Lipase-Catalyzed Synthesis of d-Psicose Fatty Acid Diesters and their Emulsification Activities |
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Authors: | Ghanwa Afach Yasuhiro Kawanami Nopparat Cheetangdee Kazuhiro Fukada Ken Izumori |
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Affiliation: | (1) Rare Sugar Research Center, Kagawa University, 2393 Miki-cho, Kagawa 761-0795, Japan;(2) Department of Applied Biological Science, Faculty of Agriculture, Kagawa University, 2393 Miki-cho, Kagawa 761-0795, Japan |
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Abstract: | The diesterification of d-psicose (the C-3 epimer of d-fructose) with fatty acid vinyl esters of selected acyl chain lengths (C8, C10, and C12) 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. |
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Keywords: | d-psicose" target="_blank">d-psicose Sugar fatty acid ester Candida antarctica lipase Interfacial tension Emulsion stability |
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