Ethoxyquin (EQ, 6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline) is widely used in animal feed in order to protect it against lipid peroxidation. EQ cannot be used in any food for human consumption (except spices, e.g., chili), but it can pass from feed to farmed fish, poultry, and eggs, so human beings can be exposed to this antioxidant. The manufacturer Monsanto Company (USA) performed a series of tests on ethoxyquin which showed its safety. Nevertheless, some harmful effects in animals and people occupationally exposed to it were observed in 1980's which resulted in the new studies undertaken to reevaluate its toxicity. Here, we present the characteristics of the compound and results of the research, concerning, for example, products of its metabolism and oxidation or searching for new antioxidants on the EQ backbone.
An environment-friendly, free of solvent, process for the synthesis of (R)- and (S)-ricinoleic acid amides has been developed. Starting from methyl ricinoleates and pyrrolidine or ethanolamine, the corresponding amides were obtained with yields ranging from 83-88%. Among 12 synthesized derivatives of ricinoleic acid, including the starting methyl esters, amides, and their acetates, nine compounds were obtained and tested for the first time. Studies on ricinoleic acid derivatives cytotoxicity showed that methyl esters were the least cytotoxic compounds and modification of their structure resulted in increasing cytotoxicity of the obtained products against both cancer cells and normal lymphocytes. Both enantiomers of the ethanolamine-derived amides showed the most promising anticancer potential.
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