Design and synthesis of 1,3-dicapryloyl-2-acetylglycerol as molecular probe for triacylglycerol metabolism study

Abstract

The increasing number of health issues caused by obesity and lack of healthy and efficient fat substitutes require development on new fat substitute. This study proposes a new potential reduced-calorie structured triacylglycerol (TAG) of “1,3-medium-chain, 2-short-chain triglycerides (MSM)” configuration, and the fat substitution method is based on the suppression of 2-monoacylglycerol absorption into intestinal cells, which would decrease the recombination of TAG and reduce lipid absorption in the digestive tract. A molecular probe, 1,3-dicapryloyl-2-acetylglycerol, is offered for nutritionists to conduct further study on its metabolism in human body. The synthesis method for this structured TAG starts from the lipase-catalyzed esterification between glycerol and caprylic acid, yielding 1,3-dicapryloylglycerol, and is followed by direct esterification with acetic anhydride to form 1,3-dicapryloyl-2-acetylglycerol. Its structure is characterized by FTIR,1H NMR,13C NMR, and LC-ESI-MS.