From an interfacial phenomena standpoint, the effect of length of alkyl
chain was evaluated on activities of gallic acid and its alkyl ester
derivatives in supramolecular oxidation of stripped soybean oil. The
gallic acid molecules (log P = -0.47) with an electron-donating
carboxylate anion had a higher scavenging activity against DPPH• than
alkyl gallates. Interfacial activities of gallates in emulsion and bulk
oil improved as the lengths of the alkyl chain were reached until a
critical chain length; after that, further chain length extension causes
a decrease in potency. In β-carotene bleaching and Rancimat assays
higher inhibitory effect was observed for dodecyl and propyl gallate,
respectively. Evaluation of interfacial tension, water content, and
droplet size of hydroperoxides reverse micelles in parallel with lipid
peroxidation indicated that the inhibitory effect of the alkyl gallates,
especially methyl gallate, was significantly better than the gallic acid
in the bulk phase oil.