Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: September 9, 2004
Publication Date: October 1, 2004
Citation: Piazza, G.J., Foglia, T.A. 2004. Synthesis of a fatty tetrahydroxyamide using peroxygenase from oat seeds. Journal of the American Oil Chemists' Society. 81(10):933-937. Interpretive Summary: There is continuing interest in using fats and oils and their derivatives to produce biobased materials for industrial use. One area that is receiving increased attention is the controlled oxidation of fats to produce new materials that can be used as emulsifiers and surfactants. The current industrial procedure for oxidation is not easily controlled and uses a strong acid catalyst that is a potential pollutant, can cause equipment corrosion, and will degrade the product under some conditions. In addition the chemical structures of the oxidation products have been incompletely described. We have devised a biotechnological method to control the oxidation of several derivatives of fats and oils using a peroxygenase enzyme from oat seeds to replace the strong acid catalyst. We have characterized the products as epoxides and have reacted these epoxides with water in the presence of catalysts in a process termed hydrolysis to produce highly polar, water-mixible products. We found the hydrolysis of a fatty epoxide with a particular structure prepared from an amide derivative of linolenic acid generated an exceptionally polar material. This material exhibited exceptional affinity for metal surfaces, and thus, it may be useful in the formulation of metal cutting fluids.
Technical Abstract: Prior work has shown that oat (Avena sativa) seeds are a rich source of lipase and peroxygenase. Partial epoxidation of the isobutyl amide derivative of linolenic acid gave N-i-butyl-9,10-15,16-diepoxy-12(Z)-octadecenamide, a diepoxide product in which the epoxides reside only at the former external double bond positions. No amide hydrolysis occurred during the epoxidation procedure. Hydrolysis of the diepoxide gave N-i-butyl-9,10,15,16-tetrahydroxy-12(Z)-octadecenamide, a polyol derivative with relatively high polarity, potentially useful in developing new materials from fats and oils.