The preparation of triglycerides highly enriched with ω-3 polyunsaturated fatty acids via lipase catalyzed interesterification

Haraldsson, Guđmundur G.; Höskuldsson, Páll A.; Sigurdsson, Snorri Th.; Thorsteinsson, Freygardur; Gudbjarnason, Sigmundur

doi:10.1016/s0040-4039(00)99550-9

Cited by 81 publications

(31 citation statements)

References 14 publications

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“…Lipozyme IM is an immobilized 1,3-regiospecific R. miehei fungal lipase commercially available from Novo Nordisk. It is known to display a good discrimination between EPA and DHA in favor of EPA (22), and became the lipase of choice.…”

Section: Resultsmentioning

confidence: 99%

Separation of eicosapentaenoic acid and docosahexaenoic acid in fish oil by kinetic resolution using lipase

Haraldsson

Kristinsson

1998

J Americ Oil Chem Soc

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The objective of this study was to investigate the use of lipases as catalysts for separating eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in fish oil by kinetic resolution. Transesterification of various fish oil triglycerides with a stoichiometric amount of ethanol by immobilized Rhizomucor miehei lipase under anhydrous solvent-free conditions resulted in a good separation. When free fatty acids from the various fish oils were directly esterified with ethanol under similar conditions, greatly improved results were obtained. By this modification, complications related to regioselectivity of the lipase and nonhomogeneous distribution of EPA and DHA into the various positions of the triglycerides were avoided. As an example, when tuna oil comprising 6% EPA and 23% DHA was transesterified with ethanol, 65% conversion into ethyl esters was obtained after 24 h. The residual glyceride mixture contained 49% DHA and 6% EPA (8:1), with 90% DHA recovery into the glyceride mixture and 60% EPA recovery into the ethyl ester product. When the corresponding tuna oil free fatty acids were directly esterified with ethanol, 68% conversion was obtained after only 8 h. The residual free fatty acids comprised 74% DHA and only 3% EPA (25:1). The recovery of both DHA into the residual free fatty acid fraction and EPA into the ethyl ester product remained very high, 83 and 87%, respectively. JAOCS 75, 1551-1556 (1998).

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Section: Resultsmentioning

confidence: 99%

Separation of eicosapentaenoic acid and docosahexaenoic acid in fish oil by kinetic resolution using lipase

Haraldsson

Kristinsson

1998

J Americ Oil Chem Soc

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“…Lipases have been employed for the enrichment of fish oil TG with n-3 concentrates by various transesterification reactions (11,12). The preparation of homogeneous TG that contain both EPA and DHA also has been described by direct esterification of glycerol with pure EPA and DHA as free acids as well as by interesterification of tributyrin with ethyl esters (EE) of pure EPA and DHA (13).…”

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confidence: 99%

The preparation of concentrates of eicosapentaenoic acid and docosahexaenoic acid by lipase‐catalyzed transesterification of fish oil with ethanol

Haraldsson

Kristinsson

Sigurdardottir

et al. 1997

J Americ Oil Chem Soc

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The objective of this study was to investigate the use of lipases as catalysts for producing concentrates of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) from fish oil as an alternative to conventional chemical procedures. Transesterification of fish oil with ethanol was conducted under anhydrous solvent-free conditions with a stoichiometric amount of ethanol. Among the 17 lipases tested, the results showed that Pseudomonas lipases had the highest activity toward the saturated and monounsaturated fatty acids in the fish oil, much lower activity toward EPA and DHA and, at the same time, good tolerance toward the anhydrous alcoholic conditions. With 10 wt% of lipase, based on weight of the fish oil triacylglycerol substrate (15% EPA and 9% DHA initial content), a 50% conversion into ethyl esters was obtained in 24 h at 20°C, in which time the bulk of the saturated and monounsaturated fatty acids reacted, leaving the long-chain n-3 polyunsaturated fatty acids unreacted in the residual mixture as mono-, di-, and triacylglycerols. This mixture comprised approximately 50% EPA + DHA. Total recovery of DHA and EPA was high, over 80% for DHA and more than 90% for EPA. The observed fatty acid selectivity, favoring DHA as a substrate, was most unusual because most lipases favor EPA.

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“…Either moderate amounts have been incorporated in fats which normally contain no polyunsaturated fatty acids or very small amounts, like groundnut oil (Sridhar and Lakshminarayana, 1992), or products highly enriched in polyunsaturated fatty acids are prepared (Li and Ward, 1992). Fish oils contain large amounts of polyunsaturated fatty acids and they are therefore suitable starting materials for further enrichment (Haraldsson et al, 1989;Haraldsson and Almarsson, 1991).…”

Section: Triglyceride Modificationmentioning

confidence: 99%

Enzyme-catalysed Lipid Modification

Adlercreutz

1994

Biotechnology and Genetic Engineering Reviews

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The preparation of triglycerides highly enriched with ω-3 polyunsaturated fatty acids via lipase catalyzed interesterification

Cited by 81 publications

References 14 publications

Separation of eicosapentaenoic acid and docosahexaenoic acid in fish oil by kinetic resolution using lipase

Separation of eicosapentaenoic acid and docosahexaenoic acid in fish oil by kinetic resolution using lipase

The preparation of concentrates of eicosapentaenoic acid and docosahexaenoic acid by lipase‐catalyzed transesterification of fish oil with ethanol

Enzyme-catalysed Lipid Modification

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