Raffinose esters of long-chain unsaturated fatty acids: Preparation, characterization, and in vitro digestive behavior.

This study synthesized raffinose monoesters with polyunsaturated fatty acids (PUFA) including oleic acid, linolenic acid, and eicosapentaenoic acid through chemical synthesis. The HLB values of monoesters ranged from15.2 to16.7. Emulsions stabilized by monoesters exhibited exceptional stability over a 16-day period (50-90 °C), with the average diameter varying by less than ±30 nm. The PV values of three monoesters changed by less than 0.07. During in vitro simulated digestive model, the FA release rate exceeded 72.2 % in emulsions. However, the monoesters with lower chain length, higher saturation correlated with faster hydrolysis in gastric phase. At the intestinal stage, digestion rate was predominantly mediated by lipase, showing a trend opposite to that in the stomach. These findings confirmed that monoesters could be digested, thereby increased bioavailability and stability of PUFA. These novel raffinose monoesters offered a new approach to promoting the application of PUFA as a functional supplement.