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000012358 0247_ $$2pmid$$apmid:20452641
000012358 0247_ $$2DOI$$a10.1016/j.chemosphere.2010.03.064
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000012358 084__ $$2WoS$$aEnvironmental Sciences
000012358 1001_ $$0P:(DE-HGF)0$$aBoehme, R.M.$$b0
000012358 245__ $$aSynthesis of defined endocrine-disrupting nonylphenol isomers for biological and environmental studies
000012358 260__ $$aAmsterdam [u.a.]$$bElsevier Science$$c2010
000012358 300__ $$a813 - 821
000012358 3367_ $$0PUB:(DE-HGF)16$$2PUB:(DE-HGF)$$aJournal Article
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000012358 440_0 $$01228$$aChemosphere$$v80$$x0045-6535$$y7
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000012358 520__ $$aNonylphenols are very important environmentally relevant substances in the focus of the world-wide endocrine disrupter research for over 25 years. Thus, they are among the 10 priority hazardous substances of the new European Union Water Framework Directive. They consist of a very complex mixture of isomers representing therefore a multi-component problem like dioxins or PCBs. As estrogenic effect and degradation behavior in the environment of individual 4-nonylphenols are heavily dependent on the structure and bulkiness of the side chain, it is absolutely necessary to consider the nonylphenol problem from an isomer-specific viewpoint. Therefore a range of 28 differently branched nonylphenol isomers were synthesized for biological and environmental studies. Nonylphenols with a quaternary alpha-carbon, like 4-(1,1,3,4-tetramethylpentyl)phenol (4-NP(95)) and 4-(1-ethyl-1,3,3-trimethylbutyl)phenol (4-NP(170)), were obtained by Friedel-Crafts alkylation of anisole with tertiary nonyl bromides and demethylation with BI(3). Nonylphenols with a tertiary alpha-carbon, such as 4-(1,2-dimethylheptyl)phenol (4-NP(10)) and 4-(1,2,4-trimethylhexyl)phenol (4-NP(41)), were accessible via coupling of p-methoxyphenylmagnesium bromide with ketones. Nonylphenols bearing a quaternary beta-carbon, like 4-(2,2-dimethylheptyl)phenol (4-NP(15)) and 4-(1,2,2-trimethylhexyl)phenol (4-NP(39)), were synthesized starting from 4'-methoxyisobutyrophenone. The compounds were characterized by GC-MS and NMR-spectroscopy. The individual isomers were designated according to the Juelich Nomenclature.
000012358 536__ $$0G:(DE-Juel1)FUEK407$$2G:(DE-HGF)$$aTerrestrische Umwelt$$cP24$$x0
000012358 588__ $$aDataset connected to Web of Science, Pubmed
000012358 650_2 $$2MeSH$$aEndocrine Disruptors: chemical synthesis
000012358 650_2 $$2MeSH$$aEndocrine Disruptors: chemistry
000012358 650_2 $$2MeSH$$aEnvironmental Monitoring
000012358 650_2 $$2MeSH$$aEnvironmental Pollutants: chemical synthesis
000012358 650_2 $$2MeSH$$aEnvironmental Pollutants: chemistry
000012358 650_2 $$2MeSH$$aIsomerism
000012358 650_2 $$2MeSH$$aMolecular Structure
000012358 650_2 $$2MeSH$$aPhenols: chemistry
000012358 650_7 $$00$$2NLM Chemicals$$aEndocrine Disruptors
000012358 650_7 $$00$$2NLM Chemicals$$aEnvironmental Pollutants
000012358 650_7 $$00$$2NLM Chemicals$$aPhenols
000012358 650_7 $$025154-52-3$$2NLM Chemicals$$anonylphenol
000012358 650_7 $$2WoSType$$aJ
000012358 65320 $$2Author$$aNonylphenol synthesis
000012358 65320 $$2Author$$aGrignard reaction
000012358 65320 $$2Author$$aFriedel-Crafts alkylation
000012358 65320 $$2Author$$aQuaternary nonylphenol isomers
000012358 65320 $$2Author$$aTertiary nonylphenol isomers
000012358 65320 $$2Author$$aIsomer design
000012358 7001_ $$0P:(DE-HGF)0$$aAndries, T.$$b1
000012358 7001_ $$0P:(DE-HGF)0$$aDötz, K.H.$$b2
000012358 7001_ $$0P:(DE-Juel1)129410$$aThiele, B.$$b3$$uFZJ
000012358 7001_ $$0P:(DE-Juel1)VDB40956$$aGuenther, K.$$b4$$uFZJ
000012358 773__ $$0PERI:(DE-600)1496851-4$$a10.1016/j.chemosphere.2010.03.064$$gVol. 80, p. 813 - 821$$p813 - 821$$q80<813 - 821$$tChemosphere$$v80$$x0045-6535$$y2010
000012358 8567_ $$uhttp://dx.doi.org/10.1016/j.chemosphere.2010.03.064
000012358 8564_ $$uhttps://juser.fz-juelich.de/record/12358/files/FZJ-12358.pdf$$yRestricted$$zPublished final document.
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