• Title/Summary/Keyword: interesterification

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A Study of the Enzymatic Interesterification Reaction for Producing Palmitoyl-Oleoyl-Stearoyl Triacylglycerol from the Palm Mid Fraction (팜중부유를 이용한 대칭형 Palmitoyl-Oleoyl-Stearoyl Triacylglycerol의 효소적 합성 반응 연구)

  • Lee, Seon-Mo;Shin, Jung-Ah;Hong, Soon-Tack;Lee, Ki-Teak
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.40 no.8
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    • pp.1113-1120
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    • 2011
  • Enzymatic interesterification was conducted with the palm mid fraction (PMF) and stearic ethyl ester for 1, 5, and 9 hr at 46$^{\circ}C$. The reaction was catalyzed by Lipozyme TLIM (2, 3, and 4% by weight of total substrates) in a shaking water bath at 180 rpm. As the reaction continued, oleic acid (C18:1) content at the sn-2 position decreased, whereas saturated fatty acid (C16:0 and C18:0) content increased. In the high performance chromatography analysis, 1,3-dipalmitoyl-2-oleoyl glycerol content decreased, whereas 1(3)-palmitoyl-2-oleoyl-3(1)-stearoyl glycerol (POS) content increased up to the reaction equilibrium. The rate of acyl migration increased with increasing molar ratio and enzyme load as well as reaction time. The optimal reaction conditions for maximizing POS content (53.5 area%) and minimizing acyl migration (23.1 area%) were obtained with a PMF : stearic ethyl ester=1:2 (molar ratio), Lipozyme TLIM 3 wt%, and a reaction time of 5 hr.

Synthesis of Diacylglycerol-Enriched Functional Lipid Containing DHA by Lipase-Catalyzed in Solvent-Free System (비 용매계에서 DHA가 함유된 Diacylglycerol의 효소적 반응에 의한 합성연구)

  • Kim, Nam-Sook;Lee, Ki-Teak
    • Korean Journal of Food Science and Technology
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    • v.37 no.4
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    • pp.584-589
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    • 2005
  • Structured triacylglycerol (SL-TAG) was synthesized by enzymatic interesterification with algae oil and soybean oil in solvent-free system. Structured di- and monoacylglycerol (SL-DAG/MAG) were produced by glycerolysis with SL-TAG and glycerol catalyzed by lipase. Reactions were performed by sn-1.3 specific Lipozyme RM IM lipase from Rhizomucor miehei (interesterification, 11%; glycerolysis 5% by weight of total substrates) in solvent-free system using stirred-batch type reactor. SL-DAG/MAG contained TAG (42,3 area%), 1,3-DAG (19.2 area%), 1,2-DAG (22.2 area%), MAG (16.0 area%), and free fatty acid (0.2 area%). Iodine and saponification values of SL-DAG/MAG were 208.8 and 179.6, respectively. SL-DAG/MAG appeared yellowish in color.

Enzymatic Synthesis of Low Trans Fats Using Rice Bran Oil, Palm Stearin and High Oleic Sunflower Seed Oil (미강유, 팜스테아린 및 고올레인산 해바라기씨유를 이용한 저트랜스 유지의 효소적 합성)

  • Kim, Ji-Young;Lee, Ki-Teak
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.38 no.4
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    • pp.470-478
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    • 2009
  • Low trans fats were synthesized by interesterification of rice bran oil (RBO), palm stearin (PS) and high oleic sunflower seed oil (HO) using TLIM from Thermomyces lanuginosa. After 24-h reaction, physicochemical characteristics such as fatty acid and triacylglycerol composition, solid fat content, melting point, tocopherol, oryzanol and phytosterol contents were evaluated. Trans fatty acid contents of the produced low-trans fats showed less than 0.5 wt%. Mostly, triacylglycerol species in the products were palmitoyl-linoleoyl-oleoyl-glycerol (PLO), palmitoyl-oleoyl-oleoyl-glycerol (POO) and palmitoyl-oleoyl-palmitoyl-glycerol (POP). Total tocopherol contents ranged from 6.94 to 11.83 mg/100 g while $0.18{\sim}0.49$ mg/100 g of $\gamma$-oryzanol and $182.47{\sim}269.08$ mg/100 g of phytosterols were observed depending on the substrates ratios. When the content of PS in the reaction substrate was increased, solid fat content and slip melting points were increased.

Elimination of Saturated Fatty Acids, Toxic Cyclic nonapeptide and Cyanogen Glycoside Components from Flax Seed Oil

  • Choi, Eun-Mi;Kim, Jeung-Won;Pyo, Mi-Kyung;Jo, Sung-Jun;Han, Byung-Hoon
    • Biomolecules & Therapeutics
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    • v.15 no.1
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    • pp.65-72
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    • 2007
  • Flax seed(Linseed, Linum usitatissimum L.) and its oil, a richest source of alpha-linolenic acid(ALA)(${\omega}-3$), contain saturated fatty acids, neurotoxic cyanogen glycosides and immuno-suppressive cyclic-nonapeptides. Present paper describes the development of two chemical processes, Process-A and -B, to remove saturated fatty acids and to destroy cyclic nonapeptides and cyanogen glycosides from flax seed oil. Process-A consists of three major steps, i.e., extraction of fatty acid mixture by alkaline saponification, removal of saturated fatty acid by urea-complexation, and triglyceride reconstruction of unsaturated fatty acid via fatty acyl-chloride activation using oxalyl chloride. Process-B consists of preparation of fatty acid ethyl ester by transesterification, elimination of saturated fatty acid ester by urea-complexation, and reconstruction of triglyceride by interesterification with glycerol-triacetate (triacetin). The destruction of lipophilic cyclic nonapeptide during saponification or transesterification processes could be demonstrated indirectly by the disappearance of antibacterial activity of bacitracin, an analogous cyclic-decapeptide. The cyanogen glycosides were found only in the dregs after hexane extraction, but not in the flax seed oil. The reconstructed triglyceride of flax seed oil, obtained by these two different pathways after elimination of saturated fatty acid and toxic components, showed agreeable properties as edible oil in terms of taste, acid value, iodine and peroxide value, glycerine content, and antioxidant activity.

Enzymatic synthesis of asymmetric structured lipids containing 1,2-disaturated-3-unsaturated glycerol using acyl migration (효소적 Acyl migration을 이용한 비대칭형 재구성지질(1,2-disaturated-3-unsaturated glycerol)의 합성 및 분석)

  • Hyeon, Jin-Woo;Lee, Ki-Teak
    • 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%.

Enzymatic reaction model for the production of symmetrical lipid molecules using the response surface methodology

  • Hong, Joon-Sun;Shin, Jung-Ah;Lee, Ki-Teak
    • Korean Journal of Agricultural Science
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    • v.45 no.2
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    • pp.265-282
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    • 2018
  • The purpose of this research was to produce symmetric (Saturated-Unsaturated-Saturated, SUS) triacylglycerol (TAG) using palm stearin fraction oil (PSFO) and high oleic sunflower oil (HOSO) as substrates to replace cocoa butter. PSFO was blended with HOSO (1 : 2 weight ratio), and $lipozyme^{(R)}$ TLIM (20 weight % of the substrate) was added. Interesterification was carried out in a shaking water bath at $55^{\circ}C$ at 220 rpm for 6 hours. The response surface methodology (RSM) through the central composite face design was employed to observe the optimized SUS-TAG. The independent factors were the reaction temperature ($X_1$: 65, 75 and $85^{\circ}C$), reaction time ($X_2$: 1, 3 and 5 hours) and ratio of TLIM ($X_3$: 10, 15 and 20 weight %). The dependent variables were $Y_1$ = Saturated-Unsaturated-Unsaturated (SUU, area %), $Y_2=SUS$ (area %), $Y_3$ = Saturated-Saturated-Unsaturated (SSU, area %), $Y_4$ = Unsaturated-Unsaturated-Unsaturated (UUU, area %), and $Y_5=sn-2$ unsaturated fatty acid (area %). The optimal conditions from the central composite face design minimized acyl migration while maximizing the presence of unsaturated fatty acid at the sn-2 position (73.43 area %). The optimal conditions were $X_1=65^{\circ}C$, $X_2=1hour$, and $X_3=20weight%$. As a result of the response surface analysis, the lack of fits was found as $Y_1=0.622$, $Y_2=0.438$, $Y_3=0.264$, $Y_4=0.526$, and $Y_5=0.215$, and their $R^2$ were 0.897, 0.944, 0.826, 0.857, and 0.867, respectively.

Detection and Determination of Lipase Activity

  • Lee, Seoung-Yong;Rhee, Joon-Shick
    • Journal of Microbiology and Biotechnology
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    • v.4 no.2
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    • pp.85-94
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    • 1994
  • Lipase (triacylglycerol hydrolase, EC 3.1.1.3) is able to catalyze the hydrolysis of ester bonds of triacylglycerols at the interface between aqueous phase and organic phase containing substrate. With the rapid development of lipid biotechnology, lipase-catalyzed hydrolysis of lipids has a great concern from the industrial point of view. Owing to the reversible nature of the lipase, the reactions are also applied for glyceride synthesis, interesterification and resolution of racemic mixtures into optically active alcohols or acids. For all applications of the lipases, a reliable method for the determination of enzyme activity is required. Precise quantitative determination of its activity is essential as the basis of research and development of the bioprocess involving the enzyme. This article reviews the existing literature on the detection and determination of lipase activity from microbial, mammalian and plant sources.

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Characterization of palm oil and its utilization in food industry (팜기름의 특성 및 식품산업에의 이용)

  • Yoon, Suk Hoo
    • Food Science and Industry
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    • v.50 no.3
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    • pp.70-92
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    • 2017
  • Crude palm oil (CPO) is obtained from the fruit of oil palm tree, and is rich in palmitic acid, ${\beta}$-carotene and vitamin E. CPO containing a balanced range of saturated and unsaturated fatty acids is fractionated mainly into liquid palm olein and solid palm. Palm oil is highly stable during frying due to its fatty acid composition, and the synergistic antioxidant activity of ${\beta}$-carotene and tocotrienol. Blending and interesterification of palm oil and other oils are the main processes used to offer functional, nutritional, and technical advantages to produce oils suitable for margarine, shortening, vanaspati, and frying oils etc. The advantages of using palm oil products include cheap raw materials, good availability, and low cost of processing, since hydrogenation is not necessary. Future research should lead to the production of oils with a higher oleic acid content and a higher content of vitamins E, carotenoids, and tocotrienols.

Characterization of Scaled-up Low-Trans Shortening from Rice Bran Oil and High Oleic Sunflower Seed Oil with Batch Type Reactor (회분식반응기를 이용한 미강유, 팜스테아린과 고올레인산 해바라기씨유 유래 대량 제조된 저트랜스 쇼트닝의 특성 연구)

  • Kim, Ji-Young;Lee, Ki-Teak
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.38 no.3
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    • pp.338-345
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    • 2009
  • Scaled-up low-trans shortening (LTS) was produced by lipase-catalyzed interesterification. Blend of rice bran oil (RBO), palm stearin (PS) and high oleic sunflower seed oil (HO) with 1:2:0.9 (w/w/w) ratio was interesterified using immobilized lipase from Thermomyces lanuginosus (TLIM) in the batch type reactor at $65^{\circ}C$ for 24 hr, and physicochemical melting properties of LTS were compared with commercial shortening. Solid fat content (SFC) of commercial shortening (used as control) and LTS was similar at 9.56 and 8.77%, respectively, at $35^{\circ}C$. Major fatty acids in LTS were C16:1 (33.7 wt%), C18:1 (45.7 wt%) and C18:2 (13.4 wt%). Trans fatty acid content in the commercial shortening (4.8 wt%) was higher than that of LTS (0.5 wt%). After reverse-phase HPLC analysis, major triacylglycerol (TAG) species in LTS were POO, POP and PLO. Total tocopherol, ${\gamma}$-oryzanol and phytosterol contents in the LTS were 12.37, 0.43 and 251.38 mg/100 g, respectively. Hardness of LTS was similar to that of commercial shortening. Also, x-ray diffraction analysis showed coexistence of ${\beta}'$ and ${\beta}$ form in the LTS.

Enzymatic Interesterification and Melting Characteristic for Asymmetric 1,2-Distearoyl-3-Oleoyl-rac-Glycerol Triacylglycerol Enriched Product (효소적 반응을 이용한 비대칭형 1,2-Distearoyl-3-Oleoyl-rac-Glycerol 혼합물의 생성 및 융점 특성)

  • Kim, Jin Young;Lee, Ki Teak
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.43 no.1
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    • pp.93-101
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    • 2014
  • Asymmetric 1,2-distearoyl-3-oleoyl-rac-glycerol (SSO) triacylglycerol (TAG) is used as a cocoa butter replacer (CBR). In this study, it was produced by lipase-catalyzed interesterification of fully hydrogenated soybean oil (FHSBO) and oleic ethyl ester (OEE) in a batch type reactor at $75^{\circ}C$, 250 rpm. Different molar ratios (FHSBO : OEE=1:1, 1:2 and 1:3, w/w) and various reaction times (1, 2, 3, 4, and 5 hr) were also tested. The optimized condition for SSO was a FHSBO : OEE molar ratio of =1:1 at reaction times of 2, 3, 4, and 5 hr. Enzymatic synthesis generated SSO/SOS, as well as the other TAGs (e.g., PSO/POS, SOO/OSO, SSS), ethyl esters, monoacylglycerol (MAG), and diacylglycerol (DAG). After scale-up, fractionation by solvent (methanol and acetone) fractionation and column chromatography was applied. To reduce ethyl esters, high-melting TAGs (e.g., SSS), and SOO/OSO in reactants, solvent fractionation was applied. Using a silica gel column (sample : silica gel=2:1, wt%), MAG and DAG were removed at $25^{\circ}C$. The major fatty acid composition of the final products (with a high SSO/SOS content) was palmitic acid (C16:0, 10.9~12.9 area%), stearic acid (C18:0, 52.2~54.9 area%), and oleic acid (C18:1, 34.2~35.5 area%). In reversed-phase HPLC analysis, the major TAG species of the final product (FHSBO : OEE=1:1, 2 hr) were SSO/SOS (82.31 area%) and PSO/POS (14.51 area%). Based on the $[SS]^+$ : $[SO]^+$ ratio obtained by RP-HPLC/APCI-MS, the final product had a higher SSO (AAB type TAG) content than cocoa butter (CB). The solid fat index (SFI) of CB and the final product obtained were similar with a narrow melting point range around ~32 to $35^{\circ}C$.