Risk assessment of bisphenol related compounds in canned convenience foods, olives, olive oil, and canned soft drinks in Turkey.

The presence of Bisphenol A (BPA), Bisphenol A Diglycidyl Ether (BADGE), and their derivatives in seventy-nine samples of food products available in Turkish stores was determined using ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Among Bisphenol A and its analogues, BPA was the most detected migrant with 56.97%. Fish products had the highest level of BPA with 0.102 mg/kg although only three fish samples exceeded the Specific Migration Limit (SML) for BPA of 0.05 mg/kg of food. The BPF, BPS, and BPB in all analyzed foods ranged between 0-0.021, 0-0.036, and 0.072 mg/kg, respectively. BADGE derivates, BADGE·2H2O and cyclo-di-BADGE (CdB) were present in 57 and 52 samples with concentrations ranging between 0-0.354, and 0-1.056 mg/kg, respectively. All the analyzed traditional Turkish ready-to-eat meals and fish products were contaminated with BADGE·2H2O and CdB. The overall levels of BADGE and the derivates were below the specific migration limit. CdB was found at higher concentrations in traditional Turkish ready-to-eat meals, up to 1.056 mg/kg. The CdB concentration in most of the samples was above the highest figure with 0.05 mg/kg authorized by the German Federal Institute for Risk Assessment. The predominant chlorinated derivative was BADGE·H2O·HCl which was found in thirty-seven samples in the range of 0.007-0.061 mg/kg.

Subacute exposure to bisphenol F diglycidyl-ether induces chronic dermatitis characterized by psoriasis-like skin inflammation in mice.

Bisphenol F diglycidyl ether (BFDGE) is widely used in the synthesis process of plastic products. While exposure to bisphenol A diglycidyl ether (BADGE), which has a similar structure to BFDGE and which is used for the same purpose, has been reported to cause health risks, there is still little information on BFDGE. Because it is estimated that the industrial workers are exposed to large amounts of BFDGE, the health risks associated with BFDGE exposure need to be clarified. We investigated the toxicity of cutaneous exposure to BFDGE using an in vitro evaluation system and a mouse exposure model. The tumorigenic potential of BFDGE was confirmed by the Bhas 42 cell transformation assay, which showed that BFDGE has both promoter and initiator activity, in vitro. A single dermal application of BFDGE was associated with minor contact hypersensitivity symptoms. In contrast, repeated dermal exposure to BFDGE for 2 weeks induced persistent acute inflammation with features similar to inflammation in human psoriasis. This is the first report evaluating the toxicity of BFDGE in animals, and we showed that BFDGE carries a health risk of inducing skin dermatitis similar to that in human psoriasis in an exposure period-dependent manner.

Monitoring of bisphenol A diglycidyl ether (BADGE) and some derivatives in fish products in the Turkey market.

The exposure to bisphenols and their derivatives was assessed in 33 fish products sold in Turkey using high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS). BADGE was determined in only four samples at concentrations ranging between 0.06 and 0.22 mg/kg. As the most abundant bisphenol groups, BADGE-hydrolyzed products such as BADGE·H2O and BADGE·2H2O were present in nine and fourteen samples in the range between 0.06-0.16 and 0.06-0.72 mg/kg, respectively. The total concentration of BADGE and hydrolyzed products was below the specific migration limit (SML) value of 9 mg/kg food, which in the European Union stated as tolerable. Chlorinated derivatives of BADGE were detected in fewer samples compared with hydrolyzed ones. BADGE·H2O·HCl was the predominant migrant among chlorinated derivatives and was present in seven samples in a range between 0.02 and 0.06 mg/kg. All other samples contained less than or equal to 0.03 mg/kg of BADGE·HCl and BADGE·2HCl. The sum of these derivatives was lower than the SML value (1 mg/kg) of BADGE chlorohydrins legislated by the European Union. Besides these migrants, the analyzed samples did not contain any BFDGE and 3R-NOGE, which are prohibited in manufacturing food contact materials.

LC-MS/MS analysis of BADGE, NOGEs, and their derivatives migrated from food and beverage metal cans.

A simple and novel method based on liquid chromatography-tandem mass spectrometry (LC-MS/MS) was developed and validated to determine the levels of 10 compounds (bisphenol A diglycidyl ether (BADGE), novolac-glycidyl ethers (NOGEs), and their related compounds) migrated from food and beverage cans into food simulants. Method validation showed acceptable linearity, precision, and accuracy. The detection limits ranged from 0.28 to 14.8 µg L-1, and the quantification limits ranged from 0.94 to 49.3 µg L-1. Water, 4% acetic acid, 50% ethanol, and n-heptane were employed as food simulants for the migration tests, and the developed LC-MS/MS method was applied to 104 epoxy-coated beverage and food metal cans. Only BADGE∙2H2O and BADGE were detected; the levels were below the specific migration limit. Based on the obtained migration results, the estimated daily intakes (EDIs) of BADGE∙2H2O and BADGE were calculated. Exposure assessments were conducted to compare the EDI with the tolerable daily intake (TDI), with a relatively low percentage of the TDI being reported. NOGE and its related compounds were not detected in the monitored cans. Long-term storage tests were also conducted at 60°C over 30 days. Only BADGE∙2H2O was detected in all food simulants, except for n-heptane, and the maximum amount detected was 114.6 µg L-1 in 50% ethanol.

Human phase I in vitro liver metabolism of two bisphenolic diglycidyl ethers BADGE and BFDGE.

Root canal sealers are commonly used to endodontically treat teeth with periapical infections. Some root canal sealers based on epoxy resin contain bisphenol A diglycidyl ether (BADGE) and bisphenol F diglycidyl ether (BFDGE). The presence of these chemicals is of concern due to the close contact to the blood stream at the apex and the long setting times of up to 24 h. These chemicals, or any of their degradation products or metabolites, can then exert their toxic effects before being excreted. This study aimed to identify the phase I in vitro biotransformation products of BADGE and BFDGE using human liver microsomes. During incubation with microsomal fractions, the epoxides were rapidly hydrolysed in a NADPH independent manner resulting in the formation of BADGE.2H2O and BFDGE.2H2O. Further, oxidative reactions, such as hydroxylation and carboxylation, generated other BADGE metabolites, such as BADGE.2H2O-OH and BADGE.H2O.COOH, respectively. For BFDGE, further oxidation of BFDGE.2H2O led to the newly reported carboxylic acid, BFDGE.H2O.COOH. In total, three specific metabolites have been identified which can serve in future human biomonitoring studies of BADGE and BFDGE.

Stabilities of bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, and their derivatives under controlled conditions analyzed using liquid chromatography coupled with tandem mass spectrometry.

Bisphenol A diglycidyl ether (BADGE), bisphenol F diglycydyl ether (BFDGE), and their related compounds are widely used as precursors in production of epoxy resins. The high reactivity of these compounds makes the development of analytical methodologies that ensure appropriate metrological accuracy crucial. Consequently, we aimed to determine whether and to what extent the composition of the solution and storage conditions affect the stability of selected BADGE and BFDGE derivatives. The stabilities of these compounds were studied using liquid chromatography-tandem mass spectrometry with electrospray ionization (HPLC-ESI-MS/MS). The chromatographic method elaborated here has allowed for separation of the analytes in time shorter than 6 min, for both methanol and acetonitrile-based mobile phases. The obtained calibration curves for all analytes were linear in the range tested. The values of limit of detection (LODs) were in the range of 0.91-2.7 ng/mL, while values of limit of quantitation (LOQs) were in the range of 2.7-5.7 ng/mL. The chosen experimental conditions were compared in terms of the content of organic solvent in solution, storage temperature, and time. Our results show that the content of BADGE, BADGE·HCl, BFDGE, three-ring NOGE decreased with increasing water content (> 40% v/v). For BADGE and three-ring NOGE, significant changes in concentration were noted as early as 24 h after the test solutions had been prepared. In addition, a reduction in the storage temperature (4 to - 20 °C) reduced the rate of transformation of the monitored analytes. Our study will increase quality control in future research and may increase the reliability of the obtained results. Graphical abstract.