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Analysis and testing of bisphenol A, bisphenol A diglycidyl ether and their derivatives in canned dog foods

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Abstract

An analytical method was developed for the simultaneous determination of bisphenol A (BPA), bisphenol A diglycidyl ether (BADGE) and their derivatives, BADGE·2H2O, BADGE·H2O, BADGE·HCl·H2O, BADGE·2HCl and BADGE·HCl, in canned animal food commodities using reversed-phase high-performance liquid chromatography (HPLC) with fluorescence detection. The samples were cleaned up using solid-phase extraction (SPE) with hydrophobic polystyrene–divinylbenzene (PS/DVB) copolymer sorbent. The performance characteristics confirmed that the method used was in accordance with the EU validation criteria. The recovery values ranged from 62 to 97%. The repeatability (CVr) and within-laboratory reproducibility (CVW) values ranged from 2.3 to 9.7% and from 2.8 to 10.8%, respectively, while the limit of detection (LOD) and the limit of quantification (LOQ) values ranged from 5 to 10 µg/kg and from 5 to 15 µg/kg, respectively. The method was successfully used to evaluate the levels of 7 bisphenols in 24 of the canned dog foods retailed on the Slovenian market. BADGE·2H2O was found in all the samples tested, with values ranging from 16 to 540 µg/kg, while BPA was found in 96% of the samples tested and ranged from <5 to 208 µg/kg. The contribution of BADGE·H2O and BADGE·HCl·H2O was minor, while no traces of BADGE, BADGE·2HCl or BADGE·HCl were detected. Epoxy phenolic coatings were identified in the cans tested by the Fourier transform infrared spectroscopy (FTIR) analysis. Given the temporary human tolerable daily intake (TDI) value of 4 µg/kg b.w./day recently laid down by the European Food Safety Authority (EFSA), these results, especially those for the BPA in canned dog foods, merit further attention and investigation.

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References

  1. Michałowicz J (2014) Bisphenol A – sources, toxicity and biotransformation. Environ Toxicol Pharm 37:738–758

    Article  Google Scholar 

  2. Poole A, van Herwijnen P, Weideli H, Thomas MC, Ransbotyn G, Vance C (2004) Review of the toxicology, human exposure and safety assessment for bisphenol A diglycidylether (BADGE). Food Addit Contam 21(9):905–919

    Article  CAS  Google Scholar 

  3. Stroheker T, Picard K, Lhuguenot JC, Canivenc-Lavier MC, Chagnon MC (2004) Steroid activities comparison of natural and food wrap compounds in human breast cancer cell lines. Food Chem Toxicol 42:887–897

    Article  CAS  Google Scholar 

  4. Climie IJG, Hutson DH, Stoydin G (1981) Metabolism of the epoxy resin component 2,2-bis[4-(2,3-epoxypropoxy)phenyl]propane, the diglycidyl ether of bisphenol A (DGEBPA) in the mouse. Part II. Identification of metabolites in urine and faeces following a single oral dose of 14C-DGEBPA. Xenobiotica 11(6):401–424

    Article  CAS  Google Scholar 

  5. Satoh K, Ohyama K, Aoki N, Iida M, Nagai F (2004) Study on anti-androgenic effects of bisphenol a diglycidyl ether (BADGE), bisphenol F diglycidyl ether (BFDGE) and their derivatives using cells stably transfected with human androgen receptor, AR-EcoScreen. Food Chem Toxicol 42:983–993

    Article  CAS  Google Scholar 

  6. Nakazawa H, Yamaguchi A, Inoue K, Yamazaki T, Kato K, Yoshimura Y, Makino T (2002) In vitro assay of hydrolysis and chlorohydroxy derivatives of bisphenol A diglycidyl ether for estrogenic activity. Food Chem Toxicol 40:1827–1832

    Article  CAS  Google Scholar 

  7. Garcia RS, Losada PP (2004) Determination of bisphenol A diglycidyl ether and its hydrolysis and chlorohydroxy derivatives by liquid chromatography–mass spectrometry. J Chromatogr A 1032:37–43

    Article  Google Scholar 

  8. EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (2015) Scientific Opinion on the risks to public health related to the presence of bisphenol A (BPA) in foodstuffs: executive summary. EFSA J 13(1):3978, 23 pp. doi:10.2903/j.efsa.2015.3978

  9. Commission of the European Union (2005) Commission Regulation (EC) No 1895/2005 of 18 November 2005 on the restriction of use of certain epoxy derivatives in materials and articles intended to come into contact with food. Off J Eur Union L 302:28–32

    Google Scholar 

  10. Wooten KJ, Smith PN (2013) Canine toys and training devices as sources of exposure to phthalates and bisphenol A: quantitation of chemicals in leachate and in vitro screening for endocrine activity. Chemosphere 93:2245–2253

    Article  CAS  Google Scholar 

  11. Kang J-H, Kondo F (2002) Determination of bisphenol A in canned pet foods. Res Vet Sci 73:177–182

    Article  CAS  Google Scholar 

  12. Yonekubo J, Hayakawa K, Sajiki J (2008) Concentrations of bisphenol A, bisphenol A diglycidyl ether, and their derivatives in canned foods in Japanese markets. J Agric Food Chem 56:2041–2047

    Article  CAS  Google Scholar 

  13. Petersen H, Biereichel A, Burseg K, Simat TJ, Steinhart H (2008) Bisphenol A diglycidyl ether (BADGE) migrating from packaging material ‘disappears’ in food: reaction with food components. Food Addit Contam 25(7):911–920

    Article  CAS  Google Scholar 

  14. Coulier L, Bradley EL, Bas RC, Verhoeckx KCM, Driffield M, Harmer N, Castle L (2010) Analysis of reaction products of food contaminants and ingredients: bisphenol A diglycidyl ether (BADGE) in canned foods. J Agric Food Chem 58:4873–4882

    Article  CAS  Google Scholar 

  15. Goodson A, Summerfield W, Cooper I (2002) Survey of bisphenol A and bisphenol F in canned foods. Food Addit Contam 19(8):796–802

    Article  CAS  Google Scholar 

  16. Munguía-López EM, Soto-Valdez H (2001) Effect of heat processing and storage time on migration of bisphenol A (BPA) and bisphenol A-diglycidyl ether (BADGE) to aqueous food simulant from Mexican can coatings. J Agric Food Chem 49:3666–3671

    Article  Google Scholar 

  17. Munguía-López EM, Gerardo-Lugo S, Peralta E, Bolumen S, Soto-Valdez H (2005) Migration of bisphenol A (BPA) from can coatings into a fatty-food simulant and tuna fish. Food Addit Contam 22(9):892–898

    Article  Google Scholar 

  18. Hammarling L, Gustavsson H, Svensson K, Oskarsson A (2000) Migration of bisphenol-A diglycidyl ether (BADGE) and its reaction products in canned foods. Food Addit Contam 17(11):937–943

    Article  CAS  Google Scholar 

  19. Errico S, Bianco M, Mita L, Migliaccio M, Rossi S, Nicolucci C, Menale C, Portaccio M, Gallo P, Mita DG, Diano N (2014) Migration of bisphenol A into canned tomatoes produced in Italy: dependence on temperature and storage conditions. Food Chem 160:157–164

    Article  CAS  Google Scholar 

  20. Summerfield W, Goodson A, Cooper I (1998) Survey of bisphenol A diglycidyl ether (BADGE) in canned foods. Food Addit Contam 15(7):818–830

    Article  CAS  Google Scholar 

  21. Biles JE, White KD, McNeal TP, Begley TH (1999) Determination of the diglycidyl ether of bisphenol A and its derivatives in canned foods. J Agric Food Chem 47:1965–1969

    Article  CAS  Google Scholar 

  22. Simoneau C, Theobald A, Hannaert P, Roncari P, Roncari A, Rudolph T, Anklam E (1999) Monitoring of bisphenol-A-diglycidyl-ether (BADGE) in canned fish in oil. Food Addit Contam 16(5):189–195

    Article  CAS  Google Scholar 

  23. Berger U, Oehme M, Girardin L (2001) Quantification of derivatives of bisphenol A diglycidyl ether (BADGE) and novolac glycidyl ether (NOGE) migrated from can coatings into tuna by HPLC/fluorescence and MS detection. Fresh J Anal Chem 369(2):115–123

    Article  CAS  Google Scholar 

  24. Petersen H, Schaefer A, Buckow CA, Simat TJ, Steinhart H (2003) Determination of bisphenol A diglycidyl ether (BADGE) and its derivatives in food: identification and quantification by internal standard. Eur Food Res Technol 216:355–364

    Article  CAS  Google Scholar 

  25. Leepipatpiboon N, Sae-Khow O, Jayanta S (2005) Simultaneous determination of bisphenol-A-diglycidyl ether, bisphenol-F-diglycidyl ether, and their derivatives in oil-in-water and aqueous-based canned foods by high-performance liquid chromatography with fluorescence detection. J Chromatogr A 1073:331–339

    Article  CAS  Google Scholar 

  26. Sun C, Leong LP, Barlow PJ, Chan SH, Bloodworth BC (2006) Single laboratory validation of a method for the determination of bisphenol A, bisphenol A diglycidyl ether and its derivatives in canned foods by reversed-phase liquid chromatography. J Chromatogr A 1129:145–148

    Article  CAS  Google Scholar 

  27. Cao X, Dufresne G, Clement G, Bélisle S, Robichaud A, Beraldin F (2009) Levels of bisphenol A diglycidyl ether (BADGE) and bisphenol F diglycidyl ether (BFDGE) in canned liquid infant formula products in Canada and dietary intake estimates. J AOAC Int 92(6):1780–1789

    CAS  Google Scholar 

  28. Zhang H, Xue M, Lu Y, Dai Z, Wang H (2010) Microwave-assisted extraction for the simultaneous determination of Novolac glycidyl ethers, bisphenol A diglycidyl ether, and its derivatives in canned food using HPLC with fluorescence detection. J Sep Sci 33:235–243

    Article  CAS  Google Scholar 

  29. Lapviboonsuk J, Leepipatpiboon N (2014) A simple method for the determination of bisphenol A diglycidyl ether and its derivatives in canned fish. Anal Methods 6:5666–5672

    Article  CAS  Google Scholar 

  30. Maragou NC, Lampi EN, Thomaidis NS, Koupparis MA (2006) Determination of bisphenol A in milk by solid phase extraction and liquid chromatography–mass spectrometry. J Chromatogr A 1129:165–173

    Article  CAS  Google Scholar 

  31. Pardo O, Yusà V, León N, Pastor A (2006) Determination of bisphenol diglycidyl ether residues in canned foods by pressurized liquid extraction and liquid chromatography–tandem mass spectrometry. J Chromatogr A 1107:70–78

    Article  CAS  Google Scholar 

  32. Míguez J, Herrero C, Quintás L, Rodríguez C, Gigosos PG, Mariz OC (2012) 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 + NH4]+ aducts. Food Chem 135:1310–1315

    Article  Google Scholar 

  33. Bierdermann M, Grob K, Böhler P, Widmer HR (1998) Identification of migrants from coatings of food cans and tubes: reaction products of bisphenol-A-diglycidyl ether (BADGE) with phenols and solvents. Mitt Gebiete Lebensm Hyg 89:529–547

    Google Scholar 

  34. Salafranca J, Batlle R, Nerin C (1999) Use of solid-phase microextraction for the analysis of bisphenol A and bisphenol A diglycidyl ether in food simulants. J Chromatogr A 864:137–144

    Article  CAS  Google Scholar 

  35. Uematsu Y, Hirata K, Suzuki K, Iida K, Saito K (2001) Chlorohydrins of bisphenol A diglycidyl ether (BADGE) and of bisphenol F diglycidyl ether (BFDGE) in canned foods and ready-to-drink coffees from the Japanese market. Food Addit Contam 18(2):177–185

    Article  CAS  Google Scholar 

  36. Brede C, Skjevrak I, Herikstad H, Anensen E, Austvoll R, Hemmingsen T (2002) Improved sample extraction and clean-up for the GC–MS determination of BADGE and BFDGE in vegetable oil. Food Addit Contam 19(5):483–491

    Article  CAS  Google Scholar 

  37. Geens T, Apelbaum TZ, Goeyens L, Neels H, Covaci A (2010) Intake of bisphenol A from canned beverages and foods on the Belgian market. Food Addit Contam 27(11):1627–1637

    Article  CAS  Google Scholar 

  38. Zhang H, Xue M, Zou Y, Dai Z, Lin K (2010) Simultaneous determination of NOGE-related and BADGE-related compounds in canned food by ultra-performance liquid chromatography–tandem mass spectrometry. Anal Bioanal Chem 398:3165–3174

    Article  CAS  Google Scholar 

  39. Edinboro CH, Scott-Moncrieff JC, Janovitz E, Thacker HL, Glickman LT (2004) Epidemiologic study of relationships between consumption of commercial canned food and risk of hyperthyroidism in cats. J Am Vet Med Assoc 224:879–886

    Article  Google Scholar 

  40. Schecter A, Malik N, Haffner D, Smith S, Harris TR, Paepke O, Birnbaum L (2010) Bisphenol A (BPA) in U.S. Food Environ Sci Technol 44:9425–9430

    CAS  Google Scholar 

  41. Commission of the European Community (2002) Commission Decision 2002/657/EC of 12 August 2002 implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Off J Eur Commun L 221:8–36

    Google Scholar 

  42. Deceuninck Y, Bichon E, Durand S, Bemrah N, Zendong Z, Morvan ML, Marchand P, Dervilly-Pinel G, Antignac JP, Leblanc JC, Le Bizec B (2014) Development and validation of a specific and sensitive gas chromatography tandem mass spectrometry method for the determination of bisphenol A residues in a large set of food items. J Chromatogr A 1362:241–249

    Article  CAS  Google Scholar 

  43. AFFINISEP (2015) Determination of bisphenol A in canned food (vegetable). Application notebook for solid phase extraction, p 53. Available at: www.affinisep.com. Accessed 09 Aug 2016

  44. Uematsu Y, Hirata K, Iida K, Saito K (2000) Bisphenol A diglycidyl ether (BADGE) and related compounds in fish products packed in cans or multilayer laminated film packages from the Japanese market. J Food Hyg Soc Jpn 41(1):23–29

    Article  CAS  Google Scholar 

  45. Bemrah N, Jean J, Rivière G, Sanaa M, Leconte S, Bachelot M, Deceuninck Y, Le Bizec B, Dauchy X, Roudot A-C, Camel V, Grob K, Feidt C, Picard-Hagen N, Badot P-M, Foures F, Leblanc J-C (2014) Assessment of dietary exposure to bisphenol A in the French population with a special focus on risk characterisation for pregnant French women. Food Chem Toxicol 72:90–97

    Article  CAS  Google Scholar 

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Acknowledgements

This work was financed by the Slovenian Research Agency (ARRS) within the framework of the P4-0092 Research Program. The authors would like to express their gratitude to Irena Mubi, Vilma Lindner, Jurij Omahen, Benjamin Cerk and Gregor Frelih for their valued assistance.

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Authors and Affiliations

  1. Veterinary Faculty, University of Ljubljana, Gerbičeva Ulica 60, 1000, Ljubljana, Slovenia

    V. Cerkvenik-Flajs, M. Gombač & T. Švara

  2. Faculty of Mechanical Engineering, University of Maribor, Smetanova Ulica 17, 2000, Maribor, Slovenia

    J. Volmajer Valh

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  1. V. Cerkvenik-Flajs
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Cerkvenik-Flajs, V., Volmajer Valh, J., Gombač, M. et al. Analysis and testing of bisphenol A, bisphenol A diglycidyl ether and their derivatives in canned dog foods. Eur Food Res Technol 244, 43–56 (2018). https://doi.org/10.1007/s00217-017-2930-2

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  • DOI: https://doi.org/10.1007/s00217-017-2930-2

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