Fellbach, Germany
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Buhrke T.,German Federal Institute for Risk Assessment | Weihaar R.,CVUA Stuttgart | Lampen A.,German Federal Institute for Risk Assessment
Archives of Toxicology | Year: 2011

3-Chloro-1,2-propanediol (3-MCPD) fatty acid esters are formed upon thermal processing of fat-containing foods in the presence of chloride ions. Upon hydrolytic cleavage, these substances could release free 3-MCPD. This compound is toxicologically well characterised and displayed cancerogenic potential in rodent models. Recently, serious contaminations of different food products with 3-MCPD fatty acid esters have been reported. In regard to a risk assessment, the key question is to which degree these 3-MCPD fatty acid esters are hydrolysed in the human gut. Therefore, the aim of the present project was to examine the hydrolysis of 3-MCPD fatty acid esters and the resulting release of free 3-MCPD by using differentiated Caco-2 cells, a cellular in vitro model for the human intestinal barrier. Here, we show that 3-MCPD fatty acid esters at a concentration of 100 μM were neither absorbed by the cells nor the esters were transported via a Caco-2 monolayer. 3-MCPD-1-monoesters were hydrolysed in the presence of Caco-2 cells. In contrast, a 3-MCPD-1,2-diester used in this study was obviously absorbed and metabolised by the cells. Free 3-MCPD was not absorbed by the cells, but the substance migrated through a Caco-2 monolayer by paracellular diffusion. From these in vitro studies, we conclude that 3-MCPD-1-monoesters are likely to be hydrolysed in the human intestine, thereby increasing the burden with free 3-MCPD. In contrast, intestinal cells seem to have the capacity to metabolise 3-MCPD diesters, thereby detoxifying the 3-MCPD moiety. © 2011 Springer-Verlag.

Weisshaar R.,CVUA Stuttgart
European Journal of Lipid Science and Technology | Year: 2011

Many studies and surveys concerning the ocurrence and exposure of free 3-MCPD have been performed in the last 30years. Although a huge number of food samples, especially fats and oils, were analysed in the last 3years, no systematic study about ester-bound 3-MCPD and the resulting exposure was performed up to now. In this paper published data of 3-MCPD esters in different foods are reviewed, with a focus on fats and oils and infant formula. Concerning fats and oils, only in refined products significant concentrations of 3-MCPD esters in a range from 0.25-15mg/kg were present, with the highest levels found in palm oil. In infant formula, levels of ester-linked 3-MCPD were nearly unchanged in three surveys from April 2009 to May 2010, while levels of ester-linked glycidol decreased dramatically in this period. Based on analytical data of more than 200 refined fats and oils, an average daily intake of 1.5μg 3-MCPD/kg bw/day, respectively, 0.9μg glycidol/kg bw/day was calculated to result from consumer exposure to ester-bound 3-MCPD and glycidol. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Jung T.,CVUA Stuttgart | Jung T.,TU Dresden | Simat T.J.,TU Dresden | Altkofer W.,CVUA Stuttgart | Fugel D.,CVUA Stuttgart
Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment | Year: 2013

In a surveillance study from 2008 to 2011, in total 310 food products, predominately packed in cartonboard, were collected from the German market. First, the packaging materials were analysed for their content of six photo-initiators and five amine synergists by high-performance liquid chromatography with diode array detection (HPLC-DAD). If high amounts of these substances were detected, subsequently the foodstuffs were analysed by means of HPLC-MS or tandem MS, respectively. Benzophenone (BP) was detected in 49% of the packaging materials and was thus the most often determined compound, followed by 4-methylbenzophenone (MBP, 8%), 1-hydroxy-cyclohexylphenylketone (HCHPK, 7%) and methyl-o-benzoylbenzoate (MOBB, 5%). In total, 99 foodstuffs were analysed and in 20 cases one or more photo-initiators and/or amine synergists were detected in quantities above the legally acceptable limits in food. This resulted in several notifications in the European Rapid Alert System for Food and Feed (RASFF); the best known is MBP in breakfast cereals. Contamination of the foodstuff by the photo-initiators and/or amine synergists also occurred when it was in indirect contact with the printed packaging material and no adequate barrier material was used to prevent migration. The data also clearly demonstrate that polyethylene films are not suitable to inhibit migration. Storage of samples until the best before date showed that HCHPK, BP and MBP migrate very easily via the gas phase. In contrast, 4-phenylbenzophenone and 4,4′-bis(diethylamino)benzophenone migrated only very slowly or, respectively, not in quantifiable amounts into the foodstuffs. Differences in transfer rates for HCHPK, BP and MBP from several packagings into food and Tenax®, respectively, lead to the assumption that both the food matrix as well as the extent of cross-linking of the printing ink during curing may have an influence on the level of migration. © 2013 Taylor & Francis.

Jung T.,CVUA Stuttgart | Simat T.J.,TU Dresden | Altkofer W.,CVUA Stuttgart
Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment | Year: 2010

The case of isopropylthioxanthone (ITX) showed conclusively that the ingredients of ultraviolet printing inks may migrate into packaged foodstuffs. For multilayered materials like beverage cartons, the only way that mass transfer can occur is by the so-called set-off effect. In contrast, in the case of rigid plastics like yoghurt cups, two other methods of mass transfer, permeation and gas phase, have to be considered. In cooperation with producers of ink, plastic cups and yoghurt, a project was conducted in order to elucidate the mass transfer of ink ingredients. In addition, the influence of storage time and the age of ultraviolet lamps on the migration level was examined. The suitability of 50% ethanol as a simulant for yoghurt was also tested. ITX was chosen as a model migrant, as it is easily detectable. Furthermore, the migration of two other substances, the photo-initiator 2-methyl-4′-(methylthio)-2-morpholinopropiophenone (MTMP) and the amine synergist ethyl-4-(dimethylamino)benzoate (EDAB), which may be used in combination with ITX, was studied. Before being filled with yoghurt or 50% ethanol, the printed cups were stored under different contact conditions, with and without contact between the inner layer and the printed surfaces, in order to distinguish between the possible mass transfer ways. All analyses were performed by means of high performance liquid chromatography with diode array and fluorescence detection (HPLC-DAD/FLD). It was shown that contamination with ITX and EDAB occurs via set-off and that the degree of migration increases with lamp age and storage time of the unfilled cups. Migration of MTMP was not detectable. The results show that besides the careful selection of the appropriate raw materials for printing ink, a close monitoring of the process also plays a major role in migration control. In addition, the results proved that 50% ethanol is a suitable simulant for yoghurt. © 2010 Taylor & Francis.

Jung T.,CVUA Stuttgart | Jung T.,TU Dresden | Browatzki C.,CVUA Stuttgart | Browatzki C.,TU Dresden | Simat T.J.,TU Dresden
Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment | Year: 2014

The objective of this work was to develop a HPLC-DAD method suitable for the screening of food contact materials for a total of 63 monomeric and polymeric photoinitiators and amine synergists. Such multi-analyte methods are worthwhile for official control laboratories, where normally no information about the composition of the applied inks or varnishes on the printed or lacquered materials is available and thus target analyses are not feasible. The polymeric analytes were each separated in a multitude of substance peaks, which largely overlaid those of the other compounds. Thus, for 13 polymeric photoinitiators and amine synergists a hydrolysis method was developed that reduced the number of ultraviolet (UV) detectable peaks to only one. This allowed easier identification and - preliminary - semi-quantification of these polymeric substances with adequate limits of detection. The remaining 50 photoinitiators and amine synergists were combined in one HPLC-DAD method. But since many of these substances are structurally related, partly retention times and spectra did not differ significantly. Thus selectivity was enhanced by preparing a database containing all spectra and retention times of the investigated compounds. Furthermore, the retention times of those 50 substances were calculated relative to two internal standards to overcome variances of retention from run to run or due to matrix effects. The developed method was tested for the analysis of food contact materials. Extractions of these were performed with acetonitrile and partially the extracts were subsequently concentrated in a steam of nitrogen. Limits of detection of photoinitiators and amine synergists in concentrated packaging extracts were in the range between 0.02 and 5.5 μg dm-2. © 2014 Taylor & Francis.

Jung T.,CVUA Stuttgart | Jung T.,TU Dresden | Simat T.J.,TU Dresden
Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment | Year: 2014

The aim of this investigation was to develop a multi-analyte method for the analysis of a total of 53 photoinitiators and amine synergists in food contact materials and foodstuffs. As for many of these compounds a maximum LOD of 10 μg kg-1 food applies, a sensitive and selective detection method is needed to control at these limits. Here an UHPLC-MS/MS was chosen to achieve this object. In the end 49 compounds could be integrated into one analytical method. This is nearly twice as many compared with other by now available methods. Only 11.5 min are needed for the analysis of one sample, allowing a high sample throughput. The LODs, which were determined in acetonitrile in the absence of matrix interferences, are sufficient to control at the legally acceptable limits, except for five photoinitiators. The developed method was tested for the analysis of food contact materials and foodstuffs. In the latter case a muesli matrix was spiked at four different concentration levels to determine the recovery rates. Extractions were performed in each case with acetonitrile. For 87% of the photoinitiators and amine synergists recoveries from the muesli were in the range between 70% and 120%. Thus, a comprehensive detection method for the analysis of food contact materials and foodstuffs for these potential migrating substances is now available, allowing the safe identification and control of migration levels in foodstuffs for the majority of the tested compounds. In particular, this multi-analyte method is worthwhile for official control laboratories where normally no information about the composition of applied inks on the food contact materials is available and thus target analyses are not feasible. © 2014 Taylor & Francis.

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