Direct and selective enzymatic synthesis of trehalose unsaturated fatty acid diesters and evaluation of foaming and emulsifying properties

Abstract

Trehalose diesters are Gemini-type surfactants that might have better surface activity than conventional surfactants. A one-step method for the preparation of trehalose unsaturated fatty acid diesters has been successfully developed. The yield of trehalose diester of different unsaturated fatty acids was between 78 % and 88 % under optimal conditions: 25 mmol/L trehalose, 100 mmol/L unsaturated fatty acid, 60 g/L 3 Å molecular sieves and 20 g/L lipase at 150 rpm and 50 °C for 42 h in 15 mL of acetone. Additionally, trehalose diester was the sole product obtained with Novozym 435 in acetone. The chemical structures of 6,6′-di-O-oleoyltrehalose, 6,6′-di-O-linoleoyltrehalose, 6,6′-di-O-eicosenoyltrehalose and 6,6′-di-O-erucoyltrehalose were confirmed by FTIR, MS and NMR. Moreover, the hydrophile-lipophile balance (HLB) values, foaming properties and emulsifying properties of trehalose diesters were assessed, showing the potentials of these diesters as naturally derived surfactants for the food industry.