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| Home > Publications database > Synthesis of defined endocrine-disrupting nonylphenol isomers for biological and environmental studies |
| Journal Article | PreJuSER-12358 |
; ; ; ;
2010
Elsevier Science
Amsterdam [u.a.]
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Please use a persistent id in citations: doi:10.1016/j.chemosphere.2010.03.064
Abstract: 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.
Keyword(s): Endocrine Disruptors: chemical synthesis (MeSH) ; Endocrine Disruptors: chemistry (MeSH) ; Environmental Monitoring (MeSH) ; Environmental Pollutants: chemical synthesis (MeSH) ; Environmental Pollutants: chemistry (MeSH) ; Isomerism (MeSH) ; Molecular Structure (MeSH) ; Phenols: chemistry (MeSH) ; Endocrine Disruptors ; Environmental Pollutants ; Phenols ; nonylphenol ; J ; Nonylphenol synthesis (auto) ; Grignard reaction (auto) ; Friedel-Crafts alkylation (auto) ; Quaternary nonylphenol isomers (auto) ; Tertiary nonylphenol isomers (auto) ; Isomer design (auto)
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