Properties of conjugated Schiff bases of malonaldehyde.

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Abstract
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 compounds I5 produced as intense a red color as malonaldehyde. Compounds I1-I4 were active as antioxidants with methyl oleate, lard and soybean oil.