Abstract

AbstractThe high specificity and activity of lipoxygenase (EC 1.13.1.13) have not been widely exploited in commercial applications. An analytical application of substrate specificity is exemplified by the Canadian Food and Drug Official Method FA 59 for determining unisomerized linoleic acid in hydrogenated fats. An attractive potential application of lipoxygenase is the lipoxygenase oxidation of linoleic acid for conversion of a renewable resource into a valuable chemical intermediate. Hydroxy‐conjugated octadecadienoic acids (HCD) have been prepared by oxidation of a 10% soybean soapstock solution with an aqueous soy flour extract followed by reduction of the hydroperoxide. High yields and a 20‐min reaction time are features of this procedure. These laboratory‐scale experiments indicate that the processing cost to produce hydroxy‐conjugated octadecadienoic acids can be estimated at 21 cents per lb. This cost does not include the cost of the soapstock. The combined hydroxy, conjugated diene, and fatty acid groups in HCD give it the potential of being a versatile chemical intermediate. HCD is readily converted to hydroxystearate or conjugated triene and can compete directly with tung oil acids or hydrogenated castor oil acids. Other reactions can be visualized based on functional group modification to yield products with potential application in the formulation of coatings, lubricants, emulsifiers, and plasticizers.

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