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Trends for the management of hazardous substances derived from fatty acids

지방산 유래 유해물질 관리 동향

  • 신재욱 (한국식품산업협회 부설 한국식품과학연구원) ;
  • 장길웅 (한국식품산업협회 부설 한국식품과학연구원)
  • Received : 2022.02.10
  • Accepted : 2022.03.14
  • Published : 2022.03.30

Abstract

More than 500 different compounds have been identified in the cooking process of frying oil as a result of chemical reactions such as oxidation, polymerization, hydrolysis and pyrolysis, 3-MCPDe(3-Monochloropropane -1,2-diol ester) and GE(glycidyl ester) are also included in these compounds. When MCPDe and GE derivatives are absorbed into the body, they are converted into free forms by lipase enzymes, which turn into 3-MCPD and glycidol(2,3-epoxy-1-propanol), respectively. These exhibit genotoxic and carcinogenic effects. As the toxicity of 3-MCPDe and GE is known worldwide, the health risk is being researched. However, regulations have not been established in countries other than the European Union(EU). Several studies for the analysis of 3-MCPDe and GE are being conducted, and direct methods and indirect methods are applied. As a result of analyzing 3-MCPDe and GE contained in commercially available foods by various analysis methods, the content of 3-MCPDe in baby food/infant formula was ND~600 ㎍/mL and GE was ND~750 ㎍/mL. and purified vegetable oils and fats showed <250-8,430 ㎍/mL and 1,880-9,530 ㎍/mL. Thus, 3-MCPDe and GE were detected in various food types, several studies for the reduction of 3-MCPDe and GE are being conducted around the world.

Keywords

References

  1. Abd Razak RA, Kuntom A, Siew WL, Ibrahim NA, Ramli MR, Hussein R, Nesaretnam K. Detection and monitoring of 3-monochloropropane-1,2-diol (3-MCPD) esters in cooking oils. Food Contr. 25:355-360 (2012) https://doi.org/10.1016/j.foodcont.2011.10.058
  2. Arisseto AP, Silva WC, Scaranelo GR, Vicente E. 3-MCPD and glycidyl esters in infant formulas from the Brazilian market: occurrence and risk assessment. Food Contr. 77: 76-81 (2017) https://doi.org/10.1016/j.foodcont.2017.01.028
  3. Blumhorst MR, Venkitasubramanian P Collison MW. Direct determination of glycidyl esters of fatty acids in vegetable oils by LC-MS. J. Am. Oil Chem. Soc. 88: 1275-1283 (2011) https://doi.org/10.1007/s11746-011-1873-1
  4. CODEX.Code of practice forthe reduction of 3-monochloropropane1,2-diol esters (3-MCPDEs) and glycidyl esters (GEs) in refined oils and food products made with refined oils (2019)
  5. Collison MW, Blumhorst M. Advances in LC-MS analysis of glycidyl esters. in: 102nd AOCS Annual Meeting & Expo. May 1-4, Cincinnati, OH, USA (2011)
  6. Crews C, Chiodini A, Granvogl M, Hamlet C, Hrncirik K, Kuhlmann, J, Lampen A, Scholz G, Weisshaar R, Wenzl T, Jatsi PR, Seefelder W. Analytical approaches for MCPD esters and glycidyl esters in food and biological samples: a review and future perspectives. Food Addit. Contam. Part A Chem. Anal. Control. Expo. Risk Assess. 30: 11-45 (2013) https://doi.org/10.1080/19440049.2012.720385
  7. Cui X, Zhang L, Yang D, Li J, Liu Q, Sui H, Liu Z, Zhou P. Occurrence of 3-and 2-monochloropropanediol esters in infant formulas in China and exposure assessment. Food Addit. Contam. Part A Chem. Anal. Control. Expo. Risk Assess. 38 1470-1480 (2021). https://doi.org/10.1080/19440049.2021.1925164
  8. Deutsche Gesellschaft fur Fettwissenschaft (DGF). DGF Standard Method C III 18 (09) - Determination of ester-bound 3-chloropropane-1,2-diol (3-MCPD esters) and 3-MCPD forming substances in fats and oils by means of GC-MS (2009).
  9. Deutsche Gesellschaft fur Fettwissenschaft (DGF). DGF Standard Method C-VI 18 (10) Fatty-acid-bound 3-chloropropane-1,2-diol (3-MCPD) and 2,3-epoxipropane-1-ol (glycidol). Determination in oils and fats by GC/MS (Differential measurement) (2011a).
  10. Deutsche Gesellschaft fur Fettwissenschaft (DGF). DGF Standard Method C-VI 17 (10) Ester-bound 3-chloropropane-1,2-diol (3-MCPD ester) and glycidol (glycidyl ester). Summation method for the determination in fats and oils by GC-MS (2011b).
  11. Divinova V, Svejkovska B, Dolezal M, Velisek J. Determination of free and bound 3-chloropropane-1,2-diol by gas chromatography with mass spectrometric detection using deuterated 3-chloropropane1,2-diol as internal standard. Czech J. Food Sci. 22: 182-189 (2004) https://doi.org/10.17221/3422-cjfs
  12. Dubois M, Tarres A, Goldmann T, Loeffelmann G, Donaubauer A, Seefelder W. Determination of seven glycidyl esters in edible oils by gel permeation chromatography extraction and liquid chromatography coupled to mass spectrometry detection. J. Agric. Food. Chem. 59: 12291-12301 (2011) https://doi.org/10.1021/jf2028347
  13. Dubois M. Analysis of MCPD and glycidyl-esters in edible oils. in: 102nd AOCS Annual Meeting & Expo. May 1-4, Cincinnati, OH, USA (2011)
  14. EFSA Risks for human health related to the presence of 3-and 2- monochloropropanediol (MCPD), and their fatty acid esters, and glycidyl fatty acid esters in food (2016)
  15. Ermacora A, Hrncirik K. Evaluation of an improved indirect method for the analysis of 3-MCPD esters based on acid transesterification. J. Am. Oil Chem. Soc. 89: 211-217 (2012a) https://doi.org/10.1007/s11746-011-1911-z
  16. Ermacora A, Hrncirik K. Indirect determination of 2-/3-MCPD and glycidyl esters in oils/fats: a new method based on acid transesterification. in: 102nd AOCS Annual Meeting & Expo. May 1-4, Cincinnati, OH, USA (2012b)
  17. European Commission Regulation. Proficiency test on the determination of 3-MCPD esters in edible oil (2010)
  18. European Commission Regulation. Maximum levels of 3-MCP, 3-MCPD fatty acid esters and glycidyl fatty acid esters in food (2020)
  19. FDA. Guidance Levels for 3-MCPD(3-chloro-1,2-propanediol) in AcidHydrolyzed Protein and Asian-Style Sauces (2008)
  20. Goh KM, Wong YH, Abas F, Lai OM, Cheong LZ, Wang Y, Tan CP. Effects of shortening and baking temperature on quality, MCPD ester and glycidyl ester content of conventional baked cake. Lebensm. Wiss. Technol. 116: 108553 (2019a) https://doi.org/10.1016/j.lwt.2019.108553
  21. Goh KM, Wong YH, Ang MY, Yeo SCM, Abas F, Lai OM, Tan CP. Comparison assessment between SIM and MRM mode in the analysis of 3-MCPD ester, 2-MCPD ester and glycidyl ester. Food Res. Int. 121: 553-560 (2019b) https://doi.org/10.1016/j.foodres.2018.12.013
  22. Goh KM, Wong YH, Tan CP, Nyam KL. A summary of 2-, 3-MCPD esters and glycidyl ester occurrence during frying and baking processes. Curr. Res. Food Sci. 4: 460-469 (2021) https://doi.org/10.1016/j.crfs.2021.07.002
  23. Granvogl M, Schieberle P. Quantitation of glycidyl esters via stable isotope dilution analysis. in: 102nd AOCS Annual Meeting & Expo. May 1-4, Cincinnati, OH, USA (2011)
  24. Haines TD, Adlaf KJ, Pierceall RM, Lee I, Venkitasubramanian P, Collison MW. Direct determination of MCPD fatty acid esters and glycidyl fatty acid esters in vegetable oils by LC-TOFMS. J. Am. Oil Chem. Soc. 88: 1-14 (2011). https://doi.org/10.1007/s11746-010-1732-5
  25. Hamlet CG, Sadd PA. Chloropropanols and their esters in cereal products. Czech J. Food Sci. 22: 259-262 (2004)
  26. Health Canada. Maximum Levels for Chemical Contaminants in Foods (2007)
  27. Hori K, Koriyama N, Omori H, Kuriyama M, Arishima T, Tsumura, K. Simultaneous determination of 3-MCPD fatty acid esters and glycidol fatty acid esters in edible oils using liquid chromatography time-of-flight mass spectrometry. LWT. 48: 204-208 (2012) https://doi.org/10.1016/j.lwt.2012.03.014
  28. Hrncirik K, Zelinkova Z, Ermacora A. Critical factors of indirect determination of 3-chloropropane-1,2-diol esters. Eur. J. Lipid Sci. Technol. 113: 361-367 (2011) https://doi.org/10.1002/ejlt.201000316
  29. Huang Z, Xie D, Cao Z, Guo Z, Chen L, Jiang L, Sui X, Wang Z. The effects of chloride and the antioxidant capacity of fried foods on 3-chloro-1, 2-propanediol esters and glycidyl esters during long-term deep-frying. LWT. 145: 111511. (2021) https://doi.org/10.1016/j.lwt.2021.111511
  30. Jedrkiewicz R, Glowacz A, Gromadzka J, Namiesnik J. Determination of 3-MCPD and 2-MCPD esters in edible oils, fish oils and lipid fractions of margarines available on Polish market. Food Contr. 59: 487-492 (2016) https://doi.org/10.1016/j.foodcont.2015.05.039
  31. Kalkan O, Topkafa M, Kara, H. Determination of effect of some parameters on formation of 2-monochloropropanediol, 3-monochloropropanediol and glycidyl esters in the frying process with sunflower oil, by using central composite design. J. Food Compost. Anal. 96: 103681 (2021) https://doi.org/10.1016/j.jfca.2020.103681
  32. Kuhlmann J. Determination of bound 2,3-epoxy-1-propanol(glycidol) and bound monochloropropanediol (MCPD) in refined oils. Eur. J. Lipid Sci. Technol. 113: 335-344 (2011) https://doi.org/10.1002/ejlt.201000313
  33. MacMahon S, Begley T, Diachenko G. LC-MS/MS detection of glycidyl esters and 3-MCPD esters in edible oils. in: 102nd AOCS Annual Meeting & Expo. May 1-4, Cincinnati, OH, USA (2011)
  34. MacMahon S, Begley TH, Diachenko GW. Occurrence of 3-MCPD and glycidyl esters in edible oils in the United States. Food Addit. Contam. Part A Chem. Anal. Control. Expo. Risk Assess. 30: 2081-2092 (2013) https://doi.org/10.1080/19440049.2013.840805
  35. MAFF (Ministry of Agriculture, Forestry and Fisheries). Domestic measures to reduce chloropropanols and related substances in food. (in japanese) Available from: http://www.maff.go.jp/j/syouan/seisaku/c_propanol/program_japan.html. Accessed Sep. 17, 2021.
  36. Masukawa Y, Shiro H, Kondo N, Kudo N. Generalized method to quantify glycidol fatty acid esters in edible oils. J. Am. Oil Chem. Soc. 88: 15-21 (2011) https://doi.org/10.1007/s11746-010-1645-3
  37. Miyazaki K, Koyama K, Sasako H, Hirao T. Indirect method for simultaneous determinations of 3-chloro-1,2-propanediol fatty acid esters and glycidyl fatty acid esters. J. Am. Oil Chem. Soc. 89:1403-1407 (2012) https://doi.org/10.1007/s11746-012-2047-5
  38. Moravcova E, Vaclavik L, Lacina O, Hrbek V, Riddellova K, Hajslova J. Novel approaches to analysis of 3-chloropropane-1,2-diol esters in vegetable oils. Anal. Bioanal. Chem. 402: 2871-2888 (2012) https://doi.org/10.1007/s00216-012-5732-1
  39. Nguyen KH, Fromberg A. Monochloropropanediol and glycidyl esters in infant formula and baby food products on the Danish market: occurrence and preliminary risk assessment. Food Contr. 110: 106980 (2020) https://doi.org/10.1016/j.foodcont.2019.106980
  40. Pinkston JD, Stoffolano PJ. Update on the development of a sensitive, accurate, and user-friendly method for the direct determination of 3-MCPD esters. in: 102nd AOCS Annual Meeting & Expo. May 1-4, Cincinnati, OH, USA (2011)
  41. Seefelder W, Varga N, Studer A, Williamson G, Scanlan FP and Stadler RH. Esters of 3-chloro-1,2-propanediol (3-MCPD) in vegetable oils: significance in the formation of 3-MCPD. Food Addit. Contam A, 25: 391-400 (2008) https://doi.org/10.1080/02652030801920582
  42. Shimamura Y, Inagaki R, Oike M, Dong B, Gong W, Masuda S. Glycidol fatty acid ester and 3-monochloropropane-1, 2-diol fatty acid ester in commercially prepared foods. Foods, 10: 2905 (2021). https://doi.org/10.3390/foods10122905
  43. Shiro H, Kondo N, Kibune N, Masukawa Y. Direct method for quantification of glycidol fatty acid esters in edible oils. Eur. J. Lipid Sci. Technol. 113: 356-360 (2011a) https://doi.org/10.1002/ejlt.201000395
  44. Shiro H, Kondo N, Masukawa Y. Validation of quantitative method for glycidol fatty acid esters (GEs) in edible oils. in: 102nd AOCS Annual Meeting & Expo. May 1-4, Cincinnati, OH, USA (2011b)
  45. Spungen JH, MacMahon S, Leigh J, Flannery B, Kim G, Chirtel S, Smegal D. Estimated US infant exposures to 3-MCPD esters and glycidyl esters from consumption of infant formula. Food Addit. Contam. Part A Chem. Anal. Control. Expo. Risk Assess. 35: 1085-1092 (2018) https://doi.org/10.1080/19440049.2018.1459051
  46. Tiong SH, Nair A, Abd. Wahid SA, Saparin N, Ab. Karim NA, Ahmad Sabri MP. Md. Zain MZ, The HF, Adni AS, Tan CP, Lai OM, Cheah SS, Appleton DR. Palm oil supply chain factors impacting chlorinated precursors of 3-MCPD esters. Food Addit. Contam. Part A Chem. Anal. Control. Expo. Risk Assess. 38: 2012-2025 (2021) https://doi.org/10.1080/19440049.2021.1960430
  47. Wang L, Ying Y, Hu Z, Wang T, Shen X, Wu P. Simultaneous determination of 2-and 3-MCPD esters in infant formula milk powder by solid-phase extraction and GC-MS analysis. J. AOAC Int. 99: 786-791 (2016) https://doi.org/10.5740/jaoacint.15-0310
  48. Xu M, Jin Z, Yang Z, Rao J, Chen B. Optimization and validation of in-situ derivatization and headspace solid-phase microextraction for gas chromatography-mass spectrometry analysis of 3-MCPD esters, 2-MCPD esters and glycidyl esters in edible oils via central composite design. Food Chem. 307: 125542 (2020) https://doi.org/10.1016/j.foodchem.2019.125542
  49. Zelinkova Z, Dolezal M, Velisek J. Occurrence of 3-chloropropane-1,2-diol fatty acid esters in infant and baby foods. Eur. Food Res. Technol. 228:571-578 (2008) https://doi.org/10.1007/s00217-008-0965-0
  50. Zelinkova Z, Svejkovska B, Velisek J, Dolezal M. Fatty acid esters of 3-chloropropane-1,2-diol in edible oils. Food Addit. Contam. 23: 1290-1298 (2006) https://doi.org/10.1080/02652030600887628
  51. Zulkurnain M, Lai OM, Latip RA, Nehdi IA, Ling TC, Tan CP. The effects of physical refining on the formation of 3-monochloropropane-1,2-diol esters in relation to palm oil minor components. Food Chem. 135:799-805 (2012) https://doi.org/10.1016/j.foodchem.2012.04.144
  52. 식품의약품안전처. 2020 식품 등의 생산실적 통계 (2020)
  53. 식품의약품안전처. 식품의 기준 및 규격 제2020-3호 (2020)
  54. 식품의약품안전처. 식품 중 glycidyl ester 시험법 개발 및 오염실태조사 (2017)
  55. 식품의약품안전처. 식품 중 유해물질 관리의 관리 현황 (2007)
  56. 식품의약품안전처. 식품 중 지방산 유래 유해물질 위해성 연구 (2018)