Hidalgo Francisco J, Aguilar Isabel, Zamora Rosario
Instituto de la Grasa, Consejo Superior de Investigaciones Científicas , Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.
J Agric Food Chem. 2017 Jun 14;65(23):4736-4743. doi: 10.1021/acs.jafc.7b01081. Epub 2017 Jun 1.
The reaction among flavor-relevant saturated aldehydes (propanal, 2-methylpropanal, butanal, 2-methylbutanal, 3-methylbutanal, pentanal, hexanal, and glyoxal) and phenolic compounds (resorcinol, 2-methylresorcinol, 2,5-dimethylresorcinol, and orcinol) was studied both to identify and to characterize the formed carbonyl-phenol adducts and to understand the differences in the carbonyl-trapping abilities of phenolic compounds. The obtained results showed that carbonyl-trapping by phenolics is selective and that the formation of carbonyl-phenol adducts depends on the structures of both the phenol and aldehyde involved. In relation to the phenolic derivative, the presence of groups that increase the nucleophilicity of phenolic carbons will increase the carbonyl-trapping ability of these compounds. On the other hand, the presence of groups that increase the steric hindrance of these positions without affecting nucleophilicity will inhibit the reaction. Analogously, the presence of branching at position 2 of the aldehyde will also inhibit the reaction by steric hindrance. All of these results suggest that the addition of phenolics to foods may change food flavor not only because of their sensory properties but also because they can modify the ratio among food odorants by selective reaction of phenolics with determined carbonyl compounds.
研究了与风味相关的饱和醛（丙醛、2-甲基丙醛、丁醛、2-甲基丁醛、3-甲基丁醛、戊醛、己醛和乙二醛）与酚类化合物（间苯二酚、2-甲基间苯二酚、2,5-二甲基间苯二酚和邻苯二酚）之间的反应，以鉴定和表征形成的羰基-酚加合物，并了解酚类化合物在羰基捕获能力方面的差异。所得结果表明，酚类化合物对羰基的捕获具有选择性，羰基-酚加合物的形成取决于所涉及的酚和醛的结构。就酚类衍生物而言，增加酚类碳亲核性的基团的存在将提高这些化合物的羰基捕获能力。另一方面，在不影响亲核性的情况下增加这些位置空间位阻的基团的存在将抑制反应。类似地，醛的2位存在支链也会因空间位阻而抑制反应。所有这些结果表明，向食品中添加酚类化合物可能会改变食品风味，这不仅是因为它们的感官特性，还因为它们可以通过酚类化合物与特定羰基化合物的选择性反应来改变食品气味剂之间的比例。
