Amine degradation by 4,5-epoxy-2-decenal in model systems

Journal of Agricultural and Food Chemistry
Rosario ZamoraFrancisco J Hidalgo

Abstract

The reactions of 4,5-epoxy-2-decenal with octylamine, benzylamine, and 2-phenylglycine methyl ester were studied to investigate if amines may suffer a Strecker type degradation by epoxyalkenals analogously to amino acids. In addition to other reactions, the studied amines were converted into their corresponding Strecker aldehydes (octanal, benzaldehyde, and methyl 2-oxo-2-phenylacetate, respectively) to an extent that depended on the pH, the temperature, the amount of epoxyalkenal, and the amine involved. Each amine exhibited an optimum pH for the reaction, but the corresponding Strecker aldehydes were produced to a significant extent within a broad pH range. In addition, the temperature mostly influenced the reaction rate, which was increased between 6.5 and 9.5 times when the reaction was carried out at 60 degrees C than when it took place at 37 degrees C. Furthermore, Strecker aldehyde formation was linearly correlated with the amount of the epoxyalkenal present in the reaction mixture. Nevertheless, the reaction yield mostly depended on the amine involved. Thus, octylamine only produced trace amounts of octanal, benzylamine was converted into benzaldehyde with a yield of 4.3%, and 2-phenylglycine methyl ester was converted ...Continue Reading

References

Jan 1, 1993·Chemical Research in Toxicology·L M SayreR G Salomon
Dec 20, 1999·Journal of Agricultural and Food Chemistry·R ZamoraF J Hidalgo
Jun 20, 2000·Chemical Research in Toxicology·F J Hidalgo, R Zamora
Dec 19, 2003·Chemical Research in Toxicology·Rosario Zamora, Francisco J Hidalgo
Jan 7, 2004·Journal of Agricultural and Food Chemistry·Rosario Zamora, Francisco J Hidalgo
Jun 24, 2004·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
Feb 22, 2005·Chemical Research in Toxicology·Rosario Zamora, Francisco J Hidalgo
Feb 26, 2005·Critical Reviews in Food Science and Nutrition·Rosario Zamora, Francisco J Hidalgo
Mar 3, 2005·Journal of Agricultural and Food Chemistry·Sweetie R KanattArun Sharma
Mar 17, 2005·Journal of Agricultural and Food Chemistry·Kaarina ViljanenMarina Heinonen
May 26, 2005·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo

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Citations

May 15, 2012·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
Aug 9, 2007·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Francisco J HidalgoRosario Zamora
Jun 27, 2015·Chemico-biological Interactions·Ryo TakahashiSeon Hwa Lee
Mar 10, 2015·Critical Reviews in Food Science and Nutrition·Francisco J Hidalgo, Rosario Zamora
Aug 19, 2008·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
Dec 30, 2014·Journal of Agricultural and Food Chemistry·Rosa M DelgadoFrancisco J Hidalgo
Jul 16, 2008·Journal of Agricultural and Food Chemistry·Rosario Zamora, Francisco J Hidalgo

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