Estrogen-active nonylphenols from an isomer-specific viewpoint: a systematic numbering system and future trends |
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Authors: | Klaus Guenther Einhard Kleist Bjoern Thiele |
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Institution: | (1) Research Centre Juelich, Institute for Chemistry and Dynamics of the Geosphere, Institute III: Phytosphere, 52425 Juelich, Germany |
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Abstract: | 4-Nonylphenols (NPs) are very important environmentally relevant substances. They are persistent, toxic, endocrine-disrupting
chemicals that are priority hazardous substances of the EU Water Framework Directive. NPs are degradation products of 4-nonylphenol
ethoxylates (NPEs), a widely used group of nonionic surfactants. The technical synthesis of NP leads to a complex mixture
of NPs consisting of isomeric compounds that have different branched nonyl side chains. It has recently become clear that
an isomer-specific view is absolutely necessary when it comes to correctly evaluating the biological effects of NPs and their
behavior in the environment, including degradation processes. To rationalize the identification of individual NP isomers in
scientific studies, we have developed a numbering system for all possible NP isomers that follows the IUPAC rules of substituent
characterization in alkylphenols. The 211 possible constitutional isomers of NP are numbered according to a hierarchical and
logical system. In the future, multidimensional coupling systems—for example GC×GC-TOF-MS—will be needed to study these highly
complex class of substances.
Electronic Supplementary Material Supplementary material is available for this article at |
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