Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: February 15, 2006
Publication Date: April 30, 2006
Citation: Piazza, G.J., Foglia, T.A. 2006. Synthesis of fatty acid epoxides from vegetable oils and fats using enzymes in oat seeds [abstract]. Annual Meeting and Expo of the American Oil Chemists' Society. p. 73. Technical Abstract: Oat seeds contain lipase and peroxygenase enzymes that are potentially useful for the modification of fats and oils and their derivatives. We have investigated the use of ground oat seeds as an inexpensive carrier of these enzymes for the chemical modification of oils and fats. We found that, in the presence of calcium chloride or the surfactant deoxycholate, triacyglycerols are hydrolyzed to their constituent fatty acids and glycerol in both aqueous media and in organic media consisting of non-polar organic solvent such as hexane. The release of fatty acids was monitored directly using HPLC with ELSA detection. In the pH range of 7-9, 80% of the fatty acids were liberated in 24 h reactions. Only minor amounts of di- and mono-acylglycerols were produced. When the oxidant t-butyl hydroperoxide (TBHP) was added to the reaction media, approximately 35% of the unsaturated fatty acids were converted to their epoxide derivatives in the presence of deoxycholate at pH values 6 and 7, whereas in the presence of calcium chloride only 20% of the fatty acids were converted to epoxides. No epoxidized tri-, di-, or monoacylglycerols were detected. A new polar compound was detected in the presence of deoxycholate and TBHP which constituted up to 15% of the product. The chemical structure of this product is currently under investigation. To obtain the highest yield of epoxidized fatty acids, it was determined that from 1.4 to 2.8 times TBHP per amount of fatty acid in the triacylglycerol oil was needed.