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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},
}