Malonaldehyde is one of the end products of lipid oxidation, and because of its bifunctionality it can produce a conjugated Schiff base with a primary amine. The fluorescence properties, the reactivity to thiobarbituric acid (TBA) and the antioxidative activity of conjugated Schiff bases of malonaldehyde and aniline (I1), p-toluidine (I2), p-anisidine (I3), p-chloroaniline (I4) and p-aminoacetophenone (I5) were investigated. Compounds I1-I5 showed no significant intrinsic fluorescence. The unstable compound I5 produced highly fluorescent compound(s) in a mixture of dimethylformamide-tetra-n-propylammonium hydroxide. In the TBA reaction, compounds I1-I4 produced less than 30% as much a red color as malonaldehyde, while the unstable compound I5 produced as intense a red color as malonaldehyde. Compounds I1-I4 were active as antioxidants with methyl oleate, lard and soybean oil.
丙二醛是脂质氧化的最终产物之一,由于它具有双功能性,因此可以与
伯胺生成共轭席夫碱。研究了
丙二醛与
苯胺(I1)、对甲
苯胺(I2)、对
甲氧基苯胺(I3)、
对氯苯胺(I4)和对
氨基
苯乙酮(I5)的共轭席夫碱的荧光特性、与
硫代
巴比妥酸(TBA)的反应性和抗氧化活性。化合物 I1-I5 没有显示出明显的内在荧光。不稳定的化合物 I5 在二甲基甲酰胺-四正丙基氢氧化
铵混合物中产生了高荧光化合物。在 TBA 反应中,化合物 I1-I4 产生的红色不及
丙二醛的 30%,而不稳定化合物 I5 产生的红色与
丙二醛一样强烈。化合物 I1-I4 与
油酸甲酯、猪油和大豆油一起作为
抗氧化剂具有活性。