical synthesis
%K Environmental Pollutants: chemistry
%K Isomerism
%K Molecular Structure
%K Phenols: chemistry
%K Endocrine Disruptors (NLM Chemicals)
%K Environmental Pollutants (NLM Chemicals)
%K Phenols (NLM Chemicals)
%K nonylphenol (NLM Chemicals)
%K J (WoSType)
%F PUB:(DE-HGF)16
%9 Journal Article
%$ pmid:20452641
%U <Go to ISI:>//WOS:000280688700020
%R 10.1016/j.chemosphere.2010.03.064
%U https://juser.fz-juelich.de/record/12358