Skip to main content
Log in

Role of bioactive carbonyl compounds on the conversion of asparagine into acrylamide during heating

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

Role of bioactive carbonyls on the conversion of asparagine into acrylamide during heating under low moisture conditions was investigated using different binary and ternary models. Ascorbic acid, dehydroascorbic acid, curcumin, silymarin, vanillin, and as well as fructose were used to understand their efficiency on acrylamide formation and to identify key intermediates formed in the Maillard reaction during heating at 180 °C. All carbonyls generated significant amounts of acrylamide from asparagine. Their efficiency were in the order of vanillin > fructose > silymarin > ascorbic acid > curcumin > dehydroascorbic acid. High-resolution mass spectrometry analyses of heated reaction mixtures confirmed the presence of Schiff bases of asparagine with given carbonyl and their decarboxylated forms with very high mass accuracy (∆ < 2.0 ppm). There was an inverse relationship between the melting point of carbonyls and the conversion ratio of asparagine. Vanillin having a melting point of 84 °C formed the highest amount of acrylamide. Presence of 1.0 % of vanillin increased acrylamide formation more than 2 times in a crust resembling model system.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Mottram DS, Wedzicha BL, Dodson AT (2002) Acrylamide is formed in the Maillard reaction. Nature 419:448–449

    Article  CAS  Google Scholar 

  2. Stadler RH, Blank I, Varga N, Robert F, Hau J, Guy PA, Robert MC, Riediker S (2002) Acrylamide from Maillard reaction products. Nature 419:449–450

    Article  CAS  Google Scholar 

  3. Yaylayan VA, Wnorowski A, Locas CP (2003) Why asparagine needs carbohydrates to generate acrylamide. J Agric Food Chem 51:1753–1757

    Article  CAS  Google Scholar 

  4. Zyzak DV, Sanders RA, Stojanovic M, Tallmadge DH, Eberhart BL, Ewald DK, Gruber DC, Morsch TR, Strothers MA, Rizzi GP, Villagran MD (2003) Acrylamide formation mechanism in heated foods. J Agric Food Chem 51:4782–4787

    Article  CAS  Google Scholar 

  5. Granvogl M, Jezussek M, Koehler P, Schieberle P (2004) Quantitation of 3-aminopropionamide in potatoes—a minor but potent precursor in acrylamide formation. J Agric Food Chem 52:4751–4757

    Article  CAS  Google Scholar 

  6. Amrein TM, Schonbachler B, Escher F, Amado R (2004) Acrylamide in gingerbread: Critical factors for formation and possible ways for reduction. J Agric Food Chem 52:4282–4288

    Article  CAS  Google Scholar 

  7. Stadler RH, Robert F, Riediker S, Varga N, Davidek T, Devaud S, Goldmann T, Hau J, Blank I (2004) In-depth mechanistic study on the formation of acrylamide and other vinylogous compounds by the Maillard reaction. J Agric Food Chem 52:5550–5558

    Article  CAS  Google Scholar 

  8. Zamora R, Hidalgo FJ (2008) Contribution of lipid oxidation products to acrylamide formation in model systems. J Agric Food Chem 56:6075–6080

    Article  CAS  Google Scholar 

  9. Hidalgo FJ, Delgado RM, Zamora R (2009) Degradation of asparagine to acrylamide by carbonyl-amine reactions initiated by alkadienals. Food Chem 116:779–784

    Article  CAS  Google Scholar 

  10. Gokmen V, Kocadagli T, Goncuoglu N, Mogol BA (2012) Model studies on the role of 5-hydroxymethyl-2-furfural in acrylamide formation from asparagine. Food Chem 132:168–174

    Article  CAS  Google Scholar 

  11. Amrein TM, Bachmann S, Noti A, Biedermann M, Barbosa MF, Biedermann-Brem S, Grob K, Keiser A, Realini P, Escher F, Amado R (2003) Potential of acrylamide formation, sugars, and free asparagine in potatoes: A comparison of cultivars and farming systems. J Agric Food Chem 51:5556–5560

    Article  CAS  Google Scholar 

  12. Becalski A, Lau BPY, Lewis D, Seaman SW (2003) Acrylamide in foods: occurrence, sources, and modeling. J Agric Food Chem 51:802–808

    Article  CAS  Google Scholar 

  13. Biedermann-Brem S, Noti A, Grob K, Imhof D, Bazzocco D, Pfefferle A (2003) How much reducing sugar may potatoes contain to avoid excessive acrylamide formation during roasting and baking? Eur Food Res Technol 217:369–373

    Article  CAS  Google Scholar 

  14. Surdyk N, Rosen J, Andersson R, Aman P (2004) Effects of asparagine, fructose, and baking conditions on acrylamide content in yeast-leavened wheat bread. J Agric Food Chem 52:2047–2051

    Article  CAS  Google Scholar 

  15. Becalski A, Lau BPY, Lewis D, Seaman SW, Hayward S, Sahagian M, Ramesh M, Leclerc Y (2004) Acrylamide in french fries: Influence of free amino acids and sugars. J Agric Food Chem 52:3801–3806

    Article  CAS  Google Scholar 

  16. Elmore JS, Koutsidis G, Dodson AT, Mottram DS, Wedzicha BL (2005) The effect of cooking on acrylamide and its precursors in potato, wheat and rye. Chem Safe Acr Food 561:255–269

    Article  CAS  Google Scholar 

  17. Fiselier K, Grob K (2005) Legal limit for reducing sugars in prefabricates targeting 50 mu g/kg acrylamide in French fries. Eur Food Res Technol 220:451–458

    Article  CAS  Google Scholar 

  18. Amrein TM, Andres L, Manzardo GGG, Amado R (2006) Investigations on the promoting effect of ammonium hydrogencarbonate on the formation of acrylamide in model systems. J Agric Food Chem 54:10253–10261

    Article  CAS  Google Scholar 

  19. Gokmen V, Acar OC, Koksel H, Acar J (2007) Effects of dough formula and baking conditions on acrylamide and hydroxymethylfurfural formation in cookies. Food Chem 104:1136–1142

    Article  Google Scholar 

  20. Zhang Y, Chen J, Zhang XL, Wu XQ, Zhang Y (2007) Addition of antioxidant of bamboo leaves (AOB) effectively reduces acrylamide formation in potato crisps and French fries. J Agric Food Chem 55:523–528

    Article  CAS  Google Scholar 

  21. Zhang Y, Xu WZ, Wu XQ, Zhang XL, Zhang Y (2007) Addition of antioxidant from bamboo leaves as an effective way to reduce the formation of acrylamide in fried chicken wings. Food Add Cont 24:242–251

    Article  Google Scholar 

  22. Zhu F, Cai YZ, Ke JX, Corke H (2009) Evaluation of the effect of plant extracts and phenolic compounds on reduction of acrylamide in an asparagine/glucose model system by RP-HPLC-DAD. J Sci Food Agric 89:1674–1681

    Article  CAS  Google Scholar 

  23. Bassama J, Brat P, Bohuon P, Boulanger R, Gunata Z (2010) Study of acrylamide mitigation in model system: effect of pure phenolic compounds. Food Chem 123:558–562

    Article  CAS  Google Scholar 

  24. Kotsiou K, Tasioula-Margari M, Kukurova K, Ciesarova Z (2010) Impact of oregano and virgin olive oil phenolic compounds on acrylamide content in a model system and fresh potatoes. Food Chem 123:1149–1155

    Article  CAS  Google Scholar 

  25. Ou SY, Shi JJ, Huang CH, Zhang GW, Teng JW, Jiang Y, Yang BR (2010) Effect of antioxidants on elimination and formation of acrylamide in model reaction systems. J Hazard Mat 182:863–868

    Article  CAS  Google Scholar 

  26. Kotsiou K, Tasioula-Margari M, Capuano E, Fogliano V (2011) Effect of standard phenolic compounds and olive oil phenolic extracts on acrylamide formation in an emulsion system. Food Chem 124:242–247

    Article  CAS  Google Scholar 

  27. Zhu F, Cai YZ, Ke JX, Corke H (2011) Dietary plant materials reduce acrylamide formation in cookie and starch-based model systems. J Food Sci Agric 91:2477–2483

    Article  CAS  Google Scholar 

  28. Acar OC, Gokmen V (2009) Investigation of acrylamide formation on bakery products using a crust-like model. Mol Nutr Food Res 54:1521–1525

    Google Scholar 

  29. Gokmen V, Senyuva HZ (2006) A simplified approach for the kinetic characterization of acrylamide formation in fructose-asparagine model system. Food Add Cont 23:348–354

    Article  Google Scholar 

  30. Yuan YA, Shu C, Zhou B, Qi XL, Xiang JG (2011) Impact of selected additives on acrylamide formation in asparagine/sugar Maillard model systems. Food Res Int 44:449–455

    Article  CAS  Google Scholar 

  31. Robert F, Vuataz G, Pollien P, Saucy F, Alonso MI, Bauwens I, Blank I (2004) Acrylamide formation from asparagine under low-moisture Maillard reaction conditions. 1. Physical and chemical aspects in crystalline model systems. J Agric Food Chem 52:6837–6842

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Vural Gökmen.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hamzalıoğlu, A., Gökmen, V. Role of bioactive carbonyl compounds on the conversion of asparagine into acrylamide during heating. Eur Food Res Technol 235, 1093–1099 (2012). https://doi.org/10.1007/s00217-012-1839-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-012-1839-z

Keywords

Navigation