Preparation of trehalose and sorbitol fatty acid polyesters by interesterification

Trehalose octaoleate and sorbitol hexaoleate were prepared by a one-stage solvent-free interesterification of methyl oleate with trehalose octaacetate (TOAC) and sorbitol hexaacetate (SOHA), respectively, in the presence of 1–2.5% sodium metal as catalyst. The greatest yield of trehalose octaoleate, 97.5%, and sorbitol hexaoleate, 96.0%, were obtained at a mole ratio of methyl oleate: SOHA of 6:1 and methyl oleate:TOAC of 8:1 at a synthesis time of 2.5 hr, and temperatures of 105–115°C. The structure of both trehalose octaoleate and sorbitol hexaoleate was confirmed by infrared (IR) and nuclear magnetic resonance (C-13 NMR) spectroscopy. Physical properties such as viscosity, HLB, solubility, color, refractive index, specific gravity and density approximated the physical properties of sucrose polyesters (SPE) and vegetable oils. Trehalose octaoleate and sorbitol hexaoleate, as well as sucrose octaoleate, were not susceptible toin vitro lipolysis, suggesting potential application as low calorie oils. Presented at American Oil Chemists’ Society Annual Meeting in New Orleans, LA, in May, 1987.