Migration Of Bisphenol Research Articles

Determination of bisphenol A in barreled drinking water by a SPE–LC–MS method

A quantitative method was established to determine the well-known endocrine disruptor bisphenol A (BPA) in barreled drinking water. Samples were pretreated by solid phase extraction (SPE), and then analyzed by liquid chromatography–mass spectrometry (LC–MS). Working standard solutions were obtained by pretreatment of a series of aqueous standard solutions over the concentration range of 122.9–1190.7 ng L−1. The linear calibration curve was Y = 69.4X + 2206.2 with the correlation coefficient (R2) of 0.9929. The average recoveries from spiked samples were more than 91.6%. The relative standard deviations (n = 6) were less than 9.6%. The method allowed the detection of 7.0 ng L−1 BPA in barreled drinking water. Typical barreled drinking water products in the market were detected. As results, thirty-five of fifty-two commercial samples were found to contain BPA with a maximum concentration of 898.7 ng L−1. The occurrence of BPA in barreled drinking water may be due to the pollution of raw water, the inefficiency of purification processes and the migration of BPA from barrels. The daily exposure of adults to BPA through drinking barreled drinking water is far below the current human tolerable daily intake (TDI) set by European Food Safety Authority (EFSA).

Molecular dynamics study of the migration of Bisphenol A from polycarbonate into food simulants

The leaching of bisphenol A (BPA) from polycarbonate (PC) has raised environmental and health concerns. Here, we designed molecular dynamics simulations to investigate molecular mechanisms underlying the migration of BPA from PC into different food simulants. The simulation results illustrated that BPA molecules are much easier to migrate into ethanol solution than water and palmitic acid. The investigation of nanostructure, solubility and diffusivity demonstrated that the leaching of BPA happens only when the solvent possesses small molecular size and good solubility to PC and BPA. These results expand our knowledge of migration of small molecules in polymer matrices.

Study on the migration of bisphenols from plastic food contact materials to food simulants

A rapid method for the detection of bisphenols was established by ultra performance convergence chromatography (UPC2). The migration rules of bisphenols in four different simulants including of pure water, acetic acid, ethanol and isooctane were first studied, and the effect of extraction solvent on recovery of bisphenols in aqueous simulants was also investigated. Furthermore, the influence of extraction solvent on recovery of bisphenols in aqueous simulants was discussed, and the relationship between migration amount of bisphenols and food simulants, migration time, migration temperature and other factors were explored. The experimental results showed that toluene exhibited the optimal extraction efficiency for bisphenols in aqueous simulants; bisphenols presented the most obvious migration in fatty food simulants; the migration amount of bisphenols increased with the extension of time; the migration rate and amount of bisphenols also enhanced with the increment of contact temperature.

Migration of bisphenol a into food simulants and meat rations during initial time of storage

AbstractThe aim of this work was to assume the amount of BPA that can migrate to food packed into the cans coated by epoxy‐phenolic lacquer. The assumption was made by determining the amount of BPA which migrates from the inner can coating to different food simulants: 3% acetic acid, 10% ethanol, their mixture (3% acetic acid +10% ethanol), and 50% ethanol. The examined tinplate cans were made by the special requirements of the Serbian Armed Forces. Further, the effect of the sterilization process and the very initial time of storage (15–105 days), on the level of BPA in the canned meatballs in tomato sauce, which are in the regular use of the Serbian Armed Forces, was examined. The BPA content was determined by the high performance liquid chromatography‐mass spectrometry (HPLC–MS), and compared with BPA content found in the food simulants.

Migration of pseudoestrogen bisphenol A from various types of paper with thermochromic prints to artificial sweat solutions

Thermochromic inks, materials that change color at a certain temperature, are increasingly used on papers and other materials in the areas of design, commercials, and security printing. Pseudo-estrogen bisphenol A (BPA) may be one of their main compounds present in mass fractions of up to several percent. In this work, the mass fractions of BPA in thermochromic prints on seven types of paper were determined. Migration of BPA from the surface of the thermochromic print to artificial sweat solutions was investigated as well. Total amount of BPA in papers with thermochromic prints was determined by an HPLC-UV method with ultrasonic-assisted extraction in methanol developed and validated in this work. Total amount of BPA, which ranged from 0.126 to 0.778 mg/g, was compared with the amounts extracted under the same conditions in two artificial human sweat solutions, which differed in chemical composition, ionic strength, and pH-value. Mass fractions of BPA extracted with artificial sweat solutions were from 0.047 to 0.175 mg/g with respect to the mass of the paper. On average, the mass fraction of BPA was four times less when extracted with artificial sweat solutions than the maximal amount extracted with methanol. The amounts of extracted BPA raise a concern of health risk through dermal exposure to BPA from thermochromic prints on paper.

Review on metal packaging: materials, forms, food applications, safety and recyclability.

Metal based packaging materials provide excellent barrier properties and hence, being used widely in food packaging applications. They are used in different package forms and also as closures such as for glass bottles and composite cans. Major health and product safety concerns of metal packaging comprise migration of bisphenol A, lead, cadmium, mercury, aluminium, iron, nickel, bulging of cans, tin dissolution, blackening and corrosion. Metals are not inert to food products, hence coated with protective lacquers to prevent metal-food interaction and migration of metal components. Metal packaging materials have lower global warming potential and higher recyclability due to their magnetic properties which helps in easier segregation. An attempt has been made in this article to review the metal packaging materials used in food industry and Indian Standard specifications, their safety and recyclability aspects.

Dispersive solid-phase extraction of bisphenols migrated from plastic food packaging materials with cetyltrimethylammonium bromide-intercalated zinc oxide

The migration of bisphenols (BPs) can take place from plastic packaging materials into freshly cooked takeaway food, especially at high temperatures. In this study, cetyltrimethylammonium bromide-intercalated zinc oxide (ZnO@CTAB) was developed and used to extract the migration of BPs (bisphenol A and bisphenol AF) from disposable plastic materials to contained food simulates. Several experimental parameters that influence extraction efficiency were investigated. Under optimal conditions, a sensitive dispersive solid-phase extraction method based on ZnO@CTAB was proposed for the analysis of BPs coupled with ultra-high performance liquid chromatography and time-of-flight mass spectrometry. The method exhibited good linearity of calibration, high recovery (97.63–109.33%), low limits of detection 0.027–0.030 μg L−1, and acceptable precisions. The developed method was used to carry out a migration test from two disposable plastic bags and a disposable plastic container, using distilled water at 100 °C as a hot liquid food simulant. The migration concentrations of bisphenol AF was found to be 0.42 μg L−1 and 0.86 μg L−1 for the two types of disposable plastic bags, and the concentration of bisphenol A was 0.49 μg L−1 for disposable plastic container. The proposed method was also applied to investigate the migration of BPAF from the disposable plastic bags to different food simulants, revealing that the release of BPAF levels depended on the polarity of the liquid food components.

PH dependence of the binding interactions between humic acids and bisphenol A - A thermodynamic perspective

The wide application of bisphenol A (BPA) leads to the emergence of BPA residuals in natural water environments. Dissolved organic matter (DOM) existed in water can bind with BPA, hence influencing the migration and transformation of BPA in aquatic environments. pH is a crucial factor governing the binding interactions between DOM and BPA. However, the mechanisms driven the binding process under different pH conditions are still unclear. In this study, the interactions between BPA and humic acids (HA), a primary component of DOM, are investigated over a wide pH range of 3–12 by integrating fluorescence quenching, dynamic light scattering and microcalorimetry. pH dependence of the binding interactions between HA and BPA are interpreted from a thermodynamic perspective. The results indicate that HA can spontaneously interact with BPA to form a stable HA-BPA complex. With the increasing pH, the binding interactions change from entropy driven to entropy-enthalpy co-driven. Hydrophobic force dominate the binding interactions under acidic condition. The synergy of hydrophobic force and hydrogen bond promotes the binding process under neutral condition. Under alkaline conditions, electrostatic repulsion participates the binding process in addition to hydrophobic force and hydrogen bond, weakening the binding strength. Therefore, neutral pH is favorable for HA to bind with BPA, consequently enhancing the dissolution of BPA in natural water bodies. The results are beneficial to better understand the pH dependent distribution of BPA in aquatic environments.

LC-MS/MS analysis of bisphenol S and five other bisphenols in total diet food samples

ABSTRACTIt is already known that bisphenol S (BPS) has been used as a substitute for BPA in thermal papers in recent years. It is not clear, however, if BPS has also been used to replace BPA in can coatings as currently being speculated due to a lack of credible studies on migration of BPS from can coatings and occurrence data of BPS in foods. In this study, an LC-MS/MS method was developed for the analysis of BPS, along with several other bisphenols, and method detection limits for BPS varied from 0.0017 to 3.1 ng/g depending on the type of sample matrix and the amount of sample analysed. This method was used to analyse 159 different food composite samples from a recent Canadian total diet study. Bisphenol E (BPE), bisphenol B (BPB), and bisphenol AF (BPAF) were not detected in any of the 159 food composite samples, bisphenol F (BPF) was detected in only three samples (25–2360 ng/g), and bisphenol A (BPA) was detected in 10 samples (5.3–41 ng/g) which were all prepared from canned foods. BPS was not detected in any of the canned food composite samples but was detected in nine food composite samples prepared from meat and meat products (1.2–35 ng/g), indicating sources for BPS other than can coatings may be possible, which will be investigated in future studies.

Insights into thermodynamic mechanisms driving bisphenol A (BPA) binding to extracellular polymeric substances (EPS) of activated sludge

Bisphenol A (BPA) in wastewater has high risks of causing biological feminization. During the wastewater treatment process, large amounts of BPA are accumulated in activated sludge. However, the mechanisms of BPA interacted with activated sludge are still unclear. Especially, the roles of extracellular polymeric substances (EPS), which are major components of activated sludge, in the removal of BPA have never been concerned. In this study, the binding interactions between sludge EPS and BPA are explored combining fluorescence spectroscopy and dynamic light scattering. The thermodynamic mechanisms driving the binding behavior of BPA to EPS are illustrated by isothermal titration calorimetry. The results indicate that the binding interaction between BPA and EPS is spontaneous. BPA mainly binds with the proteins of EPS by hydrophobic association. The random-coiled structure of EPS transforms into relatively condensed cores after binding with BPA. A neutral pH, high ionic strength, and high temperature promote the binding process, facilitating to stabilize BPA in sludge EPS. This study provides new insights into the roles of sludge EPS in the migration and removal of BPA in activated sludge system.

A new solvent extraction method with gas chromatography–Mass spectrometry for bisphenol a determination in canned foods

A new reliable simple solvent extraction method for the endocrine disruptor bisphenol A (BPA) in canned food was developed employing an aqueous basic extraction solution of 0.25 M K2CO3/0.10 M NaOH after spiking with BPA-d16 as internal standard. The BPA was next extracted into diethyl ether after solution acidification to pH = 4 and filtration. Homogenous acetylation at dry basic conditions (acetic anhydride as derivatization agent and solvent with sodium acetate as catalyst) after diethyl ether evaporation was carried out for 30 min at 110 °C. Detection of the acetylated BPA was carried out by gas chromatography–electrospray ionization/mass spectrometry (GC–EI/MS) in the selected ion monitoring (SIM) mode with pulsed split-less mode. The method was applicable in terms of eliminating the use of solvents like acetonitrile for the extraction step, where relatively long evaporation times may have been needed to evaporate acetonitrile. Also, removing lipids and precipitating most of the proteins at acidic conditions (pH = 4) prior to diethyl ether extraction can replace the often used heptane or hexane or solid sorbents. The method was tested linear with limit of linearity (LOL = 750 μg/L) and with coefficient of determination (R2= 0.998), repeatable with relative standard deviation (RSDr < 7%) with instrument detection limit (IDL) of 0.01 μg/L and limit of quantitation (LOQ) of 0.034 μg/L. The method detection limit (MDL) ranged from 0.3 μg/kg to 3.2 μg/kg based on 1 g sample (wet weight). Recovery ranged from 85% to 94% with the relative standard deviations of 2%–13%. BPA concentrations in tested canned foods from outlet stores ranged from <MDL to 57.4 ± (2.6) μg/kg which were below the specific limit for BPA migration in food proposed by the European Union (EU) and within the food safety and quality criteria. The extraction and derivatization steps for BPA were unique and have not been reported in literature.

Migration of Bisphenol A from Can Coatings into Beverages at the End of Shelf Life Compared to Regulated Test Conditions

Beverage cans are used for energy drinks, soft-drinks, sparkling waters, and beer. Bisphenol A is still part of the formulation of epoxy coatings of beverage cans. Due to concerns that bisphenol A acts as an endocrine-active substance, the migration of bisphenol A is restricted. Typically, the migration from beverage cans is tested at elevated temperatures into food simulants, like 20% ethanol in water. However, comparison tests of the migration of bisphenol A at the end of shelf life, with the migration into ethanolic food simulants, are not available in the scientific literature. The aim of the study was to determine the migration of the migration of bisphenol A into real beverages, compared to routine migration tests into the European official food simulant of 20% ethanol at 40 °C and 60 °C after storage for 10 days. As a result, bisphenol A-containing coatings show a considerably higher migration when tested at 60 °C in comparison to 40 °C. On the other hand, migration into energy drinks and coke, from the same coatings at the end of shelf life when stored at room temperature, was below the detection limit in either case. As expected, migration values of bisphenol A below the analytical detection limits were observed for any test conditions from the coating labeled bisphenol A-free. Spiking tests show that bisphenol A is stable in real beverages. Therefore, it can be concluded that the accelerated migration tests with 20% ethanol at the test conditions 10 d at 40 °C and 10 d at 60 °C significantly overestimate the real migration into beverages at the end of shelf life. This overestimation of the migration of bisphenol A is due to swelling of the epoxy can coating by the ethanolic food simulant. These findings were supported by migration modeling based on diffusion coefficients predicted for polyethylene terephthalate.

Influence of a storage conditions on migration of bisphenol A from epoxy-phenolic coating to canned meat products

The migration of bisphenol A (BPA) from epoxy-phenolic can coating into canned meat products, produced for the needs of the Serbian Armed Forces, was investigated in this work. The tinplate cans were made according to the special military demands, filled with the beef goulash or the meatballs in tomato sauce, and preserved by sterilization. The structure of internal can coating was analyzed by FTIR spectroscopy. The migration of BPA into content of the cans was investigated after storage under regular conditions in typical military facilities. The samples of beef goulash (BG) produced in 2010-2016, and the meatballs in tomato sauce (MB) produced in 2014?2017 were tested for the presence of BPA. Thereafter, the impact of storage temperature and degree of can damage on BPA migration was examined. Both meat products were thermostated on 20 and 40 ?C, and BPA level was measured after 3, 6, 9 and 12 months of storage. The level of BPA was determined in the content of undamaged cans, and cans with lower and higher degree of damage. The BPA was extracted from food with acetonitrile and the extracts were purified by QuEChERS procedure. The level of BPA was determined by LC?MS.

BPA, BADGE and analogues: A new multi-analyte LC-ESI-MS/MS method for their determination and their in vitro (anti)estrogenic and (anti)androgenic properties

Information on the occurrence and endocrine potencies of analogues of bisphenol A (BPA) and diglycidyl ester derivatives (BDGEs) of BPA and BPF is limited. Such information is, however, important as the current debate on BPA and the lowered BPA migration limit in Europe may provide an incentive for application of structural analogues. A new sensitive multi-analyte LC-ESI-MS/MS method was developed to measure 17 bisphenols (BPs) and 6 BDGEs in food, beverages and drinkware. Yeast based bioassays were used to determine the in vitro (anti)estrogenic and (anti)androgenic properties of these and 7 additional BPs and BDGEs. Drinkware of polycarbonate and other materials were analysed for BPs and BDGEs. Only BPA and BPS and both at trace levels were found in a few containers. A limited number of (canned) foods and beverages were also analysed. BPA was the most frequently detected BP (ranged from 0.03 ng mL−1 in a beverage sample to 68 ng g−1 in food). Other BPs detected were BPS, 2,2-BPF and 4,4-BPF. In addition BADGE, BADGE.HCl, BADGE.H2O and BADGE.2H2O were detected from 0.08 ng mL−1 in a beverage sample to 3.3 ng g−1 in food. In vitro testing showed that most BPs exhibited an equal or higher estrogenic potency than BPA and most of them also showed a higher anti-androgenic potency, i.e. BPB, BPCl, BPC, BPE, 4,4-BPF, BPP, BPAF, and BPTMC. Some BPs and BDGEs were not estrogenic, but showed an anti-estrogenic effect and were anti-androgenic too. BPS was only weakly estrogenic and BADGE.2H2O and BFDGE.2H2O showed no in vitro activity. The present data show that in addition to BPA, other BPs and BDGEs can be present in food and drinks, some displaying in vitro endocrine activities.

ANALYSIS OF BISPHENOL A IN INDONESIAN CANNED FOOD BY GAS CHROMATOGRAPHY

Objective: This study aimed to design and optimize a gas chromatography-flame ionization detection (GC-FID) method to determine the bisphenol A (BPA)content in Indonesian canned food samples.Methods: GC with Hewlett-Packard-1 capillary columns (length, 30 m; inside diameter, 0.25 mm; and film thickness, 0.25 μm) was used with a columntemperature of 150°C that was programmed to increase by 10°C/min to 260°C. Injector and detector temperatures were 280 and 300°C, respectively,the gas flow rate was 1.0 mL/min, and injection volume was 3.0 μL. Three types of canned food samples were prepared by ethyl acetate extraction andstored under four different conditions (4–8°C, 25–30°C, 40°C for 30 min, and 40°C for 60 min) to determine BPA migration levels.Results: Method validation (system compatibility, selectivity, calibration curve linearity, accuracy, and precision) was acceptable for BPAconcentrations ranging from 2 to 15 μg/mL, with a coefficient of correlation of 0.99983. The limits of detection and quantitation were 0.287 and0.956 μg/mL, respectively. Only one canned food sample type (Group A) showed BPA contamination under all storage conditions and exceeded therecommended guidelines for daily ingestion.Conclusion: The optimized GC-FID method was selective and relatively sensitive in the detection and quantitation of BPA. Furthermore, higherstorage temperatures and durations increased the level of BPA migration into food.

A Review of Plastics Use in Winemaking: HACCP Considerations

Use of plastics is ubiquitous in the food and beverage industries, with expanding usage in wine production. Common plastic additives, used to modify and improve applicability and durability of plastics, include phthalate plasticizers and bisphenols. Phthalates are used in many products, including polyvinyl chloride (PVC), lubricants, and emulsifying agents. Bisphenols such as bisphenol A (BPA) and related BPA non-intent (BPA-NI) alternatives are used to harden plastics and are commonly used in polycarbonate plastics and epoxy coatings. Migration of bisphenols and plasticizers into wine from plastic containers and closures has been studied using analytical tools such as gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry. Foodstuffs can become contaminated with plastic additives through food-contact processing and packaging materials, leading to environmental and human health concerns. This work reviews current food product use and regulations regarding plastic additives and potential leachates, particularly in wines, hazard analysis and critical control points approaches, alternative plasticizers, and bio-based plastics.

A novel air-assisted liquid-liquid microextraction based on in-situ phase separation for the HPLC determination of bisphenols migration from disposable lunch boxes to contacting water

In this study, a novel air-assisted liquid-liquid microextraction (AALLME) method was developed for the HPLC determination of bisphenols migration from disposable plastic lunch box to contacting water. The AALLME was carried out in commercially-available medical plastic syringes with low-density extraction solvent (n-octanol), and the reaction of NaHCO3 and HCl was introduced to simultaneously induce the in-situ phase separation and salt effect. After the AALLME processes, the upper organic phase was pushed into the end of syringes (narrow tube) by moving the piston so that it could be readily collected for the HPLC analysis. The factors including the type and volume of extraction solvent, NaHCO3 addition and extraction cycles were optimized. Under the optimal conditions, the limits of detection (LODs) for target bisphenols were evaluated to be 0.2–0.7 μg L−1, and good linearities with correlation coefficients higher than 0.9955 were obtained. The recoveries for target bisphenols ranged from 80% to 106%, with the relative standard deviations (RSDs) of 4.4–14.1%. The proposed method was successfully applied to investigate the migration of bisphenols from the disposable plastic lunch boxes to the contacting water, revealing that compared to the conventional water-bath heating, the microwave heating could induce the significant migration of bisphenols in a much shorter time.

Quality Control of the Migration of Bisphenol a from Plastic Packaging into Iranian Brands of Food Grade Oils

Background: Bis-phenol A (BPA) can migrate into food stuff from packaging materials and accounts for food contamination. This research was designed to measure BPA contamination in the Iranian brands of food grade oils and to find out the possible effect of production date on the amount of BPA migration. Methods: Ten well-known and top selling oils packed in various containers, were selected and sampled according to their batch number and production date stated on the label. Subsequently, BPA was extracted by reverse phase dispersive liquid-liquid extraction (RP-DLLME) method and quantified by HPLC. Results: The measured quantity of BPA in the food grade oil was ranged between 0.5 to 4.37 µg/g of oil samples regardless of the date of production, the Batch Number, and the producing company. Statistical analysis revealed that the difference of BPA content in oil samples did not depend on their production date. Conclusion: According to the amount of allowable migration introduced by European committee, the amount of BPA migration and consequently contamination of almost all tested samples exceeds SML. Considering the toxic effects reported especially in fetus and young children, prompt regulatory interference is needed in this area.

Migration and health risks of nonylphenol and bisphenol a in soil-winter wheat systems with long-term reclaimed water irrigation

Reclaimed water reuse has become an important means of alleviating agricultural water shortage worldwide. However, the presence of endocrine disrupters has roused up considerable attention. Barrel test in farmland was conducted to investigate the migration of nonylphenol (NP) and bisphenol A (BPA) in soil-winter wheat system simulating reclaimed water irrigation. Additionally, the health risks on humans were assessed based on US EPA risk assessment model. The migration of NP and BPA decreased from the soil to the winter wheat; the biological concentration factors (BCFs) of NP and BPA in roots, stems, leaves, and grains all decreased with their added concentrations in soils. The BCFs of NP and BPA in roots were greatest (0.60–5.80 and 0.063–1.45, respectively). The average BCFs of NP and BPA in winter wheat showed negative exponential relations to their concentrations in soil. The amounts of NP and BPA in soil-winter wheat system accounted for 8.99–28.24% and 2.35–4.95%, respectively, of the initial amounts added into the soils. The hazard quotient (HQ) for children and adults ranged between 10−6 and 1, so carcinogenic risks could be induced by ingesting winter wheat grains under long-term reclaimed water irrigation.

Fast and simple determination and exposure assessment of bisphenol A, phenol, p-tert-butylphenol, and diphenylcarbonate transferred from polycarbonate food-contact materials to food simulants

Polycarbonate (PC) plastics find extensive use in baby bottles, food storage containers, and various kitchen items. Possibly hazardous chemicals, bisphenol A (BPA), phenol, p-tert-butylphenol (TBP), and diphenylcarbonate (DPC), are source materials or by-products from PC production. Therefore, a fast and simple analytical method was developed to determine and assess the exposure of BPA, phenol, TBP, and DPC transferred from PC food-contact materials to four different food simulants (water, 4% acetic acid, 50% ethanol, and n-heptane) at different temperatures. The method was validated in terms of limit of detection (LOD) and quantification (LOQ), recovery, and precision for the detection of BPA, phenol, and TBP using HPLC-FLD and of DPC using HPLC-UV. BPA, phenol, TBP, and DPC concentrations transferred from 200 PC samples to food simulants were determined. The highest migration levels of BPA (54.3 μg L−1) and phenol (43.8 μg L−1) were found in 50% ethanol at 70 °C. TBP did not migrate to any simulant. DPC did not show any migration from PC samples into water and only migrated from a cup to 4% acetic acid at 70 °C and 100 °C, whereas migration occurred from several cups, ladles, spoons, and tongs to 50% ethanol and to n-heptane at 25 °C. Food simulants and temperature were the crucial factors for the migration of BPA and phenol from PC samples. Estimated daily intakes (EDIs), based on food consumption and food-type distribution factors, for BPA, phenol, and DPC were calculated to be 0.007, 0.001, and 2.5 × 10−4 μg kg−1 bw day−1, respectively.