Purification of specific structured lipids by distillation: Effects on acyl migration

Xu, Xuebing; Skands, A. R. H.; Adler‐Nissen, Jens

doi:10.1007/s11746-001-0331-y

Cited by 39 publications

(29 citation statements)

References 9 publications

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“…For nutritional concerns, SL should be processed at mild conditions, not only because SL contain essential polyunsaturated fatty acids, but also because acyl migration might occur for specific SL if harsh conditions are employed [7]. Specific SL mixtures produced from enzymatic acidolysis contain more than 50% medium and long-chain free fatty acids and are therefore not well applicable to conventional distillation.…”

Section: Introductionmentioning

confidence: 99%

“…Specific SL mixtures produced from enzymatic acidolysis contain more than 50% medium and long-chain free fatty acids and are therefore not well applicable to conventional distillation. Thus, severe acyl migration has been observed compared to the acyl migration occurring during the reaction stage [7][8]. The acyl migration was mainly due to the existence of diacylglycerols in the reaction mixture, which act as intermediates for the lipase-catalyzed reactions.…”

Section: Introductionmentioning

confidence: 99%

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Purification and deodorization of structured lipids by short path distillation

Jacobsen

Nielsen

et al. 2002

Eur. J. Lipid Sci. Technol.

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Purification and deodorization of structured lipids by short path distillationPurification of structured lipids (SL), produced from lipase-catalyzed acidolysis of rapeseed oil and capric acid, and deodorization of randomized SL, produced from chemical randomization of fish oil and tricaprin, were studied in a bench-scale short path distillation (SPD). SL obtained from enzymatic acidolysis usually contain a large proportion of medium-chain and long-chain free fatty acids. Two SPD steps have been applied for the removal of free fatty acids. Parameters such as evaporator temperature, feeding flow rate, stirring roller speed, and the content of free fatty acids (FFA) added to the starting materials were optimized with respect to FFA left in the product residuals and to tocopherol loss from the starting oil. Evaporator temperature and flow rate were optimized using response surface methodology and two models were obtained for the FFA content left and loss of tocopherols. An applicable parameter zone was created to obtain a certain FFA (0.5% for example) content.In general, conditions that result in a lower FFA content will lead to a higher loss of tocopherols. In most parts of the parameter zone, 50% loss of tocopherols will be expected. The deodorization study of randomized SL from fish oils and tricaprin indicated that SPD in comparison with batch deodorization gave a product of a poorer sensoric quality. † Fatty acid composition after short path distillation to remove free fatty acids. The data in parenthesis is the fatty acid composition of acylglycerols before short path distillation (after reaction). ‡ After chemical randomization and before deodorization.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Purification and deodorization of structured lipids by short path distillation

Jacobsen

Nielsen

et al. 2002

Eur. J. Lipid Sci. Technol.

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“…Two TAG regioisomers, which have the same FA composition and carry a functional FA at the 1(3)-and 2-position, are necessary in order to study this subject. The two regioisomers have been synthesized by transesterification of long-chain TAG (LLL) with medium-chain FA (MCFA) using a 1,3-position-specific lipase and by transesterification of medium-chain TAG (MMM) with long-chain FA (LCFA) (1)(2)(3)(4)(5)(6)(7)(8)(9). The products can reportedly be purified by HPLC (10,11).…”

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confidence: 99%

Preparation of regioisomers of structured TAG consisting of one mole of CLA and two moles of caprylic acid

Kawashima

Nagao

Watanabe

et al. 2004

J Americ Oil Chem Soc

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TAG (MLM) with medium-chain FA (MCFA) at the 1,3-positions and long-chain FA (LCFA) at the 2-position, and TAG (LMM) with LCFA at the 1(3)-position and MCFA at 2,3(1)-positions are a pair of TAG regioisomers. Large-scale preparation of the two TAG regioisomers was attempted. A commercially available FFA mixture (FFA-CLA) containing 9-cis,11-trans (9c,11t)-and 10t,12c-CLA was selected as LCFA, and caprylic acid (C 8 FA) was selected as MCFA. The MLM isomer was synthesized by acidolysis of acylglycerols (AG) containing two CLA isomers with C 8 FA: A mixture of AG-CLA/C 8 FA (1:10, mol/mol) and 4 wt% immobilized Rhizomucor miehei lipase was agitated at 30°C for 72 h. The ratio of MLM to total AG was 51.1 wt%. Meanwhile, LMM isomer was synthesized by acidolysis of tricaprylin with FFA-CLA: A mixture of tricaprylin/FFA-CLA (1:2, mol/mol) and 4 wt% immobilized R. miehei lipase was agitated at 30°C for 24 h. The ratio of LMM to total AG was 51.8 wt%. MLM and LMM were purified from 1,968 and 813 g reaction mixtures by stepwise short-path distillation, respectively. Consequently, MLM was purified to 92.3% with 49.1% recovery, and LMM was purified to 93.2% with 52.3% recovery. Regiospecific analyses of MLM and LMM indicated that the 2-positions of MLM and LMM were 95.1 mol% LCFA and 98.3 mol% C 8 FA, respectively. The results showed that a process comprising lipase reaction and short-path distillation is effective for large-scale preparation of high-purity regiospecific TAG isomers.Much attention has been focused on the effect of position of FA in TAG on physiological activities. Two TAG regioisomers, which have the same FA composition and carry a functional FA at the 1(3)-and 2-position, are necessary in order to study this subject. The two regioisomers have been synthesized by transesterification of long-chain TAG (LLL) with medium-chain FA (MCFA) using a 1,3-position-specific lipase and by transesterification of medium-chain TAG (MMM) with long-chain FA (LCFA) (1-9). The products can reportedly be purified by HPLC (10,11). The process comprising lipase reaction and HPLC is effective for preparing high-purity TAG regioisomers, and the products have been used for examining the intestinal absorption of TAG (12). However, animal tests involving oral administration require larger amounts of TAG regioisomers, and the purification process by HPLC is not suitable for large-scale preparation. Xu and colleagues (7,8) carried out large-scale preparation of TAG regioisomers by short-path distillation, but the resulting preparations were mixtures of MMM, MLM, and MLL because the distillation removed only FFA. Negishi et al. (9) purified MLM from the reaction mixture, but the content of MLM was only 76%. For these reasons, a process for preparing larger amounts of pure TAG regioisomers (purity >90%) is strongly desired.TAG (MLM) with MCFA at the 1,3-positions and LCFA at the 2-position, and TAG (LMM) with LCFA at the 1(3)-position and MCFA at the 2,3(1)-positions, represent a pair of TAG regioisomers. To evaluate nutritional effects ...

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“…However after prolonged reaction, with the formation of 1,3-DAG, acyl migration occurred that permit some randomization of the sn-2 position fatty acids in the TAG backbone 6 . The factors of acyl migration were reaction time, reaction temperature, presence of water, reactor type and reaction system 21,22 . In other words, the specificity performance of enzyme is very dependent on the reaction system and conditions, as they can only perform their specificity under particular conditions 10,11 .…”

Section: Positional Analysismentioning

confidence: 99%