1932

Abstract

Fatty acid esters of 3-monochloropropane-1,2-diol (3-MCPD esters) are a new group of processing-induced chemical toxicants with possible nephrotoxicity and testicular toxicity. 3-MCPD esters have been detected in many food categories, including refined edible oils, bread, coffee, and infant formula. 3-MCPD esters have also been detected in human breast milk, indicating their possible absorption and distribution in human organs and tissues. 3-MCPD esters have become a food safety concern, and in 2013 the European Food Safety Authority estimated a tolerable daily value (TDI) of 2 μg/kg body weight (BW) for the amount of free 3-MCPD. This review summarizes the available information on 3-MCPD ester research, including the analytical methods, exposure biomarkers, absorption and metabolism, toxicities, formation mechanisms, and mitigation strategies as well as the occurrence of 3-MCPD esters in human foods. This review may serve as a scientific foundation for advancing our understanding of 3-MCPD esters and their food safety concerns.

Loading

Article metrics loading...

/content/journals/10.1146/annurev-food-032818-121245
2019-03-25
2024-04-19
Loading full text...

Full text loading...

/deliver/fulltext/food/10/1/annurev-food-032818-121245.html?itemId=/content/journals/10.1146/annurev-food-032818-121245&mimeType=html&fmt=ahah

Literature Cited

  1. Abraham K, Appel KE, Berger-Preiss E, Apel E, Gerling S et al. 2013. Relative oral bioavailability of 3-MCPD from 3-MCPD fatty acid esters in rats. Arch. Toxicol. 87:649–59
    [Google Scholar]
  2. Andreoli R, Cirlini M, Mutti A 2015. Quantification of 3-MCPD and its mercapturic metabolite in human urine: validation of an LC-MS-MS method and its application in the general population. Anal. Bioanal. Chem. 407:4823–27
    [Google Scholar]
  3. AOCS (Am. Oil Chem. Soc.). 2017. 2- and 3-MCPD fatty acid esters and glycidol fatty acid esters in edible oils and fats by alkaline transesterification and GC/MS. AOCS Off. Method Cd:29b–13
    [Google Scholar]
  4. Arisseto AP, Marcolino PFC, Vicente E 2015. 3-Monochloropropane-1,2-diol fatty acid esters in commercial deep-fat fried foods. Food Addit. Contam. Part A 32:1431–35
    [Google Scholar]
  5. Arisseto AP, Silva WC, Scaranelo GR, Vicente E 2017. 3-MCPD and glycidyl esters in infant formulas from the Brazilian market: occurrence and risk assessment. Food Control 77:76–81
    [Google Scholar]
  6. Baer I, Calle BDE, Taylor P 2010. 3-MCPD in food other than soy sauce or hydrolysed vegetable protein (HVP). Anal. Bioanal. Chem. 396:443–56
    [Google Scholar]
  7. Barocelli E, Corradi A, Mutti A, Petronini PG 2011. Comparison between 3-MCPD and its palmitic esters in a 90-day toxicological study. EFSA Support. Publ. 8:1–131
    [Google Scholar]
  8. 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 Compos. Anal. 44:111–14
    [Google Scholar]
  9. Bornscheuer UT, Hesseler M 2010. Enzymatic removal of 3-monochloro-1,2-propanediol (3-MCPD) and its esters from oils. Eur. J. Lipid Sci. Technol. 112:552–56
    [Google Scholar]
  10. Braeuning A, Sawada S, Oberemm A, Lampen A 2015. Analysis of 3-MCPD- and 3-MCPD dipalmitate-induced proteomic changes in rat liver. Food Chem. Toxicol. 86:374–84
    [Google Scholar]
  11. Cheng W, Liu G, Wang L, Liu Z 2017. Glycidyl fatty acid esters in refined edible oils: a review on formation, occurrence, analysis, and elimination methods. Compr. Rev. Food Sci. Food Saf. 16:263–81
    [Google Scholar]
  12. Christie WW, Sébédio JL, Juanéda P 2017. Analysis of conjugated linoleic acid (CLA). AOCS Lipid Libr http://lipidlibrary.aocs.org/Analysis/content.cfm?ItemNumber=40371
  13. Chung HY, Chung SWC, Chan BTP, Ho YY, Xiao Y 2013.a Dietary exposure of Hong Kong adults to fatty acid esters of 3-monochloropropane-1,2-diol. Food Addit. Contam. Part A 30:1508–12
    [Google Scholar]
  14. Chung SWC, Chan BTP, Chung HY, Xiao Y, Ho YY 2013.b Occurrence of bound 3-monochloropropan-1,2-diol content in commonly consumed foods in Hong Kong analysed by enzymatic hydrolysis and GC-MS detection. Food Addit. Contam. Part A 30:1248–54
    [Google Scholar]
  15. Collier PD, Cromie DDO, Davies AP 1991. Mechanism of formation of chloropropanols present in protein hydrolysates. J. Am. Oil Chem. Soc. 68:785–90
    [Google Scholar]
  16. Craft BD, Nagy K 2012. Mitigation of MCPD-ester and glycidyl-ester levels during the production of refined palm oil. Lipid Technol 24:155–57
    [Google Scholar]
  17. 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. Part A-Chem. 29:29–37
    [Google Scholar]
  18. 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
    [Google Scholar]
  19. 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
    [Google Scholar]
  20. Eur. Food Saf. Auth. (EFSA). 2013. Analysis of occurrence of 3-monochloropropane-1,2-diol (3-MCPD) in food in Europe in the years 2009–2011 and preliminary exposure assessment. EFSA J 11:93381
    [Google Scholar]
  21. Eur. Food Saf. Auth. (EFSA). 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 14:54426
    [Google Scholar]
  22. Fu WS, Zhao YF, Zhang G, Zhang L, Li JG et al. 2007. Occurrence of chloropropanols in soy sauce and other foods in China between 2002 and 2004. Food Addit. Contam. Part A 24:812–19
    [Google Scholar]
  23. Gao B, Liu M, Huang G, Zhang Z, Zhao Y et al. 2017. Absorption, distribution, metabolism and excretion of 3-MCPD 1-monopalmitate after oral administration in rats. J. Agric. Food Chem. 65:2609–14
    [Google Scholar]
  24. Gardner AM, Yurawecz MP, Cunningham WC, Diachenko GW, Mazzola EP, Brumley WC 1983. Isolation and identification of C16 and C18 fatty acid esters of chloropropanediol in adulterated Spanish cooking oils. Bull. Environ. Contam. Toxicol. 31:625–30
    [Google Scholar]
  25. Ger. Soc. Fat Sci. (DGF). 2012. Ergänzende Hinweise zu den DGF‐Einheitsmethoden C‐VI 17 (10) und C‐VI 18 (10) zur Bestimmung der 3‐MCPD‐ und Glycidyl‐Ester Frankfurt, Ger: DGF
  26. 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
    [Google Scholar]
  27. Hamlet CG, Jayaratne SM, Matthews W 2002. 3-Monochloropropane-1,2-diol (3-MCPD) in food ingredients from UK food producers and ingredient suppliers. Food Addit. Contam. 19:15–21
    [Google Scholar]
  28. Hamlet CG, Sadd PA 2004. Chloropropanols and their esters in cereal products. Czech. J. Food Sci. 22:259–62
    [Google Scholar]
  29. Hamlet CG, Sadd PA, Gray DA 2003. Influence of composition, moisture, pH and temperature on the formation and decay kinetics of monochloropropanediols in wheat flour dough. Eur. Food Res. Technol. 216:122–28
    [Google Scholar]
  30. Hamlet CG, Sadd PA, Gray DA 2004. Generation of monochloropropanediols (MCPDs) in model dough systems. 2. Unleavened doughs. J. Agric. Food Chem. 52:2067–72
    [Google Scholar]
  31. 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. LWT Food Sci. Technol. 48:204–8
    [Google Scholar]
  32. Huang G, Xue J, Sun X, Wang J, Yu L 2018.a Necroptosis in 3-MCPD-dipalmitate-induced acute kidney injury in vivo and its repression by miR-223–3p. Toxicology 406–7:33–43
    [Google Scholar]
  33. Huang G, Xue J, Sun X, Wang J, Wang Y et al. 2018.b Suppression of T lymphocyte activation by 3-chloro-1,2-propanediol mono- and di-palmitate esters in vitro. Toxicol. In Vitro 51:54–62
    [Google Scholar]
  34. Ji J, Zhang L, Zhang H, Sun C, Sun J et al. 2016. 1 H NMR-based urine metabolomics for the evaluation of kidney injury in Wistar rats by 3-MCPD. Toxicol. Res. 5:689–96
    [Google Scholar]
  35. Joint FAO/WHO Exp. Comm. Food Addit. (JECFA). 2016. Summary Report of the Eighty-Third Meeting of JECFA Geneva, Switz: WHO http://www.fao.org/3/a-bq821e.pdf
  36. Jumaah F, Jędrkiewicz R, Gromadzka J, Namiesnik J, Essen S et al. 2017. Rapid and green separation of mono- and diesters of monochloropropanediols by ultrahigh performance supercritical fluid chromatography-mass spectrometry using neat carbon dioxide as a mobile phase. J. Agric. Food Chem. 65:8220–28
    [Google Scholar]
  37. Karl H, Merkle S, Kuhlmann J, Fritsche J 2016. Development of analytical methods for the determination of free and ester bound 2-, 3-MCPD, and esterified glycidol in fishery products. Eur. J. Lipid Sci. Technol. 118:406–17
    [Google Scholar]
  38. Koyama K, Miyazaki K, Abe K, Egawa Y, Kido H et al. 2016. Collaborative study of an indirect enzymatic method for the simultaneous analysis of 3-MCPD, 2-MCPD, and glycidyl esters in edible oils. J. Oleo Sci. 65:557–68
    [Google Scholar]
  39. Kusters M, Bimber U, Ossenbruggen A, Reeser S, Gallitzendorfer R, Gerhartz M 2010. Rapid and simple micromethod for the simultaneous determination of 3-MCPD and 3-MCPD esters in different foodstuffs. J. Agric. Food Chem. 58:6570–77
    [Google Scholar]
  40. Kusters M, Bimber U, Reeser S, Gallitzendorfer R, Gerhartz M 2011. Simultaneous determination and differentiation of glycidyl esters and 3-monochloropropane-1,2-diol (MCPD) esters in different foodstuffs by GC-MS. J. Agric. Food Chem. 59:6263–70
    [Google Scholar]
  41. Leigh J, MacMahon S 2017. Occurrence of 3-monochloropropanediol esters and glycidyl esters in commercial infant formulas in the United States. Food Addit. Contam. Part A 34:356–70
    [Google Scholar]
  42. Li C, Li L, Jia H, Wang Y, Shen M et al. 2016. Formation and reduction of 3-monochloropropane-1,2-diol esters in peanut oil during physical refining. Food Chem 199:605–11
    [Google Scholar]
  43. Li H, Chen D, Miao H, Zhao Y, Shen J et al. 2015. Direct determination of fatty acid esters of 3-chloro-1,2-propanediol in edible vegetable oils by isotope dilution-ultra high performance liquid chromatography-triple quadrupole mass spectrometry. J. Chromatogr. 1410:99–109
    [Google Scholar]
  44. Li J, Wang S, Wang M, Shi W, Du X et al. 2013. The toxicity of 3-chloropropane-1,2-dipalmitate in Wistar rats and a metabonomics analysis of rat urine by ultra-performance liquid chromatography-mass spectrometry. Chem. Biol. Interact. 206:337–45
    [Google Scholar]
  45. Liu M, Gao B, Qin F, Wu P, Shi H et al. 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. 50:3785–91
    [Google Scholar]
  46. Liu M, Huang G, Wang TTY, Sun X, Yu L 2016. 3-MCPD 1-palmitate induced tubular cell apoptosis in vivo via JNK/p53 pathways. Toxicol. Sci. 151:181–92
    [Google Scholar]
  47. Liu M, Liu J, Wu Y, Gao B, Wu P et al. 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. 97:841–48
    [Google Scholar]
  48. Liu Q, Han F, Xie K, Miao H, Wu Y 2013. Simultaneous determination of total fatty acid esters of chloropropanols in edible oils by gas chromatography-mass spectrometry with solid-supported liquid-liquid extraction. J. Chromatogr. 1314:208–15
    [Google Scholar]
  49. Lu J, Wang Z, Ren M, Feng G, Ye B et al. 2015. A 4-week study of four 3-monochloropropane-1,2-diol diesters on lipid metabolism in C57BL/6J mice. Environ. Toxicol. Pharmacol. 40:453–58
    [Google Scholar]
  50. MacMahon S, Begley TH, Diachenko GW 2013.b Occurrence of 3-MCPD and glycidyl esters in edible oils in the United States. Food Addit. Contam. Part A 30:2081–92
    [Google Scholar]
  51. MacMahon S, Mazzola E, Begley TH, Diachenko GW 2013.a Analysis of processing contaminants in edible oils. Part 1. Liquid thromatography–tandem mass spectrometry method for the direct detection of 3-monochloropropanediol monoesters and glycidyl esters. J. Agric. Food Chem. 61:4737–47
    [Google Scholar]
  52. 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. 62:11647–56
    [Google Scholar]
  53. Matthäus B, Pudel F 2013. Mitigation of 3‐MCPD and glycidyl esters within the production chain of vegetable oils especially palm oil. Lipid Technol 25:151–55
    [Google Scholar]
  54. Matthäus B, Pudel F 2014. Mitigation of MCPD and glycidyl esters in edible oils. Processing Contaminants in Edible Oils: MCPD and Glycidal Esters S MacMahon 23–55 Urbana, IL: AOCS Press
    [Google Scholar]
  55. 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. 113:380–86
    [Google Scholar]
  56. Merkle S, Ostermeyer U, Rohn S, Karl H, Fritsche J 2018. Mitigation strategies for ester bound 2-/3-MCPD and esterified glycidol in pre-fried breaded and frozen fish products. Food Chem 245:196–204
    [Google Scholar]
  57. Onami S, Cho YM, Toyoda T, Horibata K, Ishii Y et al. 2014.a Absence of in vivo genotoxicity of 3-monochloropropane-1,2-diol and associated fatty acid esters in a 4-week comprehensive toxicity study using F344 gpt delta rats. Mutagenesis 29:295–302
    [Google Scholar]
  58. Onami S, Cho YM, Toyoda T, Mizuta Y, Yoshida M et al. 2014.b A 13-week repeated dose study of three 3-monochloropropane-1,2-diol fatty acid esters in F344 rats. Arch. Toxicol. 88:871–80
    [Google Scholar]
  59. Pudel F, Benecke P, Fehling P, Freudenstein A, Matthäus B et al. 2011. On the necessity of edible oil refining and possible sources of 3‐MCPD and glycidyl esters. Eur. J. Lipid Sci. Technol. 113:368–73
    [Google Scholar]
  60. Rahn AKK, Yaylayan VA 2011.a Monitoring cyclic acyloxonium ion formation in palmitin systems using infrared spectroscopy and isotope labelling technique. Eur. J. Lipid Sci. Technol. 113:330–34
    [Google Scholar]
  61. Rahn AKK, Yaylayan VA 2011.b What do we know about the molecular mechanism of 3-MCPD ester formation?. Eur. J. Lipid Sci. Technol. 113:323–29
    [Google Scholar]
  62. Ramli MR, Siew WL, Ibrahim NA, Kuntom A, Abd Razak RA 2015. Other factors to consider in the formation of chloropropandiol fatty esters in oil processes. Food Addit. Contam. 32:817–24
    [Google Scholar]
  63. Samaras VG, Giri A, Zelinková Z, Karasek L, Buttinger G 2016. Analytical method for the trace determination of esterified 3- and 2-monochloropropanediol and glycidyl fatty acid esters in various food matrices. J. Chromatogr. A 1466:136–47
    [Google Scholar]
  64. Sawada S, Oberemm A, Buhrke T, Meckert C, Rozycki C et al. 2015. Proteomic analysis of 3-MCPD and 3-MCPD dipalmitate toxicity in rat testis. Food Chem. Toxicol. 83:84–92
    [Google Scholar]
  65. Sawada S, Oberemm A, Buhrke T, Merschenz J, Braeuning A et al. 2016. Proteomic analysis of 3-MCPD and 3-MCPD dipalmitate-induced toxicity in rat kidney. Arch. Toxicol. 90:1437–48
    [Google Scholar]
  66. Schilter B, Scholz G, Seefelder W 2011. Fatty acid esters of chloropropanols and related compounds in food: toxicological aspects. Eur. J. Lipid Sci. Technol. 113:309–13
    [Google Scholar]
  67. Seefelder W, Varga N, Studer A, Williamson G, Scanlan FP et al. 2008. Esters of 3-chloro-1,2-propanediol (3-MCPD) in vegetable oils: significance in the formation of 3-MCPD. Food Addit. Contam. 25:391–400
    [Google Scholar]
  68. Šmidrkal J, Ilko V, Filip V, Doležal M, Zelinková Z et al. 2011. Formation of acylglycerol chloro derivatives in vegetable oils and mitigation strategy. Czech. J. Food Sci. 29:448–56
    [Google Scholar]
  69. Šmidrkal J, Tesařová M, Hrádková I, Berčíková M, Adamčíková A et al. 2016. Mechanism of formation of 3-chloropropan-1,2-diol (3-MCPD) esters under conditions of the vegetable oil refining. Food Chem 211:124–29
    [Google Scholar]
  70. Starski A, Jedra M, Gawarska H, Postupolski J 2013. Assessing exposure to 3-MCPD from bakery products based on monitoring studies undertaken throughout Poland. Rocz. Panstw. Zakl. Hig. 64:277–83
    [Google Scholar]
  71. Strijowski U, Heinz V, Franke K 2011. Removal of 3‐MCPD esters and related substances after refining by adsorbent material. Eur. J. Lipid Sci. Technol. 113:387–92
    [Google Scholar]
  72. Svejkovská B, Doležal M, Velíšek J 2006. Formation and decomposition of 3-chloropropane-1,2-diol esters in models simulating processed foods. Czech. J. Food Sci. 24:172–79
    [Google Scholar]
  73. Svejkovská B, Novotný O, Divinová V, Réblová Z, Doležal M et al. 2004. Esters of 3-chloropropane-1,2-diol in foodstuffs. Czech. J. Food Sci. 22:190–96
    [Google Scholar]
  74. Weißhaar R 2008. Determination of total 3-chloropropane-1,2-diol (3-MCPD) in edible oils by cleavage of MCPD esters with sodium methoxide. Eur. J. Lipid Sci. Technol. 110:183–86
    [Google Scholar]
  75. Weißhaar R 2011. Fatty acid esters of 3-MCPD: Overview of occurrence and exposure estimates. Eur. J. Lipid Sci. Technol. 113:304–8
    [Google Scholar]
  76. 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. Part A 32:1810–22
    [Google Scholar]
  77. Wong YH, Muhamad H, Abas F, Lai OM, Nyam KL et al. 2017. Effects of temperature and NaCl on the formation of 3-MCPD esters and glycidyl esters in refined, bleached and deodorized palm olein during deep-fat frying of potato chips. Food Chem 219:126–30
    [Google Scholar]
  78. Zelinková Z, Doležal M, Velíšek J 2009. Occurrence of 3-chloropropane-1,2-diol fatty acid esters in infant and baby foods. Eur. Food Res. Technol. 228:571–78
    [Google Scholar]
  79. Zelinková Z, Novotný O, Schůrek J, Velíšek J, Hajslová J et al. 2008. Occurrence of 3-MCPD fatty acid esters in human breast milk. Food Addit. Contam. Part A 25:669–76
    [Google Scholar]
  80. Zelinková Z, Svejkovská B, Velíšek J, Doležal M 2006. Fatty acid esters of 3-chloropropane-1,2-diol in edible oils. Food Addit. Contam. 23:1290–98
    [Google Scholar]
  81. Zhang H, Jin P, Zhang M, Cheong L, Hu P et al. 2016. Mitigation of 3-monochloro-1,2-propanediol ester formation by radical scavengers. J. Agric. Food Chem. 64:5887–92
    [Google Scholar]
  82. Zhang X, Gao B, Qin F, Shi H, Jiang Y et al. 2013. Free radical mediated formation of 3-monochloropropanediol (3-MCPD) fatty acid diesters. J. Agric. Food Chem. 61:2548–55
    [Google Scholar]
  83. Zhang Z, Gao B, Zhang X, Jiang Y, Xu X et al. 2015. Formation of 3-monochloro-1,2-propanediol (3-MCPD) di- and monoesters from tristearoylglycerol (TSG) and the potential catalytic effect of Fe2+ and Fe3+. J. Agric. Food Chem. 63:1839–48
    [Google Scholar]
  84. Zhao Y, Zhang Y, Zhang Z, Liu J, Wang Y et al. 2016. Formation of 3-MCPD fatty acid esters from monostearoyl glycerol and the thermal stability of 3-MCPD. J. Agric. Food Chem. 64:8918–26
    [Google Scholar]
  85. Zwagerman R, Overman P 2016. A novel method for the automatic sample preparation and analysis of 3-MCPD-, 2-MCPD-, and glycidylesters in edible oils and fats. Eur. J. Lipid Sci. Technol. 118:997–1006
    [Google Scholar]
/content/journals/10.1146/annurev-food-032818-121245
Loading
/content/journals/10.1146/annurev-food-032818-121245
Loading

Data & Media loading...

  • Article Type: Review Article
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error