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Gas chromatography-mass spectrometry (GC-MS) with a 100 m capillary column at different oven temperatures is employed to separate isothermally p-nonylphenol into 21 isomers. Analysis of the resulting mass spectra of these isomers indicates that they could be classified into six groups with respect to different configurations of the alpha- and beta-C-atoms on the alkyl chains. Based on these basic structures nonylphenol isomers are synthesized and also characterized by GC-MS. The obtained data elucidate the complete structures of 10 nonylphenol isomers of the technical mixture. The most important features of the mass spectra and the 1H and 13C nuclear magnetic resonance (NMR) spectra of these isomers are presented.

4-Nonylphenols (NPs) are common products of biodegradation of a widely used group of nonionic surfactants, the nonylphenol ethoxylates (NPEs). These compounds are known to be persistent, toxic, and estrogen active. There is a worldwide scientific and public discussion on the potential consequences of human long term dietary exposure to such endocrine disrupters. Despite numerous determinations of NPs in environmental samples no systematical reports exist relating to concentrations of NPs in food. We analyzed NPs in 60 different foodstuff commercially available in Germany. The results indicate that NPs are ubiquitous in food. The concentrations of NPs on a fresh weight basis varied between 0.1 and 19.4 microg/kg regardless of the fat content of the foodstuff. Based on data on German food consumption rates and these first analyses of NPs in food, the daily intake for an adult was calculated to be 7.5 microg/day NPs. For infants exclusively fed with breast milk or infant formulas daily intakes of 0.2 microg/day and 1.4 microg/day NPs, respectively, can be estimated.