Analysis of Reaction Products of Food Contaminants and Ingredients: Bisphenol A Diglycidyl Ether (BADGE) in Canned Foods

Abstract

Bisphenol A diglycidyl ether (BADGE) is an epoxide that is used as a starting substance in the manufacture of can coatings for food-contact applications. Following migration from the can coating into food, BADGE levels decay and new reaction products are formed by reaction with food ingredients. The significant decay of BADGE was demonstrated by liquid chromatographic (LC) analysis of foodstuffs, that is, tuna, apple puree, and beer, spiked with BADGE before processing and storage. Life-science inspired analytical approaches were successfully applied to study the reactions of BADGE with food ingredients, for example, amino acids and sugars. An improved mass balance of BADGE was achieved by selective detection of reaction products of BADGE with low molecular weight food components, using a successful combination of stable isotopes of BADGE and analysis by LC coupled to fluorescence detection (FLD) and high-resolution mass spectrometric (MS) detection. Furthermore, proteomics approaches showed that BADGE also reacts with peptides (from protein digests in model systems) and with proteins in foods. The predominant reaction center for amino acids, peptides, and proteins was cysteine.

Widespread Occurrence and Distribution of Bisphenol A Diglycidyl Ether (BADGE) and its Derivatives in Human Urine from the United States and China

“…15,16,19,20 However, it is believed that BPA in canned food is released primarily from BADGE-based epoxy resin coating. 21 Although the occurrence of BADGEs in foodstuffs has been reported, [3][4][5][6]22 human biomonitoring studies, which report concentrations in body tissues or fluids, are still lacking. Moreover, the forms and compositions of BADGE can change in human bodies through the formation of conjugated metabolites (e.g., glucuronidation and/or sulfation) or as hydrolytic and hydrochloro derivatives by the action of epoxide hydrolase.…”

Determination of bisphenol A diglycidyl ether, novolac glycidyl ether and their derivatives migrated from can coatings into foodstuff by UPLC-MS/MS

“…BADGE and NOGE can migrate from the lacquers into canned food content, and they even can react with some food ingredients [5,6]. The major reaction of BADGE and BFDGE (the main representative of NOGE) with food ingredients is hydrolytic opening of the epoxy rings, which yield BADGEÁH 2 O, BADGEÁ2H 2 O, BFDGEÁH 2 O and BFDGEÁ2H 2 O [7].…”

Food packaging and migration of food contact materials: will epidemiologists rise to the neotoxic challenge?

“…Improvements in analytical chemistry have led to the constant reduction of detection limits, thereby disclosing the migration of NIAS into food 7 32 33…”