Skip to main content

Advertisement

SpringerLink
Log in

3-MCPD in food other than soy sauce or hydrolysed vegetable protein (HVP)

  • Review
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

This review gives an overview of current knowledge about 3-monochloropropane-1,2-diol (3-MCPD) formation and detection. Although 3-MCPD is often mentioned with regard to soy sauce and acid-hydrolysed vegetable protein (HVP), and much research has been done in that area, the emphasis here is placed on other foods. This contaminant can be found in a great variety of foodstuffs and is difficult to avoid in our daily nutrition. Despite its low concentration in most foods, its carcinogenic properties are of general concern. Its formation is a multivariate problem influenced by factors such as heat, moisture and sugar/lipid content, depending on the type of food and respective processing employed. Understanding the formation of this contaminant in food is fundamental to not only preventing or reducing it, but also developing efficient analytical methods of detecting it. Considering the differences between 3-MCPD-containing foods, and the need to test for the contaminant at different levels of food processing, one would expect a variety of analytical approaches. In this review, an attempt is made to provide an up-to-date list of available analytical methods and to highlight the differences among these techniques. Finally, the emergence of 3-MCPD esters and analytical techniques for them are also discussed here, although they are not the main focus of this review.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  1. Velisek J, Davidek J, Hajslova J, Kubelka V, Janicek G, Mankova B (1978) Chlorohydrins in protein hydrolysates. Z Lebensm Unters Forsch 167(4):241–244

    Article  CAS  Google Scholar 

  2. Davidek J, Velisek J, Kubelka V, Janicek G, Simicova Z (1980) Glycerol chlorohydrins and their esters as products of the hydrolysis of tripalmitin, tristearin and triolein with hydrochloric acid. Z Lebensm Unters Forsch 171(1):14–17

    Article  CAS  Google Scholar 

  3. Hamlet C, Sadd PA (2009) In: Stadler RH,Lineback DR (ed) Process induced food toxicants: occurrence, formation, mitigation, and health risks. Wiley, Hoboken, NJ

  4. Velisek J (2009) In: Stadler RH,Lineback DR (ed) Process induced food toxicants: occurrence, formation, mitigation, and health risks. Wiley, Hoboken, NJ

  5. Kuballa T, Ruge W (2004) Analysis and detection of 3-monochloropropane-1,2-diol (3-MCPD) in food by GC/MS/MS. Varian GC/MS Appl Note 73(1):1–2

  6. EC (2006) Commission Regulation (EC) No. 1881/2006 of 19 December 2006 setting maximum levels for certain contaminants in foodstuffs. Off J Eur Union L364:5–24

  7. FSANZ (2003) Chloropropanols in food—an analysis of the public health risk (technical report series 15:62). Food Standards Australia New Zealand, Canberra

  8. Matthew BM, Anastasio C (2000) Determination of halogenated mono-alcohols and diols in water by gas chromatography with electron-capture detection. J Chromatogr A 866(1):65–77

    Google Scholar 

  9. Crisp M, Padley I (2007) European wet-strength resin drivers. Tissue World Apr/May

  10. Boden L, Lundgren M, Stensio KE, Gorzynski M (1997) Determination of 1, 3-dichloro-2-propanol and 3-chloro-1, 2-propanediol in papers treated with polyamido amine-epichlorohydrin wet-strength resins by gas chromatography-mass spectrometry using selective ion monitoring. J Chromatogr A 788(1–2):195–203

    Google Scholar 

  11. Schlatter J, Baars AJ, DiNovi M, Lawrie S, Lorentzen R (2002) Safety evaluation of certain food additives and contaminants: 3-chloro-1, 2-propanediol. WHO Food Addit Ser 48:1–30

    Google Scholar 

  12. Pesselman RL, Feit MJ (1988) Determination of residual epichlorohydrin and 3-chloropropanediol in water by gas chromatography with electron-capture detection. J Chromatogr A 439(2):448–452

    Google Scholar 

  13. EC (2004) Collection and collation of data on levels of 3-monochloropropanediol (3-MCPD) and related substances in food (scientific co-operation report). EC Directorate-General of Health and Consumer Protection, Brussels

  14. Cheng WC, Chen HC, Lin YP, Lee HF, Chang PC, Chou SS (2004) Survey on 3-monochloro-1, 2-propandiol (3-MCPD) contents of soy sauce products during fiscal year 2002 in Taiwan. J Food Drug Anal 12(4):336–341

    CAS  Google Scholar 

  15. Crews C, Hasnip S, Chapman S, Hough P, Potter N, Todd J, Brereton P, Matthews W (2003) Survey of chloropropanols in soy sauces and related products purchased in the UK in 2000 and 2002. Food Addit Contam 20(10):916–922

    Article  CAS  Google Scholar 

  16. FSA (2001) Survey of 3-monochloropropane-1,2-diol (3-MCPD) in soy sauce and related products. Food Standards Agency, London

  17. Macarthur R, Crews C, Davies A, Brereton P, Hough P, Harvey D (2000) 3-Monochloropropane-1,2-diol (3-MCPD) in soy sauces and similar products available from retail outlets in the UK. Food Addit Contam 17(11):903–906

    Google Scholar 

  18. Fu WS, Zhao Y, Zhang G, Zhang L, Li JG, Tang CD, Miao H, Bo J, Zhang Q, Wu YN (2007) Occurrence of chloropropanols in soy sauce and other foods in China between 2002 and 2004. Food Addit Contam 24(8):812–819

    Article  CAS  Google Scholar 

  19. Nyman PJ, Diachenko GW, Perfetti GA (2003) Survey of chloropropanols in soy sauces and related products. Food Addit Contam 20(10):909–915

    Article  CAS  Google Scholar 

  20. Wong KO, Cheong YH, Seah HL (2006) 3-Monochloropropane-1,2-diol (3-MCPD) in soy and oyster sauces: occurrence and dietary intake assessment. Food Contr 17(5):408–413

    Google Scholar 

  21. Chung SWC, Kwong KP, Yau JCW, Wong AMC, Xiao Y (2008) Chloropropanols levels in foodstuffs marketed in Hong Kong. J Food Compos Anal 21(7):569–573

    Article  CAS  Google Scholar 

  22. Crews C, Brereton P, Davies A (2001) The effects of domestic cooking on the levels of 3-monochloropropanediol in foods. Food Addit Contam 18(4):271–280

    CAS  Google Scholar 

  23. Crews C, Hough P, Brereton P, Harvey D, Macarthur R, Matthews W (2002) Survey of 3-monochloropropane-1,2-diol (3-MCPD) in selected food groups, 1999–2000. Food Addit Contam 19(1):22–27

    Google Scholar 

  24. FSA (2001) Survey of 3-monochloropropane-1,2-diol (3-MCPD) in selected food groups. Food Standards Agency, London

  25. Divinova V, Svejkovska B, Novotny O, Velisek J (2004) Survey of 3-chloropropane-1,2-diol and its precursors in foods in the Czech Republic. Czech J Food Sci 22:267–271

    Google Scholar 

  26. Massey R (2007) Fight against 3-MCPD. Food Manufact 82:35–36

    Google Scholar 

  27. FAO/WHO (2006) Discussion paper on acid HVP containing products and other products containing chloropropanols. In: Proc Session 38 of Codex Committee on Food Additives and Contaminants, The Hague, The Netherlands, 24–28 Apr 2006

  28. Cho WS, 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

    Google Scholar 

  29. Olsen P (1993) Chloropropanols (WHO Food Additives Series 32). http://www.inchem.org/documents/jecfa/jecmono/v32je17.htm. Accessed 05 Nov 2008

  30. SCF (2001) Opinion of the Scientific Committee on Food on 3-monochloro-propane-1,2-diol (3-MCPD): updating the SCF opinion of 1994 (SCF/CS/CNTM/OTH/17, final version). EC, Brussels

  31. Lynch BS, Bryant DW, Hook GJ, Nestmann ER, Munro IC (1998) Carcinogenicity of monochloro-1,2-propanediol (α-chlorohydrin, 3-MCPD). Int J Toxicol 17(1):47–76

    Google Scholar 

  32. JECFA (2001) Summary of the fifty-seventh meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA). FAO/WHO, Rome

    Google Scholar 

  33. FAO, WHO (2007) Discussion paper on chloropropanols derived from the manufacture of acid-HVP and the heat processing of food. In: Proc 1st Session of Codex Committee on Contaminants in Foods, Beijing, China, 16–20 April 2007

  34. Collier PD, Cromie DDO, Davies AP (1991) Mechanism of formation of chloropropanols present in protein hydrolysates. J Am Oil Chem Soc 68(10):785–790

    Article  CAS  Google Scholar 

  35. Hamlet CG, Sadd PA, Crews C, Velisek J, Baxter DE (2002) Occurrence of 3-chloro-propane-1, 2-diol (3-MCPD) and related compounds in foods: a review. Food Addit Contam 19(7):619–631

    Google Scholar 

  36. Massey R, Hamlet C (2007) Chloropropanol contaminants in food: the story continues. Food Sci Tech 21(4):32–34

    Google Scholar 

  37. Calta P, Velisek J, Dolezal M, Hasnip S, Crews C, Reblova Z (2004) Formation of 3-chloropropane-1,2-diol in systems simulating processed foods. Eur Food Res Tech 218(6):501–506

    Google Scholar 

  38. Reece P (2005) The origin and formation of 3-MCPD in foods and food ingredients (final project report). Food Standards Agency, London

  39. Dolezal M, Calta P, Velisek J (2004) Formation and decomposition of 3-chloropropane-1,2-diol in model systems. Czech J Food Sci 22:263–266

    Google Scholar 

  40. Hamlet CG, Sadd PA, Gray DA (2004) Generation of monochloropropanediols (MCPDs) in model dough systems. 1. Leavened doughs. J Agr Food Chem 52(7):2059–2066

    Google Scholar 

  41. 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 Tech 216(2):122–128

    CAS  Google Scholar 

  42. Stadler RH, Theurillat V, Studer A, Scanlan F, Seefelder W (2007) In: SKLM SCoFS (ed) Thermal processing of food: potential health benefits and risks (Forschungsberichte (DFG)), 1st edn. Wiley-VCH, Weinheim

  43. Robert MC, Oberson JM, Stadler RH (2004) Model studies on the formation of monochloropropanediols in the presence of lipase. J Agr Food Chem 52(16):5102–5108

    Article  CAS  Google Scholar 

  44. Breitling-Utzmann CM (2002) 3-MCPD: Untersuchungen in Lebensmitteln. Bundesverband der Lebensmittelchemiker/-innen im öffentlichen Dienst e.V. (BLC). http://www.lebensmittel.org/lebensm/mcpd.htm. Accessed Nov 2008

  45. Breitling-Utzmann CM, Kobler H, Harbolzheimer D, Maier A (2003) 3-MCPD: occurrence in bread crust and various food groups as well as formation in toast. Dtsch Lebensm Rundsch 99(7):280–285

    Google Scholar 

  46. Breitling-Utzmann CM, Hrenn H, Haase NU, Unbehend GM (2005) Influence of dough ingredients on 3-chloropropane-1,2-diol (3-MCPD) formation in toast. Food Addit Contam 22(2):97–103

    Google Scholar 

  47. Hamlet CG, Sadd PA (2004) Effects of yeast stress and organic acids on chloropropanols formation in cereal products. Czech J Food Sci 22:255–258

    Google Scholar 

  48. Hamlet CG, Sadd PA, Gray DA (2004) Generation of monochloropropanediols (MCPDs) in model dough systems. 2. Unleavened doughs. J Agr Food Chem 52(7):2067–2072

    Google Scholar 

  49. 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(1):15–21

    Google Scholar 

  50. Divinova V, Dolezal M, Velisek J (2007) Free and bound 3-chloropropane-1,2-diol in coffee surrogates and malts. Czech J Food Sci 25(1):39–47

    Google Scholar 

  51. Dolezal M, Chaloupska M, Divinova V, Svejkovska B, Velisek J (2005) Occurrence of 3-chloropropane-1,2-diol and its esters in coffee. Eur Food Res Tech 221(3–4):221–225

    Google Scholar 

  52. Kuntzer J, Weißhaar R (2006) The smoking process: a potent source of 3-chloropropane-1,2-diol (3-MCPD) in meat products. Dtsch Lebensm Rundsch 102(9):397–400

    Google Scholar 

  53. Retho C, Blanchard F (2005) Determination of 3-chloropropane-1,2-diol as its 1,3-dioxolane derivative at the μg kg−1 level: application to a wide range of foods. Food Addit Contam 22(12):1189–1197

    Google Scholar 

  54. Wenzl T, Lachenmeier DW, Gokmen V (2007) Analysis of heat-induced contaminants (acrylamide, chloropropanols and furan) in carbohydrate-rich food. Anal Bioanal Chem 389(1):119–137

    Article  CAS  Google Scholar 

  55. Van Rillaer W, Beernaert H (1989) Determination of residual 1, 3-dichloro-2-propanol in protein hydrolysates by capillary gas chromatography. Z Lebensm Untersuch Forsch 188(4):343–345

    Article  Google Scholar 

  56. EC (2007) Commission Regulation (EC) No 333/2007 of 28 March 2007 laying down the methods of sampling and analysis for the official control of the levels of lead, cadmium, mercury, inorganic tin, 3-MCPD and benzo(a)pyrene in foodstuffs. Off J Eur Union L88:29–38

    Google Scholar 

  57. CEN (2004) Foodstuffs: determination of 3-monochloropropane-1,2-diol by GC/MS (EN 14573). European Committee for Standardization, Brussels

  58. Brereton P, Kelly J, Crews C, Honour S, Wood R, Davies A (2001) Determination of 3-chloro-1,2-propanediol in foods and food ingredients by gas chromatography with mass spectrometric detection: collaborative study. JAOAC Int 84(2):455–465

    Google Scholar 

  59. Hamlet CG (1998) Analytical methods for the determination of 3-chloro-1,2-propandiol and 2-chloro-1,3-propandiol in hydrolysed vegetable protein, seasonings and food products using gas chromatography/ion trap tandem mass spectrometry. Food Addit Contam 15(4):451–465

    Google Scholar 

  60. Van Bergen CA, Collier PD, Cromie DDO, Lucas RA, Preston HD, Sissons DJ (1992) Determination of chloropropanols in protein hydrolysates. J Chromatogr 589(1–2):109–119

    Google Scholar 

  61. Xu X, Ren Y, Wu P, Han J, Shen X (2006) The simultaneous separation and determination of chloropropanols in soy sauce and other flavoring with gas chromatography-mass spectrometry in negative chemical and electron impact ionization modes. Food Addit Contam 23(2):110–119

    Article  CAS  Google Scholar 

  62. Chung WC, Hui KY, Cheng SC (2002) Sensitive method for the determination of 1,3-dichloropropan-2-ol and 3-chloropropane-1,2-diol in soy sauce by capillary gas chromatography with mass spectrometric detection. J Chromatogr A 952(1–2):185–192

    Google Scholar 

  63. Abu-El-Haj S, Bogusz MJ, Ibrahim Z, Hassan H, Al Tufail M (2007) Rapid and simple determination of chloropropanols (3-MCPD and 1,3-DCP) in food products using isotope dilution GC-MS. Food Contr 18(1):81–90

    Google Scholar 

  64. Nyman PJ, Diachenko GW, Perfetti GA (2003) Determination of 1,3-dichloropropanol in soy and related sauces by using gas chromatography/mass spectrometry. Food Addit Contam 20(10):903–908

  65. Meierhans DC, Bruehlmann S, Meili J, Taeschler C (1998) Sensitive method for the determination of 3-chloropropane-1,2-diol and 2-chloropropane-1,3-diol by capillary gas chromatography with mass spectrometric detection. J Chromatogr A 802(2):325–333

    Google Scholar 

  66. Leon N, Yusa V, Pardo O, Pastor A (2008) Determination of 3-MCPD by GC-MS/MS with PTV-LV injector used for a survey of Spanish foodstuffs. Talanta 75(3):824–831

    Article  CAS  Google Scholar 

  67. Rodman LE, Ross RD (1986) Gas-liquid chromatography of 3-chloropropanediol. J Chromatogr A 369(C):97–103

    Google Scholar 

  68. Plantinga WJ, Van Toorn WG, Van der Stegen GHD (1991) Determination of 3-chloropropane-1,2-diol in liquid hydrolysed vegetable proteins by capillary gas chromatography with flame ionization detection. J Chromatogr 555(1–2):311–314

    Google Scholar 

  69. Bundesinstitut für Gesundheitlichen Verbraucherschutz und Veterinärmedizin (1995) Bestimmung von 3-Chlor-1,2-Propandiol (3-MDCP) in Speisewürzen (Eiweisshydrolysate) (No 52.02 1). Beuth Verlag, Berlin

  70. Divinova V, Svejkovska B, Dolezal M, Velisek J (2004) Determination of free and bound 3-chloropropane-1,2-diol by gas chromatography with mass spectrometric detection using deuterated 3-chloropropane-1,2-diol as internal standard. Czech J Food Sci 22(5):182–189

    Google Scholar 

  71. Dayrit FM, Ninonuevo MR (2004) Development of an analytical method for 3-monochloropropane-1,2-diol in soy sauce using 4-heptanone as derivatizing agent. Food Addit Contam 21(3):204–209

    Google Scholar 

  72. Xing X, Cao Y, Wang L (2005) Determination of rate constants and activation energy of 3-chloro-1,2-propanediol hydrolysis by capillary electrophoresis with electrochemical detection. J Chromatogr A 1072(2):267–272

    Google Scholar 

  73. Xing X, Cao Y (2007) Determination of 3-chloro-1,2-propanediol in soy sauces by capillary electrophoresis with electrochemical detection. Food Contr 18(2):167–172

    Google Scholar 

  74. Hamlet CG, Sadd PA (2002) Kinetics of 3-chloropropane-1,2-diol (3-MCPD) degradation in high temperature model systems. Eur Food Res Tech 215(1):46–50

    Google Scholar 

  75. Wittmann R (1991) Bestimmung von Dichlorpropanolen und Monochlorpropandiolen in Wurzen und wurzehaltigen Lebensmitteln (Determination of dichloropropanols and monochloropropandiols in seasonings and in foodstuffs containing seasonings). Z Lebensm Unters Forsch 193(3):224–229

    Article  CAS  Google Scholar 

  76. Crews C, LeBrun G, Brereton PA (2002) Determination of 1,3-dichloropropanol in soy sauces by automated headspace gas chromatography-mass spectrometry. Food Addit Contam 19(4):343–349

    Google Scholar 

  77. Hasnip S, Crews C, Potter N, Brereton P, Diserens H, Oberson JM, Baigrie B, Byrd N, Campbell DJ, Diserens H, Hageman L, Hollywood F, Noro Y, Nyman P, Wehage H (2005) Determination of 1,3-dichloropropanol in soy sauce and related products by headspace gas chromatography with mass spectrometric detection: interlaboratory study. J AOAC Int 88(5):1404–1412

    Google Scholar 

  78. Huang M, Jiang G, He B, Liu J, Zhou Q, Fu W, Wu Y (2005) Determination of 3-chloropropane-1,2-diol in liquid hydrolyzed vegetable proteins and soy sauce by solid-phase microextraction and gas chromatography/mass spectrometry. Anal Sci 21(11):1343–1347

    Google Scholar 

  79. Lee MR, Chiu TC, Dou J (2007) Determination of 1,3-dichloro-2-propanol and 3-chloro-1,2-propandiol in soy sauce by headspace derivatization solid-phase microextraction combined with gas chromatography-mass spectrometry. Anal Chim Acta 591(2):167–172

    Google Scholar 

  80. Hamlet CG, Sutton PG (1997) Determination of the chloropropanols, 3-chloro-1,2-propandiol and 2-chloro-1,3-propandiol, in hydrolysed vegetable proteins and seasonings by gas chromatography/ion trap tandem mass spectrometry. Rapid Comm Mass Spectrom 11(13):1417–1424

    Google Scholar 

  81. Kuballa T, Ruge W (2003) Nachweis und Bestimmung von 3-Monochlorpropan-1,2-diol (3-MCPD) mit GC-MS/MS. Lebensmittelchem 57(3):57–58

    Google Scholar 

  82. Kissa E (1992) Determination of 3-chloropropanediol and related dioxolanes by gas chromatography. J Chromatogr 605(1):134–138

    Google Scholar 

  83. Spyres G (1993) Determination of 3-chloropropane-1,2-diol in hydrolyzed vegetable proteins by capillary gas chromatography with electrolytic conductivity detection. J Chromatogr 638(1):71–74

    Google Scholar 

  84. ILSI (2009) Workshop on 3-MCPD Esters in Food Products. http://europe.ilsi.org/events/past/Workshop3MCPDesters.htm. Accessed May 2009

  85. Weißhaar R (2009) Fatty acid esters of 3-MCPD: overview of occurrence in different types of foodstuffs. In: Proc Workshop on 3-MCPD Esters in Food Products, Brussels, Belgium, 5–6 Feb 2009

  86. Hamlet CG, Sadd PA (2004) Chloropropanols and their esters in cereal products. Czech J Food Sci 22:259–262

    Google Scholar 

  87. 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(2):183–186

    Google Scholar 

  88. Sim CW, Muhammad K, Yusof S, Bakar J, Hashim DM (2004) The optimization of conditions for the production of acidhydrolysed winged bean and soybean proteins with reduction of 3-monochloropropane-1,2-diol (3-MCPD). Int J Food Sci Tech 39(9):947–958

    Google Scholar 

  89. Velisek J, Calta P, Crews C, Hasnip S, Dolezal M (2003) 3-Chloropropane-1,2-diol in models simulating processed foods: precursors and agents causing its decomposition. Czech J Food Sci 21(5):153–161

    Google Scholar 

Download references

Acknowledgements

The referees of this review are kindly acknowledged for their constructive advice and helpful comments.

Author information

Authors and Affiliations

  1. EC-JRC-Institute for Reference Materials and Measurements (IRMM), Retieseweg 111, 2440, Geel, Belgium

    Ines Baer, Beatriz de la Calle & Philip Taylor

Authors
  1. Ines Baer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Beatriz de la Calle
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Philip Taylor
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Beatriz de la Calle.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Baer, I., de la Calle, B. & Taylor, P. 3-MCPD in food other than soy sauce or hydrolysed vegetable protein (HVP). Anal Bioanal Chem 396, 443–456 (2010). https://doi.org/10.1007/s00216-009-3177-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-009-3177-y

Keywords

Search

Navigation