The impact of infant formula production on the concentrations of 3-MCPD and glycidyl esters

References

• Abraham K, Appel KE, Berger-Preiss E, Apel E, Gerling S, Mielke H, Creutzenberg O, Lampen A. 2013. Relative oral bioavailability of 3-MCPD from 3-MCPD fatty acid esters in rats. Arch Toxicol. 87:649–659.
   PubMed Web of Science ®Google Scholar
• [AOCS] American Oil Chemists’ Socitey. 2017a. AOCS official method Cd 29a-13: 2- and 3-MCPD fatty acid esters and glycidol fatty acid esters in edible oils and fats by acid transesterification and GC/MS. In: Official methods and recommended practices of the AOCS. 7th ed. Urbana (IL): 1–18.
   Google Scholar
• (AOCS) American Oil Chemists’ Socitey. 2017b. AOCS official method Cd 29b-13: 2- and 3-MCPD fatty acid esters and glycidol fatty acid esters in edible oils and fats by alkaline transesterification and GC/MS. In: Official methods and recommended practices of the AOCS. 7th ed. Urbana (IL): 1–14.
   Google Scholar
• (AOCS) American Oil Chemists’ Socitey. 2017c. AOCS official method Cd 29c-13: 2- and 3-MCPD fatty acid esters and glycidol fatty acid esters in edible oils and fats by GC/MS (Difference method). In: Official methods and recommended practices of the AOCS. 7th ed. Urbana (IL): 1–14.
   Google Scholar
• Appel KE, Abraham K, Berger-Preiss E, Hansen T, Apel E, Schuchardt S, Vogt C, Bakhiya N, Creutzenberg O, Lampen A. 2013. Relative oral bioavailability of glycidol from glycidyl fatty acid esters in rats. Arch Toxicol. 87:1649–1659.
   PubMed Web of Science ®Google Scholar
• Bakhiya N, Abraham K, Gürtler R, Appel KE, Lampen A. 2011. Toxicological assessment of 3-chloropropane-1,2-diol and glycidol fatty acid esters in food. Mol Nutr Food Res. 55:509–521.
   PubMed Web of Science ®Google Scholar
• Becalski A, Zhao T, Feng S, Lau BPY. 2015. A pilot survey of 2- and 3-monochloropropanediol and glycidol fatty acid esters in baby formula on the Canadian market 2012–2013. J Food Compost Anal. 44:111–114.
   Web of Science ®Google Scholar
• Birch EE, Garfield S, Hoffman DR, Uauy R, Birch DG. 2000. A randomized controlled trial of early dietary supply of long-chain polyunsaturated fatty acids and mental development in term infants. Dev Med Child Neurol. 42:174–181.
   PubMed Web of Science ®Google Scholar
• Birch EE, Hoffman DR, Uauy R, Birch DG, Prestidge C. 1998. Visual acuity and the essentiality of docosahexaenoic acid and arachidonic acid in the diet of term infants. Pediatr Res. 44:201–209.
   PubMed Web of Science ®Google Scholar
• Blumhorst MR, Collison MW, Cantrill R, Shiro H, Masukawa Y, Kawai S, Yasunaga K. 2013. Collaborative study for the analysis of glycidyl fatty acid esters in edible oils using LC–MS. J Am Oil Chem Soc. 90:493–500.
   Web of Science ®Google Scholar
• Cheng W-W, Liu G-Q, Wang L-Q, Liu Z-S. 2017. Glycidyl fatty acid esters in refined edible oils: a review on formation, occurrence, analysis, and elimination methods. Compr Rev Food Sci F. 16:263–281.
   Google Scholar
• Cho W-S, Han BS, Nam KT, Park K, Choi M, Kim SH, Jeong J, Jang DD. 2008. Carcinogenicity study of 3-monochloropropane-1,2-diol in Sprague–dawley rats. Food Chem Toxicol. 46:3172–3177.
   PubMed Web of Science ®Google Scholar
• Craft BD, Nagy K. 2012. Mitigation of MCPD-ester and glycidyl-ester levels during the production of refined palm oil. Lipid Tech. 24:155–157.
   Google Scholar
• Craft BD, Nagy K, Sandoz L, Destaillats F. 2012. Factors impacting the formation of monochloropropanediol (MCPD) fatty acid diesters during palm (Elaeis guineensis) oil production. Food Addit Contam Part A. 29:354–361.
   PubMed Web of Science ®Google Scholar
• Destaillats F, Craft BD, Sandoz L, Nagy K. 2012a. Formation mechanisms of monochloropropanediol (MCPD) fatty acid diesters in refined palm (Elaeis guineensis) oil and related fractions. Food Addit Contam Part A. 29:29–37.
   PubMed Web of Science ®Google Scholar
• Destaillats FD, Craft B, Dubois M, Nagy K. 2012b. Glycidyl esters in refined palm (Elaeis guineensis) oil and related fractions. Part I: formation mechanism. Food Chem. 131:1391–1398.
   Web of Science ®Google Scholar
• Dubois M, Empl A-M, Jaudzems G, Basle Q, Konings E. 2019. Determination of 2- and 3-MCPD as well as 2- and 3-MCPD esters and Glycidyl Esters (GE) in infant and adult/pediatric nutritional formula by gas chromatography coupled to mass spectrometry method, first action 2018.03. J AOAC Int. 102. doi:10.5740/jaoacint.18-0266.
   PubMed Web of Science ®Google Scholar
• Dubois M, Tarres A, Goldmann T, Empl AM, Donaubauer A, Seefelder W. 2012. Comparison of indirect and direct quantification of esters of monochloropropanediol in vegetable oil. J Chromatogr A. 1236:189–201.
   PubMed Web of Science ®Google Scholar
• [EFSA CONTAM] European Food Safety Authority Panel on Contaminants in the Food Chain. 2016. 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. Efsa J. 14:1–159.
   Web of Science ®Google Scholar
• [EFSA CONTAM] European Food Safety Authority Panel on Contaminants in the Food Chain. 2018. Update of the risk assessment on 3-monochloropropanediol and its fatty acid esters. Efsa J. 16:1583.
   Web of Science ®Google Scholar
• Ermacora A, Hrncirik K. 2013. A novel method for simultaneous monitoring of 2-MCPD, 3-MCPD and glycidyl esters in oils and fats. J Am Oil Chem Soc. 90:1–8.
   Web of Science ®Google Scholar
• [FEDIOL] Federation for European Oil and Proteinmeal Industry. 2015. Report: MCPD esters and glycidyl esters: review of mitigation measures. Bussells, Belgium. http://www.fediol.be/data/FEDIOL%20Review%20of%20Mitigation%20Measures%20MCPD%20Esters%20and%20Glycidyl%20Esters%20-%2024%20June%202015.pdf.
   Google Scholar
• [FSCJ] Food Safety Commission of Japan. 2015. Considerations on glycidol and its fatty acid esters in foods. Risk assessment report - Novel Foods and Food Additives FS/185/2015, Japan. http://www.fsc.go.jp/english/evaluationreports/others/annex_glycidol_26-52.pdf.
   Google Scholar
• [BLL] German Federation for Food Law and Food Science. 2016. Report: Toolbox for the Mitigation of 3-MCPD Esters and Glycidyl Esters in Food. Berlin (Germany). http://www.bll.de/de/infomaterial/toolboxen/pb-toolbox-3-mcpd-flycidyl-fe.
   Google Scholar
• Haines TD, Adlaf KJ, Pierceall RM, Lee I, Venkitasubramanian P, Collison MW. 2011. 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.
   PubMed Web of Science ®Google Scholar
• Hori K, Koriyama N, Omori H, Kuriyama M, Arishima T, Tsumura K. 2012. Simultaneous determination of 3-MCPD fatty acid esters and glycidol fatty acid esters in edible oils using liquid chromatography time-of-flight mass spectrometry. Food Sci Technol Int. 48:204–208.
   Web of Science ®Google Scholar
• Hrncirik K, van Duijn G. 2011. An initial study on the formation of 3-MCPD esters during oil refining. Eur J Lipid Sci Technol. 113:374–379.
   Web of Science ®Google Scholar
• Hrncirik K, Zelinkova Z, Ermacora A. 2011. Critical factors of indirect determination of 3-chloropropane-1,2-diol esters. Eur J Lipid Sci Technol. 113:361–367.
   Web of Science ®Google Scholar
• [IARC] International Agency for Research on Cancer. 2000. IARC monographs on some industrial chemicals: glycidol. Lyon, France. 77:469–486.
   Google Scholar
• [IARC] International Agency for Research on Cancer. 2016. IARC monographs on some chemicals present in industrial and consumer products, food and drinking water: 3-Monochloro-1,2-propanediol. Lyon, France. 101:349–374.
   Google Scholar
• [ISO] International Organization for Standardization. 2015. ISO 18363-1:2015: determination of fatty-acid-bound chloropropanediols (MCPDs) and glycidol by GC/MS; Part 1: method using fast alkaline transesterification and measurement for 3-MCPD and differential measurement for glycidol. Geneva (Switzerland): ISO Standards Catalogue.
   Google Scholar
• [ISO] International Organization for Standardization. 2017. ISO 18363-3:2017: determination of fatty-acid-bound chloropropanediols (MCPDs) and glycidol by GC/MS; Part 3: method using acid transesterification and measurement for 2-MCPD, 3-MCPD and glycidol. Geneva (Switzerland): ISO Standards Catalogue.
   Google Scholar
• [ISO] International Organization for Standardization. 2018. ISO 18363-2:2018: determination of fatty-acid-bound chloropropanediols (MCPDs) and glycidol by GC/MS; Part 2: method using slow alkaline transesterification and measurement for 2-MCPD, 3-MCPD and glycidol. Geneva (Switzerland): ISO Standards Catalogue.
   Google Scholar
• [JECFA] Joint FAO/WHO Expert Committee on Food Additives. 2017. WHO technical report series: eighty-third report of evaluation of certain contaminants in food: 3-MCPD esters and 3-MCPD. Geneva (Switzerland): World Health Organization (WHO) Press. 90–106.
   Google Scholar
• Kaze N, Sato H, Yamamoto H, Watanabe Y. 2011. Bidirectional conversion between 3-Monochloro-1,2-propanediol and glycidol in course of the procedure of DGF standard methods. J Am Oil Chem Soc. 88:1143–1151.
   Web of Science ®Google Scholar
• Kuhlmann J. 2011. Determination of bound 2,3-epoxy-1-propanol (glycidol) and bound monochloropropanediol (MCPD) in refined oils. Eur J Lipid Sci Technol. 113:335–344.
   Web of Science ®Google Scholar
• Kuhlmann J. 2019. 2-Monochloropropanediol (2-MCPD), 3-Monochloropropanediol (3-MCPD), and glycidol in infant and adult/pediatric nutritional formula: single-laboratory validation, first action 2018.12. J AOAC Int. 102:1205–1220.
   Web of Science ®Google Scholar
• Leigh JK, MacMahon S. 2016. Extraction and liquid chromatography–tandem mass spectrometry detection of 3-Monochloropropanediol esters and glycidyl esters in infant formula. J Agric Food Chem. 64:9442–9451.
   PubMed Web of Science ®Google Scholar
• Leigh JK, MacMahon S. 2017. Occurrence of 3-monochloropropanediol esters and glycidyl esters in commercial infant formulas in the United States. Food Addit Contam A. 34:356–370.
   PubMed Web of Science ®Google Scholar
• Lien EL, Richard C, Hoffman DR. 2018. DHA and ARA addition to infant formula: current status and future research directions. Prostaglandins Leukot Essent Fatty Acids. 128:26–40.
   PubMed Web of Science ®Google Scholar
• Liu M, Gao B-Y, Qin F, Wu -P-P, Shi H-M, Luo W, Ma A-N, Jiang Y-R, Xu X-B, Yu -L-L. 2012. Acute oral toxicity of 3-MCPD mono- and di-palmitic esters in Swiss mice and their cytotoxicity in NRK-52E rat kidney cells. Food Chem Toxicol. 50:3785–3791.
   PubMed Web of Science ®Google Scholar
• Łoś-Rycharska E, Kieraszewicz Z, Czerwionka-Szaflarska M. 2016. Medium chain triglycerides (MCT) formulas in paediatric and allergological practice. Prz Gastroenterol. 11:226–231.
   PubMed Web of Science ®Google Scholar
• MacMahon S, Begley TH, Diachenko GW. 2013a. Analysis of processing contaminants in edible oils. Part 2. Liquid chromatography–tandem mass spectrometry method for the direct detection of 3-Monochloropropanediol and 2-Monochloropropanediol diesters. J Agric Food Chem. 61:4748–4757.
   PubMed Web of Science ®Google Scholar
• MacMahon S, Begley TH, Diachenko GW. 2013b. Occurrence of 3-MCPD and glycidyl esters in edible oils in the United States. Food Addit Contam A. 30:2081–2092.
   PubMed Web of Science ®Google Scholar
• MacMahon S, Mazzola E, Begley TH, Diachenko GW. 2013c. Analysis of processing contaminants in edible oils. Part 1. Liquid chromatography–tandem mass spectrometry method for the direct detection of 3-monochloropropanediol monoesters and glycidyl esters. J Agric Food Chem. 61:4737–4747.
   PubMed Web of Science ®Google Scholar
• MacMahon S, Ridge CD, Begley TH. 2014. Liquid Chromatography–Tandem Mass Spectrometry (LC-MS/MS) method for the direct detection of 2-Monochloropropanediol (2-MCPD) esters in edible oils. J Agric Food Chem. 62:11647–11656.
   PubMed Web of Science ®Google Scholar
• Matthäus B, Pudel F. 2013. Mitigation of 3-MCPD and glycidyl esters within the production chain of vegetable oils especially palm oil. Lipid Tech. 25:151–155.
   Google Scholar
• Matthäus B, Pudel F, Fehling P, Vosmann K, Freudenstein A. 2011. Strategies for the reduction of 3-MCPD esters and related compounds in vegetable oils. Eur J Lipid Sci Technol. 113:380–386.
   Web of Science ®Google Scholar
• Mazzocchi A, D’Oria V, De Cosmi V, Bettocchi S, Milani GP, Silano M, Agostoni C. 2018. The role of lipids in human milk and infant formulae. Nutrients. 10:567.
   Web of Science ®Google Scholar
• Moravcova E, Vaclavik L, Lacina O, Hrbek V, Riddellova K, Hajslova J. 2012. Novel approaches to analysis of 3-chloropropane-1,2-diol esters in vegetable oils. Anal Bioanal Chem. 402:2871–2883.
   PubMed Web of Science ®Google Scholar
• Pudel F, Benecke P, Fehling P, Freudenstein A, Matthäus B, Schwaf A. 2011. On the necessity of edible oil refining and possible sources of 3-MCPD and glycidyl esters. Eur J Lipid Sci Technol. 113:368–373.
   Web of Science ®Google Scholar
• Stamatov SD, Stawinski J. 2005. Regioselective opening of an oxirane system with trifluoroacetic anhydride. A general method for the synthesis of 2-monoacyl- and 1,3-symmetrical triacylglycerols. Tetrahedron. 61:3659–3669.
   Web of Science ®Google Scholar
• Svejkovská B, Novotný O, Divinová V, Reblová Z, Doležal M, Velíšek J. 2004. Esters of 3-chloropropane-1,2-diol in foodstuffs. Czech J Food Sci. 22:190–196.
   Web of Science ®Google Scholar
• Weißhaar R. 2011. Fatty acid esters of 3-MCPD: overview of occurrence and exposure estimates. Eur J Lipid Sci Technol. 113:304–308.
   Web of Science ®Google Scholar
• Yamazaki K, Ogiso M, Isagawa S, Urushiyama T, Ukena T, Kibune N. 2013. A new, direct analytical method using LC-MS/MS for fatty acid esters of 3-chloro-1,2-propanediol (3-MCPD esters) in edible oils. Food Addit Contam A. 30:52–68.
   PubMed Web of Science ®Google Scholar
• Zelinková Z, Svejkovská B, Velíšek J, Doležal M. 2006. Fatty acid esters of 3-chloropropane-1,2-diol in edible oils. Food Addit Contam. 23:1290–1298.
   PubMed Web of Science ®Google Scholar
• Zwagerman R, Overman P. 2019. Optimized analysis of MCPD- and glycidyl esters in edible oils and fats using fast alkaline transesterification and 13C-correction for glycidol overestimation: validation including interlaboratory comparison. Eur J Lipid Sci Technol. 121:1800395.
   Web of Science ®Google Scholar