Stearidonic Acid Concentration by Urea Complexation from Echium Oil.

Concentration of polyunsaturated fatty acids ethyl esters (FAEE) by urea complexation from Echium oil was studied. Different variables involved in the process were investigated: amount and particle size of urea, solvent volume and ratio (hexane/ethanol), load of FAEE and reaction time. Hence, the main goal was to optimize SDA concentration (%) and yield (%) of stearidonic acid (SDA, 18:4 ω-3) and other bioactive FAEE. Similar behaviors were observed in fractionation between α-linolenic (ALA)-linoleic (LA), and γ-linolenic (GLA)-stearidonic (SDA) acids, attributed to similarities on their chemical structures, due to the position of the double bonds. At laboratory scale, the optimal conditions were 3 g urea (powder), 3.6 mL of hexane, 0.54 mL of ethanol and 800 mg of FAEE, during 20 h at 25°C. A scaling-up at pilot plant was carried out twice, obtaining more than 100 g of a final product, with ~29% SDA concentration and ~78% yield. Besides, after two washings with water, ethyl carbamates (urethanes) were not detected in the final product. Thus, a mixture of FAEE with about 85% of bioactive fatty acids with anti-inflammatory properties was obtained, which can be a high added-value product with great potential for the synthesis of functional lipids and nutraceuticals.