Migration of bisphenol-A diglycidyl ether (BADGE) and its reaction products in canned foods

Bisphenol-A diglycidyl ether (BADGE) is used as an additive or starting agent in coatings for cans. The presence of hydrochloric acid in the organosol (PVC-based) lacquers results in formation of chlorohydroxy compounds of BADGE. These compounds, as well as BADGE itself, are potential migrants into the preserved food and are of toxicological concern. In the present investigation the presence of BADGE and the chlorohydroxy compounds (BADGE.HCl and BADGE.2HCl) in various kinds of canned foods from 30 brands have been determined by HPLC with fluorescence detection. BADGE was found in levels up to 5.1mg/kg in the food and only in food from cans containing BADGE.HCl and BADGE.2HCl in the lacquers. BADGE was found both in fish in oil and in fish in tomato sauce, however, the highest amounts were found in the fatty foodstuffs. BADGE.HCl and BADGE.2HCl were found in concentrations up to 2.4mg/kg and 8.3mg/kg, respectively. Unlike BADGE, BADGE.2HCl was found in similar concentrations in fish in oil and in fish in tomato sauce. In aqueous and acidic foodstuffs BADGE readily hydrolyses into mono- and dihydrolysed products (BADGE.H₂O and BADGE.2H₂O). In this study BADGE.H₂O was not found in any food sample, whereas BADGE.2H₂O was found in levels up to 2.6mg/kg. The Scientific Committee for Food (SCF) of the European Commission has proposed that a limit of restriction of 1mg/kg food shall include BADGE itself and BADGE.H₂O, BADGE.HCl, BADGE.2HCl and BADGE.HCL.H₂O. The present results indicate that the migration of BADGE.HCl and BADGE.2HCl, compounds with almost no data on toxicity, implies a greater problem than BADGE.H₂O and BADGE.2H₂O.     

Survey of bisphenol a diglycidyl ether (BADGE) in canned foods.

2,2-Bis(4-hydroxyphenyl)propane bis(2,3-epoxypropyl) ether (BADGE) is used in the manufacture of lacquers for coating the inside of food and beverage cans. In June 1996 the EC Scientific Committee for Food temporarily increased the specific migration limit applying to BADGE to 1 mg/kg pending consideration of additional toxicological data. In order to find out if there is migration of BADGE from can coatings into foods, a 'worst case' sampling exercise has been conducted to survey those canned foods where the propensity for migration of BADGE was judged to be highest. The foods surveyed include canned fish in oil, meat and milk and, altogether, BADGE was determined in 181 retail samples. Analysis for BADGE was conducted, in duplicate, by HPLC with fluorescence detection with confirmation of BADGE identity by GC/MS analysis using selected ion monitoring. BADGE was found at levels exceeding 1 mg/kg in seven of the 15 canned anchovy samples and five of the 22 sardine samples purchased during the period September 1995-July 1996. Infrared analysis of the can coatings provided strong evidence that the higher BADGE levels found were associated with use of PVC organosol lacquers, although in some cases cans coated with organosols gave low BADGE results. For canned sardine samples found to contain greater than 0.5 mg/kg BADGE in the total contents, a replicate can was opened and separate analyses performed on the drained fish and the oil. The results clearly showed that BADGE concentrations in the oil were about 20 times higher than in the drained fish. Further samples of canned sardines and anchovies were purchased in June/July 1997 and, in all cases, BADGE levels were found to be below 1 mg/kg. In the other retail canned foods, BADGE was not detectable (DL = 0.02 mg/kg) or detected at concentrations well below the temporary SML of 1 mg/kg.     

Simultaneous determination of bisphenol A-diglycidyl ether, bisphenol F-diglycidyl ether and their hydrolysis and chlorohydroxy derivatives in canned foods

A new method for the simultaneous determination of bisphenol A-diglycidyl ether (BADGE), bisphenol F-diglycidyl ether (BFDGE) and their hydrolysis and chlorohydroxy derivatives in canned foods is presented. Oily and aqueous food samples were extracted with tert-butyl methyl ether and acetonitrile, respectively. The compounds in both extracts were determined by using reverse-phase gradient high-performance liquid chromatography with fluorescence detection. Optimization of extraction and chromatographic determination is outlined in detail. After validation the method was used to analyze various canned food samples, such as tuna and sardine in oil, vegetables, fruit cocktails, etc. In none of the samples were significant amounts ( >100 μg/kg) of BADGE or BFDGE found, whereas in most samples BADGE/BFDGE chlorohydroxy compounds were detected. These originate most probably from the use of organosol varnishes instead of epoxy resins. Risk assessment and regulations of these compounds by the European Union are urgently needed. Additionally, the syntheses and characterization of the not available standard compounds bisphenol A-p-glycidyl-p′-(3-chloro-2-hydroxypropyl) ether (BADGE.HCl) and bisphenol A-p-(2,3-dihydroxypropyl)-p′-(3-chloro-2-hydroxypropyl) ether (BADGE.HCl.H₂O) are presented. Received: 28 July 1999 / Revised version: 29 October 1999     

Stability of bisphenol A diglycidyl ether and bisphenol F diglycidyl ether in water-based food simulants

Varnishes used for the inner coatings of food cans are often based on epoxy resins or vinylic organosols. The epoxy resins can be produced from bisphenol A (BPA) and bisphenol F (BPF), and these also contain bisphenol A diglycidyl ether (BADGE) or bisphenol F diglycidyl ether (BFDGE) as stabilising components. These compounds may break down during storage and also by the influence of food simulants. The stability of BADGE and BFDGE were studied using reverse-phase gradient high-performance liquid chromatography (RP-HPLC) with ultraviolet detection (UV). Three experimental conditions for spiked simulants were compared: (1) the storage at 25 °C (C1), (2) the storage at 40 °C (C2) and (3) the storage at 25 °C after 15 min heating at 120 °C (C3). Distilled water, 3% acetic acid and 10% ethanol were used as food simulants. It was observed that BADGE is more stabile than BFDGE. The loss of BADGE and BFDGE were minimal in 10% ethanol (39 and 46% at 25 °C, 60 and 69% at 40 °C, respectively) and highest in 3% acetic acid (60 and 63% at 25 °C, 76 and 82% at 40 °C, respectively). At experiment (C3), the hardest conditions, significant degradation was not shown in comparison with conditions (C1) and (C2), contrariwise BADGE and BFDGE in 10% ethanol were minimal degradated at conditions (C3) from all these experiments (loss of 5 and 8%, respectively).     

Occurrence of bisphenol-F-diglycidyl ether (BFDGE) in fish canned in oil

The levels of bisphenol-F-diglycidyl ether (BFDGE) were quantified as part of a European survey on the migration of residues of epoxy resins into oil from canned fish. The contents of BFDGE in cans, lids and fish collected from all 15 Member States of the European Union and Switzerland were analysed in 382 samples. Cans and lids were separately extracted with acetonitrile. The extraction from fish was carried out with hexane followed by re-extraction with acetonitrile. The analysis was performed by reverse phase HPL C with fluorescence detection. BFDGE could be detected in 12% of the fish, 24% of the cans and 18% of the lids. Only 3% of the fish contained BFDGE in concentrations considerably above 1mg/kg. In addition to the presented data, a comparison was made with the levels of BADGE (bisphenol-A-diglycidyl ether)analysed in the same products in the context of a previous study.     

Determination of Bisphenol A diglycidyl ether (BADGE) and its hydrolysis products in canned oily foods from the Austrian market

 Bisphenol A diglycidyl ether (BADGE) is determined in canned oily foods from Austria using a new simplified HPLC method. Samples are extracted with pentane, back extracted with methanol, and finally dissolved in the mobile phase (cyclohexane/tert–butyl methyl ether). Separation is performed on a normal-phase HPLC column using fluorescence detection. Verification of the BADGE-containing peak is carried out by using off-line GC-MS. Additionally, the synthesis and determination of BADGE hydrolysis products, Bisphenol A bis(2,3-dihydroxypropyl) ether (BADGE.2H₂O) and Bisphenol A glycidyl (2,3-dihydroxypropyl) ether (BADGE.H₂O) are presented. From 67 analyzed cans, containing various fatty meat or fish products, 16% were above the maximum quantity of 1 mg/kg tolerated by the European Community, 45% were in the range between 0.1–1 mg/kg, 24% between 0.02 and 0.1 mg/kg, and in 15% the BADGE concentrations were below the detection limit of 0.02 mg/kg. The hydrolysis product BADGE.H₂O was not detected in any sample, whereas BADGE.2H₂O was found in some samples up to a concentration of 0.5 mg/kg. Received: 11 May 1998 / Revised version: 1 July 1998     

Estimation of intake of bisphenol-A-diglycidyl-ether (BADGE) from canned fish consumption in Europe and migration survey

The exposure to bisphenol-A-diglycidyl-ether (BADGE) from canned fish in oil was assessed from consumption data collected for each Member State of the European Union and Switzerland, and migration data from a European survey on 382 samples. Trade figures were used when no consumption data were available. The average consumption of canned fish in Europe was 2.3kg per person per year, with values ranging from 0.2kg per person per year in the United Kingdom to 5.1kg per person per year in Denmark. The exposure to BADGE was calculated as μg per person per day. The data indicated that exposure to BADGE was in the range below 4mg per person per year, i.e. 9 μg per person per day, hence a fairly low exposure in part due to the fact that canned fish is a relatively minor dietary item. An approximation assuming the general figure of a 60kg adult, would thus be 0.15 μg/kg body weight per day. This is a fairly limited exposure considering the provisional limit in food had been set a 1mg/kg and assumed 1kg of food ingested. In countries for which increased exposure was found, the reason was mainly caused by one individual sample exhibiting a high concentration rather than a larger number of samples with mildly elevated concentrations.     

Improved sample extraction and clean-up for the GC-MS determination of BADGE and BFDGE in vegetable oil.

A straightforward method was established for the determination of migration contaminants in olive oil with a special focus on the two can-coating migration compounds bisphenol A diglycidyl ether (BADGE) and bisphenol F diglycidyl ether (BFDGE). The preferred sample preparation was a single liquid-liquid extraction of compounds from the oil into 20% (v/v) methanol in acetonitrile, followed by clean-up with solid-phase extraction on aminopropyl bonded to silica. This purification procedure selectively removed all free fatty acids from the extracts without removing phenolic compounds of interest. The solid-phase extraction columns were used many times by implementing a procedure of washing out the strongly retained fatty acids with 2% acetic acid in methanol. Gas chromatography coupled with full scan (m/z 33-700) electron ionization mass spectrometry was used for the determination of several model compounds in olive oil samples. BADGE and BFDGE could be determined in the 0.05-2 mg kg(-1) range in oil samples with a relative SD of <6% (six replicates). The method was used in an enforcement campaign for the Norwegian Food Control Authority to analyse vegetable oil samples from canned fish-in-oil.     

Monitoring of bisphenol-A-diglycidyl-ether (BADGE) in canned fish in oil

A survey at the European level was initiated on the quantification of bisphenol-A-diglycidyl-ether (BADGE) in canned fish in oil in order to assess the exposure of BADGE. A total of 382 canned fish samples were collected from all 15 Member States and Switzerland and analysed for BADGE in fish. The fish was extracted first with hexane and reextracted with acetonitrile, followed by a membrane filtration and reverse phase HPLC analysis with fluorescence detection. The analysis of the fish showed that about 3% of the samples contained BADGE at a level above 1mg/kg. The samples exceeding the limit by a larger margin were mostly from anchovy cans and cans manufactured in 1991-1995.     

Determination of bisphenol A diglycidyl ether (BADGE) and its derivatives in food: identification and quantification by internal standard

Bisphenol A diglycidyl ether (BADGE) and its reaction products with water and hydrochloric acid have recently been subject to new regulations concerning their migration from food packaging into foodstuff. A method for the simultaneous identification and quantification of these substances and their precursor bisphenol A in food is described introducing bisphenol A di-(3-hydroxypropyl)ether as an internal standard. Analysis was carried out using RP-HPLC gradient elution with fluorescence detection. Additional information in the case of suspect samples was obtained using RP-HPLC with mass selective detection. The described method is validated for the analysis of foodstuffs as well as fatty food simulants. The limits of detection were between 10 and 30 µg/kg of food; recovery experiments gave identical behaviour for all analytes and the internal standard. The enforcement of the specific migration limit set by regulatory standards of the European Union for BADGE and its hydrolysis and hydrochlorination products is possible for producers as well as food quality surveillance institutions.     

国内市场上罐装啤酒中双酚类物质迁出量调查

建立并利用固相萃取-高效液相-荧光法对国内市场上31种罐装啤酒中双酚物的含量进行了调查。方法的检测限为0.02～0.09μg/L,在0.02～50.00μg/L的检测范围内相关系数大于0.99,加标回收率和标准差分别为80.67%～101%和1.01%～4.84%。样品中除双酚E(BPE)没有检出外,双酚A(BPA)、双酚A二缩水甘油醚(BADGE)、双酚F二缩水甘油醚(BFDGE)、双酚B(BPB)和双酚F(BPF)的平均检出浓度分别为2.99、0.41、0.18、0.12、0.12μg/L,检出率分别为100%、83.9%、6.4%、12.9%和6.4%。BPA和BADGE是罐装啤酒中存在的最主要的双酚物,其平均每日摄入量分别估计为0.0160、0.0022μg/kg.bw.d,低于欧盟关于BPA50μg/kg.bw.d的规定。样品中BPA没有超过欧盟规定的0.6mg/L,BADGE的迁移也未高于9mg/L,但是BFDGE的检出是不允许的。目前尚无关于BPF、BPE和BPB的迁移限值。     

食品包装材料中有害物质双酚A二缩水甘油醚 体外代谢研究

目的通过模拟体内代谢,对双酚A二缩水甘油醚(BADGE)的体外基本代谢情况进行研究。方法采用肝微粒体、肝S9 2种体外代谢试剂,通过模拟体内肝脏代谢,对BADGE的代谢行为及其代谢产物进行研究。通过代谢试剂浓度及代谢时间条件的优化,采用高效液相色谱-串联质谱(HPLC-MS/MS)作为检测手段对BADGE的体外代谢产物进行分析确证。结果体外代谢最佳孵化时间为60 min,最佳体外代谢试剂浓度为0.5mg/m L,在肝S9及肝微粒体2种体外代谢试剂的作用下,BADGE发生显著的代谢反应。结论本研究与传统的动物试验相比,节约了时间、精力,对食品包装材料的毒理学研究和安全性评价有重要的推动作用。     

A LC-MS/MS method for the determination of BADGE-related and BFDGE-related compounds in canned fish food samples based on the formation of [M+NH(4)](+) aducts

A new and simple liquid chromatography tandem mass-spectrometry method for the determination of different bisphenol A (BPA) derivatives such as bisphenol A diglycidyl ether (BADGE), bisphenol F diglycidyl ether (BFDGE) and their reaction products with water and hydrochloric acid in different fish food products was developed. The extraction procedure and the chromatographic conditions were optimised for complex food matrices such as fish products. Food samples were homogenised and extracted with a 1:1 solution of acetonitrile-hexane, the solvent was eliminated in a N(2) stream and the extract was reconstituted with 0.5mL of a 0.01M solution of ammonium formate. The sample solution obtained was directly measured by LC-MS/MS without any further purification under the developed conditions. The use of a mobile phase composed by ammonium formate-methanol in a binary gradient mode produced [M+NH(4)](+) aducts for the different BADGEs and BFDGEs. These aduct's fragmentations were employed for the LC-MS/MS quantification of BPA derivatives in canned fish samples. The results of the validation were appropriate: the method was linear for BADGE and its hydrolysed derivatives up to 1000μgkg(-1), for the remaining compounds linearity achieved up to 100μgkg(-1). Quantification limits were in the range 2-10μgkg(-1). RSD (intra and inter-day) was 6-12% and the recovery was comprised between 89% and 109%. Under the optimised conditions, the chromatographic separation was performed in 8min per sample. The method was applied to the determination of BADGE, BFDGE and their reaction products in different samples of canned fish from Spanish origin. Migration results obtained were in compliance with the EU regulations.     

Review of the toxicology, human exposure and safety assessment for bisphenol A diglycidylether (BADGE).

BADGE (whose chemical names are bisphenol A diglycidylether and 2,2-bis(4-(2,3-epoxypropyl)phenyl)propane) is the lowest molecular weight oligomer in commercial epoxy resins and the major component in commercial liquid epoxy resins. The major application areas for epoxy resins are protective coatings and civil engineering. Additional applications include printed circuit boards, composites, adhesives and tooling, while a relatively small amount of epoxy resins (< 10%) finds use in protective coatings inside food and drink cans. The use of BADGE in food-contact applications was first regulated through EC Directive 2002/16/EC and amended in EC Directive 2004/13/EC with migration levels in food-contact applications being generally well below the regulatory thresholds. The paper discusses the commercial use of BADGE focusing on the current knowledge of human exposure from canned food applications. To assess the safety of this application, the exposure data are compared with no adverse effect levels (NOAEL) from various toxicological investigations with BADGE including reproductive and developmental assays, endocrine toxicity investigations, and sub-chronic and chronic assays. Consumer exposure to BADGE is almost exclusively from migration of BADGE from can coatings into food. Using a worst-case scenario that assumes BADGE migrates at the same level into all types of food, the estimated per capita daily intake for a 60-kg individual is approximately 0.16 microg kg(-1) body weight day(-1). A review of one- and two-generation reproduction studies and developmental investigations found no evidence of reproductive or endocrine toxicity, the upper ranges of dosing being determined by maternal toxicity. The lack of endocrine toxicity in the reproductive and developmental toxicological tests is supported by negative results from both in vivo and in vitro assays designed specifically to detect oestrogenic and androgenic properties of BADGE. An examination of data from sub-chronic and chronic toxicological studies support a NOAEL of 50 mg kg(-1) body weight day(-1) from the 90-day study, and a NOAEL of 15 mg kg(-1) body weight day(-1) (male rats) from the 2-year carcinogenicity study. Both NOAELS are considered appropriate for risk assessment. Comparing the estimated daily human intake of 0.16 microg kg(-1) body weight day(-1) with the NOAELS of 50 and 15 mg kg(-1) body weight day(-1) shows human exposure to BADGE from can coatings is between 250,000 and 100,000-fold lower than the NOAELs from the most sensitive toxicology tests. These large margins of safety together with lack of reproductive, developmental, endocrine and carcinogenic effects supports the continued use of BADGE for use in articles intended to come into contact with foodstuffs.     

食品金属罐中14种双酚类物质迁移量的同时测定及杀菌过程对其迁移的影响

为了调查国内食品金属罐中双酚类物质的迁移水平,本文建立了同时测定食品金属罐中14种双酚类物质迁移量的高效液相色谱法,并研究了杀菌过程对双酚类物质迁移的影响及食品金属罐中双酚类物质的迁移规律。结果表明,14种双酚类物质在4种食品模拟物（4%体积乙酸、10%体积乙醇、50%体积乙醇和异辛烷）中线性关系良好,加标回收率为83.67%～107.05%,精密度范围为2.32%～7.67%,该方法的精密度和准确度较好,可用于食品金属罐中14种双酚类物质迁移量的检测分析。对市场上9种罐头和饮料用金属罐中的14种双酚类物质的迁移量进行了同时测定,发现有7种双酚类物质检出,无双酚A及其类似物的检出。基于欧盟限量标准要求,发现午餐肉罐头中的双酚A-（2-3-二羟基丙基）缩水甘油醚（BADGE·H₂O）、牡蛎葛根饮料中的双酚A-二（2-3-二羟基丙基）醚（BADGE·2H₂O）和黑莓罐中的双酚F-（2-3-二羟基丙基醚）（BFDGE·2H₂O）存在一定的迁移风险。此外,杀菌过程影响食品金属罐中双酚类物质的迁移种类和迁移量。迁移试验结束后,经过杀菌的金属罐中仅检测出BADGE·2H₂O,而未经杀菌的金属罐中同时检测到BADGE·2H₂O和双酚A-（3-氯-2羟丙基）（2-3-二羟基丙基）缩水甘油醚（BADGE·H₂O·HCl）。另外,食品模拟物的类型影响着双酚类物质的迁移量和迁移种类,且随着迁移温度的升高和迁移时间的增加,双酚类物质的迁移量逐渐升高直至平衡。     

Survey of bisphenol A and bisphenol F in canned foods.

Bisphenol A (BPA) and bisphenol F (BPF) have been determined in a range of canned foods. Sixty-two different canned foods were purchased from retail outlets in the UK from January to November 2000 and the contents extracted and analysed by GC-MS for BPA and BPF isomers. The following canned products were analysed: fish in aqueous media, 10 samples; vegetables, 10; beverages, 11; soup, 10; desserts, five; fruit, two; infant formula, four; pasta, five; and meat products, five. BPF isomers were not detected in any of the canned foods with detection limits of 0.005 mg kg(-1) for the 2,2' and 2,4' isomers and 0.01 mg kg(-1) for the 4,4' isomer. BPA was detected in 38 samples with a detection limit of 0.002 mg kg(-1). Of these, BPA was quantified in 37 canned foods at levels from 0.007 mg kg(-1), with one sample of meat containing a mean level of 0.38 mg kg(-1). All other samples contained <0.07 mg kg(-1) BPA.     

Estimates of per capita exposure to substances migrating from canned foods and beverages.

A study was undertaken by European industry to estimate the consumption of canned beverages and foodstuffs. European can production data were used with adjustments for imports into and out of the EU. It was further assumed that can production, with adjustments, equalled consumption. Owing to the lack of actual consumption country-by-country or household-by-household data throughout Europe, only per capita estimates of consumption were possible. Data were compiled country-by-country for seven major can-producing EU Member States and for eight different types of canned food and two types of canned beverage (beer and soft drinks). The per capita consumption of canned foods was 1.1 cans/person/week, and consumption of canned fish was estimated as 2.2 kg/person/year. The estimate of per capita consumption of canned food was 62 g/person/day or 22.6 kg/person/year. Canned beverages account for about 60% of the consumption of canned foodstuffs. The usefulness of per capita consumption of beverages is questionable because consumption habits may vary more widely than those for canned foods. However, as the migration into beverages is insignificant, these data were added for completeness. Per capita consumption of canned beverages is 67 cans/person/year or 61 g/person/day. From the average can sizes, the surface area of the cans consumed was estimated. The per capita surface area exposure was 0.55 dm(2)/person/day for canned foods and 0.55 dm(2)/person/day for canned beverages, giving 1.1 dm(2)/person/day. Migration of a substance at 0.02 mg dm(2) gives an exposure of 0.01 mg/person/day assuming a per capita consumption, using a surface area model. Migration at 0.12 mg kg(-1) in food gives an exposure of 0.007 mg/person/day using a weight model. Both models assumed migration into all food types at the same level, which is highly unrealistic. Exposure to BADGE from canned foods has been used as a case study. The best estimate for a worst case per capita exposure to BADGE and relevant derivatives was between 6 and 10 micro g/person/day, depending upon the approach and assumptions used.     

High consumption increases sensitivity to after-flavor of canned coffee beverages

BackgroundConsumers’ dietary habits affect perception of flavor attributes of common foods. One such flavor attribute is after-taste, but the definition of this term in the context of flavor perception is not consistent among studies. To address this issue, we refer collectively to the complex sensation perceived after swallowing or spitting out foods as “after-flavor”, and considered each flavor attribute (for example, bitterness and retronasal aroma) as a component of after-flavor. In this study, we examined how consumption of canned coffee beverages in daily life affects sensitivity to the after-flavor of these beverages. We performed time–intensity evaluation of bitterness and retronasal aroma after participants swallowed three different canned coffee beverages. We classified participants into two groups based on their consumption of canned coffee beverages in daily life: the relatively high-consumption group, who consumed at least one canned coffee beverages per week, and the relatively low-consumption group, who consumed less than one canned coffee beverages per week. We compared the time courses of perceived intensity of bitterness and retronasal aroma between these two groups.ResultsTime courses of perceived intensity of bitterness in two of the canned coffee beverages, and retronasal aroma in all three canned coffee beverages were significantly higher in the relatively high-consumption group.ConclusionsFamiliarization with canned coffee beverages due to increased consumption in daily life might significantly promote sensitivity to the after-flavor of such beverages.     

Bisphenol A diglycidyl ether (BADGE) migrating from packaging material 'disappears' in food: reaction with food components

Bisphenol A diglycidyl ether (BADGE) is widely used as a monomer for coatings and adhesives for food-contact applications. Previous publications indicate that, after migration from packaging into foodstuffs, BADGE undergoes various reactions with unidentified food components. In order to elucidate the fate of BADGE, losses were determined after incubation with different foodstuffs and food components. Food proteins were identified as the main reaction partner with BADGE. Adduct formation was found with nucleophilic side-chains of amino acids. In vitro, cysteine exhibited significant activity. The previously reported occurrence of methylthio-derivatives of BADGE in foodstuffs was shown to originate from the reaction of BADGE with methionine. BADGE-methylthio derivatives can, therefore, be used as marker substances in foodstuffs for protein reactions with BADGE. The reported results offer a new viewpoint on the evaluation of BADGE migration. The hydrolysis and hydrochlorination derivatives subject to European legislation make up only a fraction of the totally migrated BADGE, and a further concern is that the toxic or allergenic potential of the protein adducts are unknown.     

Bisphenol A diglycidyl ether (BADGE) migrating from packaging material 'disappears' in food: reaction with food components.

Bisphenol A diglycidyl ether (BADGE) is widely used as a monomer for coatings and adhesives for food-contact applications. Previous publications indicate that, after migration from packaging into foodstuffs, BADGE undergoes various reactions with unidentified food components. In order to elucidate the fate of BADGE, losses were determined after incubation with different foodstuffs and food components. Food proteins were identified as the main reaction partner with BADGE. Adduct formation was found with nucleophilic side-chains of amino acids. In vitro, cysteine exhibited significant activity. The previously reported occurrence of methylthio-derivatives of BADGE in foodstuffs was shown to originate from the reaction of BADGE with methionine. BADGE-methylthio derivatives can, therefore, be used as marker substances in foodstuffs for protein reactions with BADGE. The reported results offer a new viewpoint on the evaluation of BADGE migration. The hydrolysis and hydrochlorination derivatives subject to European legislation make up only a fraction of the totally migrated BADGE, and a further concern is that the toxic or allergenic potential of the protein adducts are unknown.