Chemical conversion of phenylethylamine into phenylacetaldehyde by carbonyl-amine reactions in model systems

Journal of Agricultural and Food Chemistry
Rosario ZamoraFrancisco J Hidalgo

Abstract

The chemical conversion of phenylethylamine into phenylacetaldehyde in the presence of lipid oxidation products (LOPs) was studied to investigate the possibility that biogenic amines can be converted into Strecker aldehydes upon processing. Model systems of phenylethylamine and methyl 13-hydroperoxyoctadeca-9,11-dienoate (HP), 2,4-decadienal (DD), 4,5-epoxy-2-heptenal (EH), 4,5-epoxy-2-decenal (ED), 4-oxo-2-hexenal (OH), 4-oxo-2-nonenal (ON), or 4-hydroxy-2-nonenal (HN) were heated for 1 h at 180 °C and pH 3. Although HN and EH did not produce more phenylacetaldehyde than when phenylethylamine was heated alone, all other lipid oxidation products assayed increased the amount of phenylacetaldehyde produced by 300-900%, with ON being the most reactive compound for this reaction. The reaction was mainly produced at acidic pH values (<6) and was dependent upon the concentration of the LOPs involved, and the phenylacetaldehyde produced increased linearly as a function of the time and temperature. The E(a) values for the reactions between phenylethylamine and DD and ON were 54.8 and 53.8 kJ/mol, respectively. The reaction is proposed to take place by the formation of an imine between the phenylethylamine and the LOPs, which is later c...Continue Reading

References

Jun 20, 2000·Chemical Research in Toxicology·F J Hidalgo, R Zamora
Nov 13, 2004·Journal of Agricultural and Food Chemistry·Francisco J Hidalgo, Rosario Zamora
Mar 16, 2006·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
Feb 16, 2007·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
May 10, 2007·Journal of Agricultural and Food Chemistry·Francisco J Hidalgo, Rosario Zamora
May 2, 2008·Annals of the New York Academy of Sciences·Francisco J Hidalgo, Rosario Zamora
May 2, 2008·Annals of the New York Academy of Sciences·Fong Lam Chu, Varoujan A Yaylayan
Jul 16, 2008·Journal of Agricultural and Food Chemistry·Rosario Zamora, Francisco J Hidalgo
Oct 29, 2008·Journal of Agricultural and Food Chemistry·Fong Lam Chu, Varoujan A Yaylayan
Sep 12, 2009·Molecular Nutrition & Food Research·Rosario ZamoraFrancisco J Hidalgo
Sep 11, 2010·Journal of Agricultural and Food Chemistry·Francisco J HidalgoRosario Zamora
Mar 1, 2012·Critical Reviews in Food Science and Nutrition·Angela MarcobalRosario Muñoz
Mar 7, 2012·Journal of Agricultural and Food Chemistry·Christine M Mayr, Peter Schieberle

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