Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 1/15/2004
Publication Date: 5/1/2004
Citation: Foglia, T.A., Jones, K.C., Lee, K. 2004. Synthesis of structured lipids: enzymatic vs. chemical approaches [abstract]. 95th Annual Meeting of the American Oil Chemists' Society. p. 13-14.
Technical Abstract: Mixed medium and long-chain triacylglycerol structured lipids intended as low-calorie triacylglycerol products were synthesized by either lipase-catalyzed or chemical syntheses. In the lipase-catalyzed reactions, stearic acid was selectively incorporated at the 1 and 3 positions of tributyrin using a 1,3-positionally selective lipase (Rhizomucor meihei). At 10% of lipase (w/w of substrates), the acidolysis reaction reached equilibrium within 3 to 6 h at 70°C depending on the substrate mole ratio used. After purification and isolation by column chromatography, the products were analyzed by high performance liquid chromatography, which showed the products were composed of two types of triacylglycerols. One species contained two butyryl and one stearoyl acyl residues (45% to 85%) and the second contained one butyryl and two stearoyl acyl residues (14% to 55%) the ratio of which depended on the molar ratio of substrates used. For the chemical reaction, tributyrin was transesterified with methyl stearate using sodium methoxide as catalyst (0.25% w/w of substrates). Unlike the enzyme produced structured lipid product, the ratio of the triacylglycerol species did not vary with the mole ratio of reactants used in transesterification. The purified MLCT products were further analyzed by differential scanning calorimetry to compare their crystallization patterns.