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@ARTICLE{Boehme:12358,
      author       = {Boehme, R.M. and Andries, T. and Dötz, K.H. and Thiele, B.
                      and Guenther, K.},
      title        = {{S}ynthesis of defined endocrine-disrupting nonylphenol
                      isomers for biological and environmental studies},
      journal      = {Chemosphere},
      volume       = {80},
      issn         = {0045-6535},
      address      = {Amsterdam [u.a.]},
      publisher    = {Elsevier Science},
      reportid     = {PreJuSER-12358},
      pages        = {813 - 821},
      year         = {2010},
      note         = {Record converted from VDB: 12.11.2012},
      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.},
      keywords     = {Endocrine Disruptors: chemical synthesis / Endocrine
                      Disruptors: chemistry / Environmental Monitoring /
                      Environmental Pollutants: chemical synthesis / Environmental
                      Pollutants: chemistry / Isomerism / Molecular Structure /
                      Phenols: chemistry / Endocrine Disruptors (NLM Chemicals) /
                      Environmental Pollutants (NLM Chemicals) / Phenols (NLM
                      Chemicals) / nonylphenol (NLM Chemicals) / J (WoSType)},
      cin          = {IBG-2},
      ddc          = {333.7},
      cid          = {I:(DE-Juel1)IBG-2-20101118},
      pnm          = {Terrestrische Umwelt},
      pid          = {G:(DE-Juel1)FUEK407},
      shelfmark    = {Environmental Sciences},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:20452641},
      UT           = {WOS:000280688700020},
      doi          = {10.1016/j.chemosphere.2010.03.064},
      url          = {https://juser.fz-juelich.de/record/12358},
}