Lipase-catalyzed interesterification of soybean oil with an omega-3 polyunsaturated fatty acid concentrate prepared from sardine oil.
To reduce the content of linoleoyl moiety in soybean oil, soybean oil that contains 53.0% linoleoyl moiety as molar acyl moiety composition was interesterified with an omega-3 polyunsaturated fatty acid (PUFA) concentrate (24.0 mol% eicosapentaenoic acid [EPA], 40.4 mol% docosahexaenoic acid [DHA]) prepared from sardine oil, using an immobilized sn-1,3-specific lipase from Rhizomucor miehei (Lipozyme IM). The reaction was carried out in a batch reactor at 37 degrees C under the following conditions: 500 micromol of soybean oil, molar ratio of omega-3 PUFA concentrate to soybean oil = 1.0-6.0,5.0 mL of heptane, and 30 batch interesterification units of enzyme. After the reaction time of 72 h, modified soybean oil, which contains 34.9% linoleoyl, 10.1% eicosapentaenoyl, and 14.2% docosahexaenoyl moieties, was produced at the molar reactant ratio of 6.0. In this oil, the total omega-3 acyl moiety composition reached 34.1%; the molar ratio of omega-3 to omega-6 acyl moieties was enhanced by five times compared with soybean oil. Compared with palmitic acid, DHA was kinetically six times less reactive, although the EPA was by 16% more reactive.
Akimoto
Masamichi
M
Department of Applied Chemistry and Biotechnology, Niigata Institute of Technology, 1719 Fujihashi, Kashiwazaki, Niigata 945-1195, Japan. akimoto@acb.niit.ac.jp
Izawa
Maki
M
Hoshino
Kazumi
K
Abe
Ken-Ichi
K
Takahashi
Hiromi
H
D000818:Animals; D002384:Catalysis; D004042:Dietary Fats, Unsaturated / Q000138:chemical synthesis; D004281:Docosahexaenoic Acids / Q000737:chemistry*; D015118:Eicosapentaenoic Acid; D004800:Enzymes, Immobilized; D004951:Esterification; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D005395:Fish Oils / Q000138:chemical synthesis / Q000737:chemistry; D005399:Fishes; D008049:Lipase / Q000737:chemistry*; D008956:Models, Chemical; D012680:Sensitivity and Specificity; D013024:Soybean Oil / Q000138:chemical synthesis* / Q000737:chemistry
D004042:Dietary Fats, Unsaturated; D004800:Enzymes, Immobilized; D005231:Fatty Acids, Unsaturated; D005395:Fish Oils; D004281:Docosahexaenoic Acids; D013024:Soybean Oil; D015118:Eicosapentaenoic Acid; C093666:Lipozyme; D008049:Lipase