Lipase‐Catalyzed Synthesis of d‐Psicose Fatty Acid Diesters and their Emulsification Activities

• Published in: Journal of the American Oil Chemists' Society
• Main Authors: Afach, Ghanwa, Kawanami, Yasuhiro, Cheetangdee, Nopparat, Fukada, Kazuhiro, Izumori, Ken
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2008
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1007/s11746-008-1242-x; https://onlinelibrary.wiley.com/doi/full/10.1007/s11746-008-1242-x

Abstract The diesterification of d ‐psicose (the C‐3 epimer of d ‐fructose) with fatty acid vinyl esters of selected acyl chain lengths (C 8 , C 10 , and C 12 ) was successfully carried out using Candida antarctica lipase (Novozym 435) at 45 °C for 24 h to give the 1,6‐diacyl‐ d ‐psicofuranoses with a high regioselectivity in good yields (83–90%). These diesters of d ‐psicose have hydrophilic‐lipophilic balance (HLB) values (6.5–8.2) similar to HLB values of monoglyceride compounds which constitute the largest single type of emulsifiers employed by the food industry. Ability of the d ‐psicose diesters to stabilize oil‐in‐water emulsions and the weight‐averaged oil‐droplet diameter in the emulsions was evaluated in this study. Emulsion stability of oil droplets stabilized by d ‐psicose dicaprylate (0.3%, w/v in oil phase) was comparable to d ‐fructose dicaprylate (0.2%, w/v). It was further confirmed that the d ‐psicose diesters exhibited an emulsification activity depending on the chain length of fatty acid; d ‐psicose dicaprate showed better emulsion stability than the other diesters.