Analytical and Bioanalytical Chemistry

, Volume 384, Issue 2, pp 542–546

Estrogen-active nonylphenols from an isomer-specific viewpoint: a systematic numbering system and future trends

Technical Note

DOI: 10.1007/s00216-005-0181-8

Cite this article as:
Guenther, K., Kleist, E. & Thiele, B. Anal Bioanal Chem (2006) 384: 542. doi:10.1007/s00216-005-0181-8
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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.

Supplementary material

216_2005_181_MOESM1_ESM.pdf (331 kb)
Supplementary material (PDF 331 kb)

Copyright information

© Springer-Verlag 2005

Authors and Affiliations

  1. 1.Research Centre JuelichInstitute for Chemistry and Dynamics of the Geosphere, Institute III: PhytosphereJuelichGermany