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Study of TAG ethanolysis to 2‐MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG
Author(s) -
Irimescu Roxana,
Iwasaki Yugo,
Hou Ching T.
Publication year - 2002
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/s11746-002-0573-8
Subject(s) - candida antarctica , chemistry , caprylic acid , lipase , yield (engineering) , monoacylglycerol lipase , ethanol , glyceride , rhizomucor miehei , chromatography , substrate (aquarium) , molar ratio , catalysis , triacylglycerol lipase , organic chemistry , enzyme , fatty acid , biochemistry , materials science , endocannabinoid system , receptor , oceanography , metallurgy , geology
Regiospecific ethanolysis of homogenous TAG with immobilized Candida antarctica lipase (Novozym 435) was studied using trioleoylglycerol (TO) as a model substrate. Optimization of the reactant weight ratio revealed that the 2‐MAG reaction yield increased when a larger amount of ethanol was used. These results suggested that Novozym 435 showed strict regiospecificity in an excess amount of ethanol. The process optimization (reaction temperature and reactant molar ratio) and a study of lipase specificity for various substrates were performed. Under the optimized conditions (ethanol/TO molar ratio=77∶1 and 25°C), 2‐monooleoylglycerol (2‐MO) was obtained in more than 98% content among glycerides of the reaction mixture and approximately 88% reaction yield in 4 h. The above reaction conditions were applied for ethanolysis of tridocosahexaenoylglycerol, trieicosapentaenoylglycerol, triarachidonoylglycerol, tri‐α‐linolenoylglycerol, and trilinoleoylglycerol. Reaction yields ranging from 71.9 to 93.7% were obtained in short reaction times (2.5 to 8 h). Purified (>98%) 2‐MO and 2‐monodocosahexaenoylglycerol (2‐MD) were reesterified with caprylic acid by immobilized Rhizomucor miehei lipase (Lipozyme IM) to afford symmetrical structured TAG. At a stoichiometric ratio of 2‐MAG/caprylic acid, 25°C and 2–5 mm Hg vacuum, the glyceride composition of the esterification mixture was approximately 95% 1,3‐dicapryloyl‐2‐oleoylglycerol (COC) at 4 h, and 96% 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol (CDC) at 4 h, and 96% 1,3‐dicapryloyl‐2‐docosahexaenoylglycerol (CDC) at 8 h. The regioisomeric purity of both COC and CDC was 100%.