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Lipase‐Catalyzed Synthesis of d ‐Psicose Fatty Acid Diesters and their Emulsification Activities
Author(s) -
Afach Ghanwa,
Kawanami Yasuhiro,
Cheetangdee Nopparat,
Fukada Kazuhiro,
Izumori Ken
Publication year - 2008
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-008-1242-x
Subject(s) - candida antarctica , chemistry , monoglyceride , lipase , emulsion , fatty acid , interesterified fat , glyceride , organic chemistry , chromatography , enzyme
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.