Preparation and properties of fully esterified erythritol

Abstract

Pure tetraesters of erythritol with C 10 , C 12 , C 14 , C 16 , C 18 saturated, and C 18:1 unsaturated (oleoyl) fatty acyl chains have been prepared for the first time and characterized using the acylating systems fatty acid/ N,N 0 -dicyclohexylcarbodiimide/4-dimethylaminopyridine (DMAP), fatty acid anhydride/DMAP, fatty acyl chloride/pyridine, and fatty acyl chloride/boron trifluoride etherate. For the first three systems the yields were in the range of 80-90% while the fatty acyl chloride/pyridine system has the advantage of lower cost. The fatty acyl chloride/boron trifluoride etherate system gave lower (ca 70%) yields of the tetraesters. The tetraesters of erythritol may have applications analogues to those of triglycerides. In addition, new applications can be envisaged for these compounds, as a result of their differences in physical, chemical, and biochemical properties compared to triglycerides. Practical applications:The tetraesters of erythritol with saturated fatty acyl chains may have applications analogous to those of saturated triglycerides. However, tetraesters with unsaturated fatty acid chains may have greater prospects of having industrial uses after doing chemistry on the carbon-carbon double bonds.

Kinetic Analysis of the Lipase-Catalyzed Hydrolysis of Erythritol and Pentaerythritol Fatty Acid Esters: A Biotechnological Application for Making Low-Calorie Healthy Food Alternatives

“…Argon of high purity (≥99.99%) was purchased from Linde Hellas Ltd. (Linde Group). The herein utilized tetraesters, i.e., erythritol tetraoleate, erythritol tetrapalmitate, erythritol tetralaurate, pentaerythritol tetrapalmitate, and pentaerythritol tetrastearate, were synthesized as described previously [6]. Because the yield of pentaerythritol tetrapalmitate, obtained from the acylation of pentaerythritol by palmitoyl chloride in the presence of BF 3 •Et 2 O, was only 47% [6], we describe in the Supplementary Materials the RCOCl/pyridine method for acylation, which gave 90% yield.…”

“…This work comprises a detailed kinetic study of the lipase-catalyzed hydrolysis of three fatty acid tetraesters of erythritol and two tetraesters of pentaerythritol. These five tetraesters have the potential for being biotechnologically useful in food and in cosmetics applications as compared to the triesters of glycerol [6]. All five studied tetraesters herein were hydrolyzed by two lipases, which contain similar catalytic triads (S 152 /S 105 , H 263 /H 224 , D 176 /D 187 ), namely, porcine pancreatic lipase (PPL) and Candida antarctica lipase-B (CALB).…”