A facile synthesis of aminohydroxy triglycerides from new crop oils

Vegetable oils as the main source of plant lipids are currently generating much interest as renewable industrial feedstocks for nonfood industrial applications both as biobased lubricants and biodiesel fuels. But of particular interest for us is use of new crop oils in novel industrial applications. These oils, in general, are glyceryl esters with olefinic bonds, which are readily functionalizable. Aminated lipids are important intermediates in many applications including pharmaceutical formulations because they have a modifying effect on cell membranes. We have exploited the nucleophilic property of the carbon-carbon double bonds in two seed oils to generate the oxirane derivatives of the lipids. Ring opening of the epoxy intermediates with amines under anhydrous ZnCl₂ catalysis is facile, and the reaction proceeds smoothly at moderate temperatures to given the aminohydroxy TG of milkweed and salicornia oils.