Formation of acrolein from various amino-acids and polyamines under degradation at 100°C

Abstract

The formation of acrolein from several new sources under common and widely used physico-chemical conditions is quantitatively reported. Methionine, homoserine, homocysteine, and cystathionine in decreasing order, generated significant amounts of acrolein in aerobic interactions at neutral pH and 100°C with compounds capable of producing the Strecker degradation of α-amino acids. Such decarboxylation and oxidative deamination of the above amino acids would result in 3-substituted propanals, structures which according to previous studies readily decompose with the formation of acrolein. Interactions of spermine and related polyamines with these agents, H 2O 2, or with photoactivated riboflavin, also resulted in the formation of acrolein. Hydrogen peroxide, for example, the most effective single degrading agent tested, produced 2.5 and 4.1 μmole of acrolein (50 and 82%) yield), in 1 hour or less, from 5 μmole of methionine and spermine, respectively. In all of these reactions, the presence of oxygen was essential. Methional, the 3-substituted propanal derived from methionine, however, easily decomposed with formation of acrolein both in the presence and in the absence of oxygen. The formation of acrolein in significant amounts in these reactions, together with its highly toxic properties appears to indicate that this aldehyde may play a more important role as an environmental contaminant than has heretofore been suspected.