Abstract
The effectiveness of different compounds in the generation of acrylamide (AA) from asparagine, was determined by reacting asparagine with mono-, diand polysaccharides, as well as four different oxo-compounds known to be involved in carbohydrate metabolism/degradation. Quantitation of AA formed either under aqueous conditions or in low water model systems revealed glucose and 2-oxopropionic acid as the most effective compounds in AA generation, when reacted in model systems with a low water content (about 1 mol-% yield). Interestingly, heating of asparagine in the presence of 2-oxopropionic acid generated quite high amounts of 3-aminopropionamide (3-APA), which itself effectively generated AA upon heating in aqueous solution, as well as in low water systems. Because this is the first report on amounts of 3-APA generated by Maillard-type reactions, the general role of 3-APA as key intermediate in AA formation is discussed in detail. In addition, first results on the development and application of an HPLC/fluorescence method for AA quantitation are presented.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Becalski, A., Lau, B. P.-Y., Lewis, D., and Seaman, S., 2003, Acrylamide in food: Occurrence, sources, and modeling, J. Agric. Food Chem. 51:802–808.
Granvogl, M., Jezussek, M., Koehler, P., and Schieberle, P., 2004, Quantitation of 3-Aminopropionamide in Potatoes-A Minor but Potent Precursor in Acrylamide Formation, J. Agric. Food Chem. 52:4751–4757.
Hofmann, T., and Schieberle, P., 2000, Formation of aroma-active Strecker-aldehydes by a direct oxidative degradation of Amadori compounds, J. Agric. Food Chem. 48:4301–4305.
Jezussek, M., and Schieberle, P., 2003, A new LC/MS-method for the quantitation of acrylamide based on a stable isotope dilution assay and derivatization with 2-mercaptobenzoc acid. Comparison with two GC/MS-methods, J. Agric. Food Chem. 51:7866–7871.
Mottram, D. S., Wedzicha, B. L., and Dodson, A. T., 2002, Food chemistry: Acrylamide is formed in the Maillard reaction, Nature 419:448–449.
Stadler, R. H., Blank, I., Varga, N., Robert, F., Hau, J., Guy, P. A., Robert, M.-C., and Riediker, S., 2002, Food chemistry: Acrylamide from Maillard reaction products, Nature 419:449–450.
Stadler, R. H., Robert, F., Riediker, S., Varga, N., Davidek, T., Devaud, S., Goldmann, T., Hau, J., and Blank, I., 2004, In-depth mechanistic study on the formation of acrylamide and other vinylogous compounds by the Maillard reaction, J. Agric. Food Chem. http://dx.doi.org/10.1021/jf0495486.
Tareke, E., Rydberg, P., Karlsson, P., Eriksson, S., and Törnqvist, M., 2002, Analysis of acrylamide, a carcinogen in heated foodstuffs, J. Agric. Food Chem. 50:4998–5006.
Weisshaar, R., and Gutsche, V., 2002, Formation of acrylamide in heated potato products — model exeperiments pointing to asparagine as precursor, Deutsche Lebensm. Rund. 98:397–400.
Yaylayan, V. A., Wnorowski, A., and C.P., L., 2003, Why asparagine needs carbohydrates to generate acrylamide, J. Agric. Food Chem. 51:1753–1757.
Zyzak, D. V., Sanders, R. A., Stojanovic, M., Tallmadge, D. H., Eberhart, B. L., Ewald, D. K., D.C., G., Morsch, T. R., Strothers, M. A., Rizzi, G. P., and Villagran, M. D., 2003, Acrylamide formation mechanism in heated foods, J. Agric. Food Chem. 51:4782–4787.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2005 Springer Science+Business Media, Inc.
About this paper
Cite this paper
Schieberle, P., Köhler, P., Granvogl, M. (2005). New Aspects on the Formation and Analysis of Acrylamide. In: Friedman, M., Mottram, D. (eds) Chemistry and Safety of Acrylamide in Food. Advances in Experimental Medicine and Biology, vol 561. Springer, Boston, MA. https://doi.org/10.1007/0-387-24980-X_16
Download citation
DOI: https://doi.org/10.1007/0-387-24980-X_16
Publisher Name: Springer, Boston, MA
Print ISBN: 978-0-387-23920-0
Online ISBN: 978-0-387-24980-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)