• Journal of the Korean Society of Food Science and Nutrition
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• v.38 no.8
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• pp.1062-1068
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• 2009

Diacylglycerol (DAG) were synthesized by enzymatic esterification of glyceryl monooleate (GMO) and conjugated linoleic acid (CLA) in a shaking water bath. The reaction was catalyzed by Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosa). Effects of reaction time, molar ratio, enzyme road and molecular sieves were studied. Results of normal-phase high performance liquid chromatography (NP-HPLC) analysis were performed. At 1:1, 2:1 and 3:1 (GMO : CLA) molar ratio and Lipozyme TLIM of 20% amount, DAG were produced in 42.6, 54.4 and 54.6 area% in 1 hr, respectively. When different Lipozyme TLIM amounts (2, 5, 10, 20%) were used with 2:1 (GMO : CLA) molar ratio, DAG were produced 21.4 (24 hr), 51.7 (12 hr), 56.2 (6 hr) and 54.4 (1 hr) area%, respectively. The reaction in the absence of molecular sieves increased DAG contents. The maximum DAG concentration conditions were obtained with molar ratio of 2:1 (GMO : CLA), lipase concentration of 10% (of substrate), 10% molecular sieves and reaction time of 6 hours at 55$^{\circ}C$. Under this reaction condition, produced DAG-rich oil was composed of 69 area% DAG, 7.9 area% TAG, 2 area% FFA, and 21.1 area% MAG.

• Journal of the Korean Society of Food Science and Nutrition
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• v.39 no.10
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• pp.1487-1494
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• 2010

Structured lipid (SL) for cocoa butter alternative was synthesized by interesterification of coconut oil fraction and palm stearin (6:4 and 8:2, by weight) in a shaking water bath at $60^{\circ}C$ and 180 rpm. It was performed for various reaction times (1, 2, 3, and 6 hr). The reaction was catalyzed by sn-1,3 specific Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosus). SL-solid part was obtained from acetone fractionation at $0^{\circ}C$. SL-solid part was blended with other palm oils and fractions for desirable property of cocoa butter alternative (SL-solid part : palm middle fraction : palm stearin solid : palm oil, 70.4:18.4:2.9:8.3, by weight). In reversed-phase HPLC analysis, triacylglycerol species of cocoa butter alternative had partition number of 40 (10.77%), 42 (13.06%), 44~46 (17.38%) and 48 (51.88%). Major fatty acids of cocoa butter alternative were lauric acid (16.5%), myristic acid (12.28%), palmitic acid (46.03%), and linoleic acid (14.75%). Solid fat content (SFC) and polymorphic form (${\beta}'$ form) of cocoa butter alternative prepared were similar to those of commercial cocoa butter replacer (CBR).

• Journal of the Korean Society of Food Science and Nutrition
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• v.33 no.5
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• pp.803-809
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• 2004

Monoacylglycerol (MG) and diacylglycerol (DG), as the components of enzymatically synthesized functional oil, were produced by glycerolysis of rice bran oil and glycerol using IM60 (immobilized lipase) in a stirredbatch reactor at 6$0^{\circ}C$ for 72 hours. After glycerolysis, the contents of triacylglycerol (TG), DG and MG in the produced functional oil were 41.71%,46.19%, and 11.15%, respectively. The functional oil also contained Phytosterols (2.04$\pm$0.17 mg/g), ${\gamma}$ -oryzanol (1.06$\pm$0.04 mg/g) and $\alpha$ -tocopherol (0.13$\pm$0.04 mg/g). In animal experiment the dietary effects of functional oil on hepatic acyl-CoA:cholesterol acyltransferase (ACAT) activities of the high cholesterol and high fat (HCHF)-fed mice were investigated. In functional oil-fed group, the liver ACAT activity was significantly lowered than in HCHF and corn oil-fed groups (p < 0.05). This results suggested that the synthesized functional oil may have an atheroproteetive effect by inhibiting ACAT activity.

• KSBB Journal
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• v.19 no.5
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• pp.385-389
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• 2004

In this research, the chemo-enzymatic synthesis of sorbitan methacrylate was investigated to optimize reaction conditions. Firstly, sorbitan was manufactured by sorbitol cyclic reaction in the presence of p-toluenesulfonic acid (p-TSA) as catalyst material. Secondly, sorbitan methacrylate was synthesized by immobilized lipase Novozyme 435 with acyl donors in t-butanol. As a result of enzymatic synthesis of sorbitan methacrylate, the conversion yield reached about $65\%$ in the condition of initial sorbitan conc. 50 g/L, enzyme content $3\%$ (w/v) , molar ratio 1:3, reaction temperature 50^{circ}C and reaction time 42 hrs using methyl methacrylate as acyl donor. Comparing with acyl donors and reaction temperature, the conversion yield reached about 18, 65 and $80\%$ with methacrylic acid, methyl methacrylate and vinyl methacrylate as acyl donor, respectively. And optimum reaction temperature was 60, 50, and 50^{circ}C, respectively

• Korean Journal of Agricultural Science
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• v.40 no.4
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• pp.367-375
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• 2013

The enzymatic interesterification was performed to produce structured lipids (SLs) with palm mid fraction (PMF) and stearic ethyl ester (STEE) for 1, 3, 6, 9, 12 and 15 hr at $80^{\circ}C$. The reaction was catalyzed by Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosus, amount of 20% by weight of total substrates) in a shaking water bath set at 180 rpm. The optimum condition for synthesis of asymmetric SLs were: substrate molar ratio 1:0.5 (PMF:STEE, by weight), reaction time 6 hr, enzyme 20% (wt%, water activity=0.085) of total substrate and reaction temperature $80^{\circ}C$. After reaction at optimized condition, triacylglycerols (symmetrical and asymmetrical TAGs) from reactants were isolated. POP/PPO (1,3-palmitoyl-2-oleoyl glycerol or 1,2-palmitoyl-3-oleoyl glycerol), POS/PSO (palmitoyl-oleoyl-stearoyl glycerol or palmitoyl-stearoyl-oleoyl glycerol), SOS/SSO (1,3-stearoyl-2-oleoyl glycerol or 1,2-stearoyl-3-oleoyl glycerol) were obtained by solvent fractionation. Finally, refined SLs contained stearic acid of 16.91%. Solid fat index and thermogram of the refined SLs were obtained using differential scanning calorimetry. The degree of asymmetric triacylglycerol in the refined SLs was analyzed by Ag-HPLC equipped with evaporated light scattering detector (ELSD). The refined SLs consisted of symmetric TAG of 41.15 area% and asymmetric TAG of 58.85 area%.

• Korean Journal of Food Science and Technology
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• v.36 no.4
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• pp.531-536
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• 2004

Synthesis conditions were optimized using response surface methodology for producing structured lipids (SL) by interesterification of DHA-enriched algae oil derived from microalgae, Schizochytrium sp. and corn oil. Reaction was performed fer 24 hr at $55^{\circ}C$ catalyzed by immobilized lipase from Rhizomucor miehei (RM IM) in shaking water bath. Major fatty acids of SL were palmitic (21.70 mol%), oleic (20.20 mol%), and linoleic (27.34 mol%) acids, and DHA (15.06 mol%). To separate newly synthesized SL-triglycerides (TG) species, HPLC with evaporative light scatting detector (ELSD) was used. Production conditions were optimized using central composite design with reaction temperature $(35-75^{\circ}C,\;X_1)$, reaction time $(2-42\;hr,\;X_2)$, and enzyme concentration $(2-14%,\;X_3)$ as variables. When variables were $70.28^{\circ}C\;(X_1),\;28.74\;hr\;(X_2),\;and\;11.30%\;(X_3)$, maximum content of selected three peaks of synthesized SL-TG species was predicted as 6.97 area%.

• Food Science and Preservation
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• v.16 no.2
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• pp.246-252
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• 2009

Diacylglycerol(DAG) was produced by enzymatic esterification of glyceryl mono-oleate(GMO) and conjugated linoleic acid(CLA) in a stirred-batch type reactor. The reaction was catalyzed by lipozyme RMIM(an immobilized lipase from Rizomucor miehei). DAG was isolated by a short-path distillation process and decolorized. DAG oil was composed of 87.3% DAG, 11.4% triacylglycerol(TAG), and 1.5% monoacylglycerol(MAG)(all w/w). Major fatty acids in DAG oil were oleic acid(54%), CLA(31.1%), and linoleic acid(7%). DAG oil iodine,and acid values were 108.8, 2.57, and 1, respectively. The DAG oil solid fat index(SFI) and thermograms were obtained using differential scanning calorimetry.

• Journal of the Korean Society of Food Science and Nutrition
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• v.39 no.8
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• pp.1156-1164
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• 2010

Structured lipids (SLs) were synthesized by enzymatic interesterification with evening primrose oil (EPO) and rice bran oil (RBO) in a batch-type reactor. The interesterification was performed using a water shaker for 24 hr at $55^{\circ}C$. Mixing speed was set at 200 rpm and Lipozyme RM IM (immobilized lipase from Rhizomucor miehei, 10% by weight of total substrates) was used as a biocatalyst. Rice bran oil and evening primrose oil were interesterified with various molar ratios (RBO : EPO, 1:3, 1:4, and 1:5 mol/mol). Reversed-phase high performance liquid chromatography connected with evaporative light-scattering detector was performed to separate the triacylglycerol (TAG) species of SLs. In the fatty acid analysis, $\gamma$-linolenic acid (7.9 mol%), linoleic acid (67.3 mol%) and oleic acid (13.2 mol%) were the most abundant fatty acids in the SLs. During 24 hr reaction, most of the reaction occurred within 3 hr. TAG compositions, tocopherols and phytosterols were also analyzed. In the TAG species analysis, LLL (ECN=42, L=linoleic acid) dramatically decreased when the reaction time increased.

• KSBB Journal
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• v.18 no.3
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• pp.222-228
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• 2003

This study was performed to research a chemo-enzymatic synthesis of sorbitan acrylate. It w as firstly to determine the optimum conditions for D-sorbitol cyclic reaction in the presence of p-toluenesulfonic acid (p-TSA) as catalyst material. It was secondly to find the optimum conditions for sorbitan acrylate synthesis using immobilized lipase Novozym 435 in t-butanol from its materials. The maximum yield of 1,4-sorbitan synthesis were obtained approximately 90% (w/w) at 13$0^{\circ}C$ and 200 mmHg vacuum pressure with 1% (w/w) p-TSA after 150 min reactin time on our experimental system. The product from optimum condition was less color than those obtained at higher temperatures and minimized byproduct and unreacted D-sorbitol. Sorbitan acrylate was synthesized to around 63.5% conversion of 1,4-sorbitan. The experimental optimum condition was found at 5$0^{\circ}C$, atmospheric pressure, 3% (w/v) Novozym 435, 50 g/L 1,4-sorbitan of initial reactant concentration, and 1:3 molar ratio of 1,4-sorbitan to acrylic acid.

• Food Science and Preservation
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• v.15 no.3
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• pp.437-444
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• 2008

Structured lipids(SLs) were synthesized by enzymatic interesterification with DHA-enriched fish oil(containing 27% docosahexaenoic acid) and soybean oil in the hatch-type reactor. The interesterification was performed for 24 hr at $55^{\circ}C$ and TLIM(immobilized lipase from Thermonyces lanuginosa, 10% by weight of total substrates) was mixed with 180 rpm of shaking. The fish oil and soybean oil were interesterifed with several weight ratio(fish oil : soybean oil, 2:8, 3:7, 4:6, 5:5, w:w), Reverse-phase high performance liquid chromatography with an evaporative light-scattering detector separated the triglyceride species of SLs. The products contained the newly synthesized peaks. Especially, one of peaks was distinctively increased with the increasing weight ratio from 2:8 to 5:5 while the peak of trilinolein (LLL) decreased vice versa. The effect of antioxidants such as catechin, BHT(Butylated hydroxytoluene), and their combinations on the oxidative stability in SL were investigated. Oxidative stability was carried out under oven test at $60^{\circ}C$ over 72 hr thereafter SLs were analyzed for total fatty acid content, rancimat, peroxide value, electronic nose and TBARS value. Among all combinations of antioxidant, the highest stability was obtained from 200 ppm of catechin. Besides, total tocopherol ($\alpha$, $\gamma$, and $\delta$-tocopherol), iodine and saponification value were analyzed in which iodine and saponification value of SLs were 151.19 and 182.35.