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(4):649–659. doi:https://doi.org/10.1007/s00204-012-0970-8.
- [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: American Oil Chemists’ Society.
- [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: American Oil Chemists’ Society.
- [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: American Oil Chemists’ Society.
- 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(9):1649–1659. doi:https://doi.org/10.1007/s00204-013-1061-1.
- Araujo M, Beekman JK, Mapa MST, MacMahon S, Zhao Y, Flynn TJ, Flannery B, Mossoba ME, Sprando RL. 2020. Assessment of intestinal absorption/metabolism of 3-chloro-1,2-propanediol (3-MCPD) and three 3-MCPD monoesters by Caco-2 cells. Toxicol In Vitro. 67:104887. doi:https://doi.org/10.1016/j.tiv.2020.104887.
- 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(4):509–521. doi:https://doi.org/10.1002/mnfr.201000550.
- 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. doi:https://doi.org/10.1016/j.jfca.2015.08.004.
- Beekman JK, Granvogl M, MacMahon S. 2019. Analysis and occurrence of MCPD and glycidyl esters in infant formulas and other complex food matrices. In: Food-borne toxicants: Formation, analysis, and toxicology. Washington (DC): American Chemical Society; p. 67–90.
- Beekman JK, Grassi K, MacMahon S. 2020. Updated occurrence of 3-monochloropropane-1,2-diol esters (3-MCPD) and glycidyl esters in infant formulas purchased in the United States between 2017 and 2019. Food Addit Contam A. 37(3):374–390. doi:https://doi.org/10.1080/19440049.2019.1706002.
- Beekman JK, MacMahon S. 2020. The impact of infant formula production on the concentrations of 3-MCPD and glycidyl esters. Food Addit Contam A. 37(1):48–60. doi:https://doi.org/10.1080/19440049.2019.1672898.
- 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(9):3172–3177. doi:https://doi.org/10.1016/j.fct.2008.07.003.
- [CAC] Codex Alimentarius Commission. 2018. Appendix VI: proposed draft code of practice for the reduction of 3-monochloropropane-1,2-diol esters (3-MCPDE) and Glycidyl Esters (GE) in Refined Oils and Food Products Made with Refined Oils: report of the 12th Session of the Codex Committee on Contaminants In Foods. 59–64. Utrecht (The Netherlands). http://www.fao.org/fao-who-codexalimentarius/sh-proxy/en/?lnk=1&url=https%253A%252F%252Fworkspace.fao.org%252Fsites%252Fcodex%252FMeetings%252FCX-735-12%252FREPORT%252520%2528FINAL%2529%252FREP18_CFe.pdf
- Craft BD, Nagy K. 2012. Mitigation of MCPD-ester and glycidyl-ester levels during the production of refined palm oil. Lipid Tech. 24(7):155–157. doi:https://doi.org/10.1002/lite.201200207.
- 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 A. 29:354–361.
- Destaillats F, Craft BD, Dubois M, Nagy K. 2012. Glycidyl esters in refined palm (Elaeis guineensis) oil and related fractions. Part I: Formation mechanism. Food Chem. 131:1391–1398.
- [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. Tokyo (Japan). http://www.fsc.go.jp/english/evaluationreports/others/annex_glycidol_26-52.pdf
- [FEDIOL] EU Vegetable Oil and Proteinmeal Industry. 2015. Report: MCPD esters and glycidyl esters: review of mitigation measures. Brussells (Belgium). http://www.fediol.be/data/FEDIOL%20Review%20of%20Mitigation%20Measures%20MCPD%20Esters%20and%20Glycidyl%20Esters%20-%2024%20June%202015.pdf
- [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.
- [BLL] German Federation for Food Law and Food Science. 2016. 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
- Destaillats F, Craft BD, Sandoz L, Nagy K. 2012. Formation mechanisms of Monochloropropanediol (MCPD) fatty acid diesters in refined palm (Elaeis guineensis) oil and related fractions. Food Addit Contam A. 29(1):29–37. doi:https://doi.org/10.1080/19440049.2011.633493.
- 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(3):903–914. doi:https://doi.org/10.5740/jaoacint.18-0266.
- [IARC] International Agency for Research on Cancer. 2000. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Some industrial chemicals. Lyon (France). 77:469–486.
- [ISO] International Organization for Standardization. 2015. ISO 18363-1:2015: Animal and vegetable fats and oils – 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.
- [IARC] International Agency for Research on Cancer. 2016. IARC monographs on the Evaluation of Carcinogenic Risks to Humans. Some Chemicals Present in Industrial and Consumer Products, Food and Drinking-Water Lyon (France). 101:349–374.
- [JECFA] Joint Food and Agriculture Organization (FAO)/World Health Organization (WHO) Expert Committee on Food Additives. 2016. Summary report of the eighty-third meeting of JECFA: JECFA/83/SC. Rome (Italy); pp. 5–7. http://www.fao.org/3/a-bq821e.pdf
- [ISO] International Organization for Standardization. 2017. ISO 18363-3:2017: Animal and vegetable fats and oils – 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.
- 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. doi:https://doi.org/10.1016/j.chroma.2012.03.009.
- [EC] European Commission. 2018. Commission Regulation (EU) 2018/290 of 26 February 2018 amending Regulation (EC) No 1881/2006 as regards maximum levels of glycidyl fatty acid esters in vegetable oils and fats, infant formula, follow-on formula and foods for special medical purposes intended for infants and young children. Brussels (Belgium). https://eur-lex.europa.eu/legal-content/EN/XT/PDF/?uri=CELEX:32018R0290&from=EN
- [ISO] International Organization for Standardization. 2018. ISO 18363-2:2018: Animal and Vegetable fats and oils – 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.
- [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.
- [EC] European Commission. 2020. Commission Regulation (EU) 2020/1322 of 23 September 2020 amending Regulation (EC) No 1881/2006 as regards maximum levels of 3-monochloropropanediol (3-MCPD), 3-MCPD fatty acid esters, and glycidyl fatty acid esters in certain foods Brussels (Belgium). https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=uriserv%3AOJ.L_.2020.310.01.0002.01.ENG&toc=OJ%3AL%3A2020%3A310%3ATOC
- 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):1–14. doi:https://doi.org/10.1007/s11746-010-1732-5.
- 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(3):374–379. doi:https://doi.org/10.1002/ejlt.201000317.
- 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(3):335–344. doi:https://doi.org/10.1002/ejlt.201000313.
- 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(4):1205–1220. doi:https://doi.org/10.5740/jaoacint.19-0026.
- 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(49):9442–9451. doi:https://doi.org/10.1021/acs.jafc.6b04361.
- 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(3):356–370. doi:https://doi.org/10.1080/19440049.2016.1276304.
- 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(10):3785–3791. doi:https://doi.org/10.1016/j.fct.2012.07.038.
- Liu M, Liu J, Wu Y, Gao B, Wu P, Shi H, Sun X, Huang H, Wang TT, Yu L. 2017. Preparation of five 3-MCPD fatty acid esters, and the effects of their chemical structures on acute oral toxicity in Swiss mice. J Sci Food Agric. 97(3):841–848. doi:https://doi.org/10.1002/jsfa.7805.
- MacMahon S, Begley TH, Diachenko GW. 2013a. Occurrence of 3-MCPD and glycidyl esters in edible oils in the United States. Food Addit Contam A. 30(12):2081–2092. doi:https://doi.org/10.1080/19440049.2013.840805.
- MacMahon S, Begley TH, Diachenko GW. 2013b. 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(20):4748–4757. doi:https://doi.org/10.1021/jf400581g.
- MacMahon S, Mazzola E, Begley TH, Diachenko GW. 2013. 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(20):4737–4747. doi:https://doi.org/10.1021/jf4005803.
- 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(48):11647–11656. doi:https://doi.org/10.1021/jf503994m.
- 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(7):151–155. doi:https://doi.org/10.1002/lite.201300288.
- Oey SB, van der Fels-Klerx HJ, Fogliano V, van Leeuwen SPJ. 2019. Mitigation strategies for the reduction of 2- and 3-MCPD esters and glycidyl esters in the vegetable oil processing industry. Compr Rev Food Sci Food Saf. 18(2):349–361. doi:https://doi.org/10.1111/1541-4337.12415.
- 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(3):368–373. doi:https://doi.org/10.1002/ejlt.201000460.
- Pudel F, Benecke P, Vosmann K, Matthäus B. 2016. 3-MCPD- and glycidyl esters can be mitigated in vegetable oils by use of short path distillation. Eur J Lipid Sci Technol. 118(3):396–405. doi:https://doi.org/10.1002/ejlt.201500095.
- Spungen JH, MacMahon S, Leigh J, Flannery B, Kim G, Chirtel S, Smegal D. 2018. Estimated US infant exposures to 3-MCPD esters and glycidyl esters from consumption of infant formula. Food Addit Contam A. 35(6):1085–1092. doi:https://doi.org/10.1080/19440049.2018.1459051.
- 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(15):3659–3669. doi:https://doi.org/10.1016/j.tet.2005.02.034.
- Steenbergen H, Hrnčiřík K, Ermacora A, de Koning S, Janssen H-G. 2013. Direct analysis of intact glycidyl fatty acid esters in edible oils using gas chromatography–mass spectrometry. J Chromatogr A. 1313:202–211. doi:https://doi.org/10.1016/j.chroma.2013.06.056.
- Wöhrlin F, Fry H, Lahrssen-Wiederholt M, Preiß-Weigert A. 2015. Occurrence of fatty acid esters of 3-MCPD, 2-MCPD and glycidol in infant formula. Food Addit Contam A. 32(11):1810–1822. doi:https://doi.org/10.1080/19440049.2015.1071497.
- 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(1):52–68. doi:https://doi.org/10.1080/19440049.2012.713031.
- 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(4):1800395. doi:https://doi.org/10.1002/ejlt.201800395.