TY  - JOUR
AU  - Boehme, R.M.
AU  - Andries, T.
AU  - Dötz, K.H.
AU  - Thiele, B.
AU  - Guenther, K.
TI  - Synthesis of defined endocrine-disrupting nonylphenol isomers for biological and environmental studies
JO  - Chemosphere
VL  - 80
SN  - 0045-6535
CY  - Amsterdam [u.a.]
PB  - Elsevier Science
M1  - PreJuSER-12358
SP  - 813 - 821
PY  - 2010
N1  - Record converted from VDB: 12.11.2012
AB  - 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.
KW  - Endocrine Disruptors: chemical synthesis
KW  - Endocrine Disruptors: chemistry
KW  - Environmental Monitoring
KW  - Environmental Pollutants: chemical synthesis
KW  - Environmental Pollutants: chemistry
KW  - Isomerism
KW  - Molecular Structure
KW  - Phenols: chemistry
KW  - Endocrine Disruptors (NLM Chemicals)
KW  - Environmental Pollutants (NLM Chemicals)
KW  - Phenols (NLM Chemicals)
KW  - nonylphenol (NLM Chemicals)
KW  - J (WoSType)
LB  - PUB:(DE-HGF)16
C6  - pmid:20452641
UR  - <Go to ISI:>//WOS:000280688700020
DO  - DOI:10.1016/j.chemosphere.2010.03.064
UR  - https://juser.fz-juelich.de/record/12358
ER  -