title: Instability of an aromatic amine in fatty food and fatty food simulant: characterisation of reaction products and prediction of their toxicity.
abstract: It is a well-known fact that amines are not stable in food of a fatty nature. In this study the synthesis and characterisation of the products obtained as a result of the reaction of amines in a fatty medium are reported. Based on the well-known reactions among amines and acid and esters groups, two novel compounds were synthesised using m-xylylenediamine (mXDA), a primary diamine widely used as monomer in the manufacture of food contact materials and two fatty acids, oleic acid and palmitic acid, which occur in most fats. The resulting compounds were two molecules belonging to the family of fatty acid amides, dioleamide and dipalmitamide. A complete characterisation of both products was carried out employing several techniques such as infrared spectroscopy, (1)H- and (13)C-NMR spectroscopy, electron ionisation mass spectrometry, LC-MS/MS and UV spectrometry. The results obtained by the different techniques were well correlated. In the second part of the work, the formation of these compounds in real samples was evaluated. For this purpose a certain volume of olive oil was spiked with a known amount of mXDA. Olive oil was selected as a fatty medium since it is a widely consumed food and additionally is used as a fatty food simulant in migration studies of food contact materials. A method was developed to extract the fatty acid amides from the fatty matrix, which were then identified by LC-MS/MS. The toxicity of the synthesised compounds was predicted using a toxicity estimation software tool.
authors.affiliation: a Department of Analytical Chemistry, Nutrition and Food Science. Faculty of Pharmacy , University of Santiago de Compostela , Santiago de Compostela , Spain.
authors.forename: R
authors.initials: R
authors.lastname: Paseiro-Cerrato
authors.forename: A
authors.initials: A
authors.lastname: Rodríguez-Bernaldo de Quirós
authors.forename: R
authors.initials: R
authors.lastname: Sendón
authors.forename: J
authors.initials: J
authors.lastname: Bustos
authors.forename: J J
authors.initials: JJ
authors.lastname: Sánchez
authors.forename: J
authors.initials: J
authors.lastname: López-Hernández
authors.forename: P
authors.initials: P
authors.lastname: Paseiro-Losada
mesh_terms: D000577:Amides / Q000032:analysis / Q000138:chemical synthesis*; D002853:Chromatography, Liquid; D004058:Diffusion; D005506:Food Contamination; D018857:Food Packaging; D006801:Humans; D008956:Models, Chemical; D019301:Oleic Acid / Q000737:chemistry*; D000069463:Olive Oil; D019308:Palmitic Acid / Q000737:chemistry*; D010938:Plant Oils / Q000737:chemistry; D053719:Tandem Mass Spectrometry; D014992:Xylenes / Q000737:chemistry*
chemical_list: D000577:Amides; D000069463:Olive Oil; D010938:Plant Oils; D014992:Xylenes; C066883:1,3-xylenediamine; D019301:Oleic Acid; D019308:Palmitic Acid
keywords: amines; fatty acid amides characterisation; fatty food; food contact materials; m-xylylenediamine; olive oil