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1.
Incorporation of stearic acid into canola oil to produce trans-free structured lipid (SL) as a healthy alternative to partially hydrogenated fats for margarine formulation was investigated. Response surface methodology was used to study the effects of lipozyme RM IM from Rhizomucor miehei and Candida rugosa lipase isoform 1 (LIP1) and two acyl donors, stearic acid and ethyl stearate, on the incorporation. Lipozyme RM IM and ethyl stearate gave the best result. Gram quantities of SLs were synthesized using lipozyme RM IM, and the products were compared to SL made by chemical catalysis and fat from commercial margarines. After short-path distillation, the products were characterized by GC and RPHPLC-MS to obtain fatty acid and triacylglycerol profiles, 13C NMR spectrometry for regiospecific analysis, X-ray diffraction for crystal forms, and DSC for melting profile. Stearic acid was incorporated into canola oil, mainly at the sn-1,3 positions, for the lipase reaction, and no new trans fatty acids formed. Most SL products did not have adequate solid fat content or beta' crystal forms for tub margarine, although these may be suitable for light margarine formulation.  相似文献   

2.
Stearic acid was enzymatically transesterified with high-laurate canola using a nonspecific lipase from Candida antarctica to produce structured lipids (SL) suitable for margarine application. Stearic acid levels ranged from 10 to 40 wt % of high-laurate canola oil. Differential scanning calorimetry was used to evaluate melting characteristics of the transesterified products. A stearic acid level of 30% was found to best match the melting characteristics of fat extracted from commercially available stick margarine. This SL was used to prepare nonrefrigerated and refrigerated margarine samples. Refrigerated margarine was prepared using 60% SL and 40% canola oil, whereas 100% SL was used for the nonrefrigerated margarine. Slip melting point, solid fat content, and hardness index were determined for all samples. Application of a dynamic temperature step using a dynamic stress rheometer showed complete breakdown of the commercial stick margarine and the experimental refrigerated margarine at approximately 30 degrees C and complete breakdown of the nonrefrigerated margarine at approximately 35 degrees C. Addition of canola oil to the SL improved spreadability at refrigeration temperatures and reduced the hardening effect of lauric acid in the SL. The nonrefrigerated margarine was spreadable at room temperature and exhibited no oil exudation or phase separation.  相似文献   

3.
Stearidonic acid soybean oil (SDASO) is a plant source of n-3 polyunsaturated fatty acids (n-3 PUFAs). Solvent-free enzymatic interesterification was used to produce structured lipids (SLs) in a 1 L stir-batch reactor with a 1:2 substrate mole ratio of SDASO to tripalmitin, at 65 °C for 18 h. Two SLs were synthesized using immobilized lipases, Novozym 435 and Lipozyme TL IM. Free fatty acids (FFAs) were removed by short-path distillation. SLs were characterized by analyzing FFA and FA (total and positional) contents, iodine and saponification values, melting and crystallization profiles, tocopherols, and oxidative stability. The SLs contained 8.15 and 8.38% total stearidonic acid and 60.84 and 60.63% palmitic acid at the sn-2 position for Novozym 435 SL and Lipozyme TL IM SL, respectively. The SLs were less oxidatively stable than SDASO due to a decrease in tocopherol content after purification of the SLs. The saponification values of the SLs were slightly higher than that of the SDASO. The melting profiles of the SLs were similar, but crystallization profiles differed. The triacylglycerol (TAG) molecular species of the SLs were similar to each other, with tripalmitin being the major TAG. SDASO's major TAG species comprised stearidonic and oleic acids or stearidonic, α-linolenic, and γ-linolenic acids.  相似文献   

4.
Production in a batch reactor with a solvent-free system of structured triacylglycerols containing short-chain fatty acids by Lipozyme RM IM-catalyzed acidolysis between rapeseed oil and caproic acid was optimized using response surface methodology (RSM). Reaction time (t(r)), substrate ratio (S(r)), enzyme load (E(l), based on substrate), water content (W(c), based on enzyme), and reaction temperature (T(e)), the five most important parameters for the reaction, were chosen for the optimization. The range of each parameter was selected as follows: t(r) = 5-17 h; E(l) = 6-14 wt %; T(e) = 45-65 degrees C; S(r) = 2-6 mol/mol; and W(c) = 2-12 wt %. The biocatalyst was Lipozyme RM IM, in which Rhizomucor miehei lipase is immobilized on a resin. The incorporation of caproic acid into rapeseed oil was the main monitoring response. In addition, the contents of mono-incorporated structured triacylglycerols and di-incorporated structured triacylglycerols were also evaluated. The optimal reaction conditions for the incorporation of caproic acid and the content of di-incorporated structured triacylglycerols were as follows: t(r) = 17 h; S(r) = 5; E(l) = 14 wt %; W(c) = 10 wt %; T(e) = 65 degrees C. At these conditions, products with 55 mol % incorporation of caproic acid and 55 mol % di-incorporated structured triacylglycerols were obtained.  相似文献   

5.
Structured triacylglycerols (ST) from canola oil were produced by enzymatic acidolysis in a packed bed bioreactor. A commercially immobilized 1,3-specific lipase, Lipozyme IM, from Rhizomucormiehei, was the biocatalyst and caprylic acid the acyl donor. Parameters such as substrate flow rate, substrate molar ratio, reaction temperature, and substrate water content were examined. High-performance liquid chromatography was used to monitor the reaction and product yields. The study showed that all of the parameters had effects on the yields of the expected di-incorporated (dicaprylic) ST products. Flow rates below 1 mL/min led to reaction equilibrium, and lower flow rates did not raise the incorporation of caprylic acid and the product yield. Incorporation of caprylic acid and the targeted di-incorporated ST was increased by approximately 20% with temperature increase from 40 to 70 degrees C. Increasing the substrate molar ratio from 1:1 to 7:1 increased the incorporation of caprylic acid and the product yield slightly. Water content in the substrate also had a mild influence on the reaction. Water content at 0.08% added to the substrate gave the lowest incorporation and product yield. The use of solvent in the medium was also studied, and results demonstrated that it did not increase the reaction rate at 55 degrees C when 33% hexane (v/v) was added. The main fatty acids at the sn-2 position of the ST were C(18:1), 54. 7 mol %; C(18:2), 30.7 mol %; and C(18:3), 11.0 mol %.  相似文献   

6.
Structured lipids (SLs) containing palmitic, oleic, stearic, and linoleic acids, resembling human milk fat (HMF), were synthesized by enzymatic acidolysis reactions between tripalmitin, hazelnut oil fatty acids, and stearic acid. Commercially immobilized sn-1,3-specific lipase, Lipozyme RM IM, obtained from Rhizomucor miehei was used as the biocatalyst for the enzymatic acidolysis reactions. The effects of substrate molar ratio, reaction temperature, and reaction time on the incorporation of stearic and oleic acids were investigated. The acidolysis reactions were performed by incubating 1:1.5:0.5, 1:3:0.75, 1:6:1, 1:9:1.25, and 1:12:1.5 substrate molar ratios of tripalmitin/hazelnut oil fatty acids/stearic acid in 3 mL of n-hexane at 55, 60, and 65 degrees C using 10% (total weight of substrates) of Lipozyme RM IM for 3, 6, 12, and 24 h. The fatty acid composition of reaction products was analyzed by gas-liquid chromatography (GLC). The fatty acids at the sn-2 position were identified after pancreatic lipase hydrolysis and GLC analysis. The results showed that the highest C18:1 incorporation (47.1%) and highest C18:1/C16:0 ratio were obtained at 65 degrees C and 24 h of incubation with the highest substrate molar ratio of 1:12:1.5. The highest incorporation of stearic acid was achieved at a 1:3:0.75 substrate molar ratio at 60 degrees C and 24 h. For both oleic and stearic acids, the incorporation level increased with reaction time. The SLs produced in this study have potential use in infant formulas.  相似文献   

7.
Interesterified plastic fats were produced with trans-free substrates of fully hydrogenated soybean oil, extra virgin olive oil, and palm stearin in a weight ratio of 10:20:70, 10:40:50, and 10:50:40, respectively, by lipase catalysis. The major fatty acids of the products were palmitic (32.2-47.4%), stearic (12.0-12.4%), and oleic acid (33.6-49.5%). After storage at 5 degrees C (refrigerator temperature) or 24 degrees C (room temperature) for 16 h, the physical properties were evaluated for solid fat content, texture, melting, and crystallization behavior, viscoelastic properties, crystal polymorphism, and crystal microstructure. The interesterified fats contained desirable crystal polymorphs (beta' form) as determined by X-ray diffraction spectroscopy. They exhibited a wide plastic range of solid fat content of 52-58% at 10 degrees C and 15% at 40 degrees C. The physical properties were influenced by the ratio of palm stearin and olive oil. Harder and more brittle texture, crystallization and melting at higher temperature, higher solid fat contents, and more elastic (G') or viscous (G') characteristics were observed in the produced fats containing a higher content of palm stearin and lower content of olive oil. The produced fats stored at 5 degrees C consisted mostly of beta' form crystal together with a small content of beta form, while those at 24 degrees C had only beta' form. The produced fat with a higher amount of palm stearin appeared to have more beta' form crystal and small size crystal clusters. Thus, the physical properties of the produced plastic fats may be desirable for use in a bakery product.  相似文献   

8.
The optimization of solid fat content (SFC) and crystal properties of trans-free structured lipids (SL) synthesized by incorporating stearic acid into canola oil was investigated. The SLs were blended with varying amounts of palm midfraction (PMF). The SFC and crystal polymorphism were improved. The addition of sucrose stearate (S-170), sorbitan tristearate (STS), and distilled monoglycerides (DMG) to one of the blends, SL40:PMF (70:30, w/w), did not improve crystal polymorphism but had significant effects on crystal morphology. The emulsifiers significantly delayed crystal growth, resulting in smaller crystal sizes as compared to the control. They were unable to inhibit the formation of granular crystals (30-140 microm), which are undesirable in margarine, after 4 weeks of storage at 0 degrees C. Blends treated with S-170 and STS showed many small evenly distributed crystals interspersed with large crystal aggregates (after 4 weeks of storage), whereas the blend treated with DMG and the control showed irregularly shaped globular crystals, also interspersed with large crystal aggregates. However, these crystal aggregates were not observed upon visual and physical examination and may therefore not impart the sensory properties of the finished products negatively.  相似文献   

9.
Tripalmitin-enriched triacylglycerols were concentrated from palm stearin by acetone fractionation and as the substrate reacted with a mixture of equimolar quantities of fatty acids (C8:0-C18:3). The incorporation degree and acyl migration level of the fatty acids and acylglycerols composition were investigated, providing helpful information for the production of human milk fat substitutes. Higher incorporation degrees of the fatty acids were obtained with lipase PS IM, Lipozyme TL IM, and Lipozyme RM IM followed by porcine pancreatic lipase and Novozym 435-catalyzed acidolysis. During reactions catalyzed by Lipozyme TL IM, Lipozyme RM IM, and lipase PS IM, incorporation degrees of C12:0, C14:0, C18:1, and C18:2 were higher than those of other fatty acids at operated variables (molar ratio, temperature, and time), and the triacylglycerols content reached the highest (82.09%) via Lipozyme RM IM-catalyzed acidolysis. On the basis of significantly different levels of acyl migration to the sn-2 position, lipases were in the order of lipase PS IM < Lipozyme TL IM < Lipozyme RM IM.  相似文献   

10.
trans-Free interesterified fat was produced for possible usage as a margarine. Palm stearin, coconut oil, and canola oil were used as substrates for chemical interesterification. The main aim of the present study was to evaluate the physicochemical properties of blends of palm stearin, coconut oil, and canola oil submitted to chemical interesterification using sodium methoxide as the catalyst. The original and interesterified blends were examined for fatty acid composition, softening and melting points, solid fat content, and consistency. Chemical interesterification reduced softening and melting points, consistency, and solid fat content. The interesterified fats showed desirable physicochemical properties for possible use as a margarine. Therefore, our result suggested that the interesterified fat without trans-fatty acids could be used as an alternative to partially hydrogenated fat.  相似文献   

11.
Structured lipids (SLs) containing palmitic and oleic acids were synthesized by transesterification of tripalmitin with either oleic acid or methyl oleate as acyl donor. This SL with palmitic acid at the sn-2 position and oleic acid at sn-1,3 positions is similar in structure to human milk fat triacylglycerol. LIP1, an isoform of Candida rugosa lipase (CRL), was used as biocatalyst. The effects of reaction temperature, substrate molar ratio, and time on incorporation of oleic acid were investigated. Reaction time and temperature were set at 6, 12, and 24 h, and 35, 45, and 55 degrees C, respectively. Substrate molar ratio was varied from 1:1 to 1:4. The highest incorporation of oleic acid (37.7%) was at 45 degrees C with methyl oleate as acyl donor. Oleic acid resulted in slightly lesser (26.3%) incorporation. Generally, higher percentage incorporation of oleic acid was observed with methyl oleate (transesterification) than with oleic acid (acidolysis). In both cases percentage incorporation increased with reaction time. Incorporation decreased with increase in temperature above 45 degrees C. Initially, oleic acid incorporation increased with increase in substrate molar ratio up to 1:3. LIP1 was also compared with Lipozyme RM IM as biocatalysts. The tested reaction parameters were selected on the basis of maximum incorporation of C18:1 obtained during optimization of LIP1 reaction conditions. Reaction temperature was maintained at 45, 55, and 65 degrees C. Lipozyme RM IM gave highest oleic acid incorporation (49.4%) at 65 degrees C with methyl oleate as acyl donor. Statistically significant (P < 0.05) differences were observed for both enzymes. SL prepared using Lipozyme RM IM may be more suitable for possible use in human milk fat substitutes.  相似文献   

12.
In this study enzymatic-interesterified margarine fats with different conversion degrees were produced in a packed-bed reactor. The effects of conversion degree on the formation of free fatty acids and diacyglycerols, solid fat content, crystallization behavior, microstructure, and crystal network were investigated, and the enzymatically interesterified products were compared with a chemically interesterified product. Formation of free fatty acids and diacyglycerols increased slightly with increasing conversion degree. The solid fat content was higher at 10 and 20 degrees C and lower at 30, 35, and 40 degrees C with increasing conversion degree. Increased conversion degree from the blend to products, measured by X-ray with addition of 50% of rapeseed oil for dilution, caused the content of beta to decrease from 100% to 33%, and 30% and eventually to pure beta' crystal. However, double chain packing was observed for both the blend and products. Isothermal crystallization kinetics was characterized by the Fisher-Turnbull model. The highest free energy was observed for the blend. A small deformation with oscillation tests shows a significant difference between the blend and interesterified products. The differences of microstructure between the blend, different conversion degree, and chemical randomized product were observed.  相似文献   

13.
Structured lipids (SLs) from stearidonic acid (SDA) soybean oil pre-enriched with palmitic acid (PA) at the sn-2 position with Novozym 435 (NSL) or Lipozyme TL IM (LSL) from previous research were further enriched with γ-linolenic acid (GLA) or docosahexaenoic acid (DHA). Small-scale acidolysis reactions with Lipozyme TL IM were performed to determine the optimal reaction conditions as 1:1 substrate mole ratio of NSL or LSL to free DHA at 65 °C for 24 h and a 1:0.5 substrate mole ratio of NSL or LSL to free GLA at 65 °C for 12 h. Optimized SL products were scaled up in a 1 L stir-batch reactor, and the resulting SLs of NSL:DHA (NDHA), LSL:DHA (LDHA), NSL:GLA (NGLA), and LSL:GLA (LGLA) were chemically and physically characterized. The SLs contained >54% PA at the sn-2 position with GLA >8% for the GLA SLs and DHA >10% for the DHA SLs. The oxidative stabilities of the SLs were increased by the addition of 200 ppm TBHQ, with NGLA being more stable due to higher tocopherol content than the other SLs. The melting and crystallization profiles did not differ between the DHA SLs or the GLA SLs. The triacylglycerol (TAG) species were similar for the GLA SLs but differed between the DHA SLs, with tripalmitin being the major TAG species in all SLs.  相似文献   

14.
Stearidonic acid (SDA, C18:4n-3) enriched soybean oil may be added to the diet to increase intake of omega-3 fatty acids (FAs). Human milk fat has ≥60% of palmitic acid (PA), by weight, esterified at the sn-2 position to improve absorption of fat and calcium in infants. Enzymatic interesterification of SDA soybean oil and tripalmitin produced structured lipids (SLs) enriched with PA at the sn-2 position of the triacylglycerol. Reactions were catalyzed by Novozym 435 or Lipozyme TL IM under various conditions of time, temperature, and substrate mole ratio. Response surface methodology was used to design the experiments. Model optimization conditions were predicted to be 1:2 substrate mole ratio at 50 °C for 18 h with 10% (by weight) Lipozyme TL IM resulting in 6.82 ± 1.87% total SDA and 67.19 ± 9.59% PA at sn-2; 1:2 substrate mole ratio at 50 °C for 15.6 h resulting in 8.01 ± 2.41% total SDA and 64.43 ± 13.69% PA at sn-2 with 10% (by weight) Novozym 435 as the biocatalyst. The SLs may be useful as human milk fat analogues for infant formula formulation with health benefits of the omega-3 FAs.  相似文献   

15.
Structured Lipid was synthesized from canola oil and caprylic acid with sn-1,3 specific lipase from Rhizomucor miehei. Cold spreadable butter was made by blending butterfat with the SL at a weight ratio of 80:20. Its chemical and physical properties were compared with pure butter and butterfat-canola oil 80:20 blend spread. The butterfat-SL blend had lower contents of hypercholesterolemic fatty acids (FAs) and the lowest atherogenic index (AI) as compared to the others. Melting and crystallization behaviors of butterfat-SL blend were similar to those of butterfat-canola oil blend above 0 degrees C. It showed solid fat contents (SFCs) similar to butterfat-canola oil blend but lower than pure butterfat. The butterfat-SL blend was shown to crystallize in the beta' form. There were no differences between the hardness of butterfat-SL blend spread and butterfat-canola oil blend spread. Rheological analysis showed that butterfat-SL blend spread lost its elastic behavior at 5 degrees C, a lower temperature than pure butter.  相似文献   

16.
Human milk fat (HMF) analogue containing docosahexaenoic acid (DHA) and arachidonic acid (ARA) at sn-1,3 positions and palmitic acid (PA) at sn-2 position was produced. Novozym 435 lipase was used to produce palmitic acid-enriched hazelnut oil (EHO). EHO was then used to produce the final structured lipid (SL) through interesterification reactions using Lipozyme RM IM. Reaction variables for 3 h reactions were temperature, substrate mole ratio, and ARASCO/DHASCO (A:D) ratio. After statistical analysis of DHA, ARA, total PA, and PA content at sn-2 position, a large-scale production was performed at 60 °C, 3:2 A:D ratio, and 1:0.1 substrate mole ratio. For the SL, those results were determined as 57.3 ± 0.4%, 2.7 ± 0.0%, 2.4 ± 0.1%, and 66.1 ± 2.2%, respectively. Tocopherol contents were 84, 19, 85, and 23 μg/g oil for α-, β-, γ-, and δ-tocopherol. Melting range of SL was narrower than that of EHO. Oxidative stability index (OSI) value of SL (0.80 h) was similar to that of EHO (0.88 h). This SL can be used in infant formulas to provide the benefits of ARA and DHA.  相似文献   

17.
A kind of low-calorie structured lipid (LCSL) was obtained by interesterification of tributyrin (TB) and methyl stearate (St-ME), catalyzed by a commercially immobilized 1,3-specific lipase, Lipozyme RM IM from Rhizomucor miehei . The condition optimization of the process was conducted by using response surface methodology (RSM). The optimal conditions for highest conversion of St-ME and lowest content LLL-TAG (SSS and SSP; S, stearic acid; P, palmitic acid) were determined to be a reaction time 6.52 h, a substrate molar ratio (St-ME:TB) of 1.77:1, and an enzyme amount of 10.34% at a reaction temperature of 65 °C; under these conditions, the actually measured conversion of St-ME and content of LLL-TAG were 78.47 and 4.89% respectively, in good agreement with predicted values. The target product under optimal conditions after short-range molecular distillation showed solid fat content (SFC) values similar to those of cocoa butter substitutes (CBS), cocoa butter equivalent (CBE), and cocoa butters (CB), indicating its application for inclusion with other fats as cocoa butter substitutes.  相似文献   

18.
Analysis of the biochemical composition of Irvingia malayana was carried out. This Cambodian nut contains 7.5% water and 70% oil. Most of the fatty acids are saturated and include 42% C12:0 and 41.8% C14:0; the sterol composition is similar to that of other vegetable oils. This oil is less rich in alpha-tocopherol than in gamma-tocopherol. Analysis of the solid content of the oil with respect to the temperature by NMR shows a fast fall of solid content around its fusion range at 38-39 degrees C. The main differences in the properties of the indigenous Cambodia nut from other known oleaginous seeds are in its selenium content, fatty acid composition, fusion temperature profile, and content of antioxidants. These important characteristics can soon make possible its application in pharmacology, cosmetics, the margarine industry, etc.  相似文献   

19.
Interesterification of a 60:40 (wt/wt) mixture of olive oil and fully hydrogenated canola oil was carried out in a batch reactor using a commercial immobilized lipase from Thermomyces lanuginose as a biocatalyst. The effects of a stepwise change of temperature on the degree of conversion, the solid fat content (SFC) of the products, and the residual activity of the enzyme were investigated. As a reference condition, an interesterification trial was conducted at a constant temperature of 70 degrees C for 48 h. For trials in which a temperature of 70 degrees C was used for the first 4 h of reaction and a temperature of 60 degrees C was employed for the following 44 h, there were no significant differences (p < 0.05) in the overall degree of conversion relative to the reference condition. Oils interesterified for only 1 or 2 h at 70 degrees C had melting points higher than 60 degrees C, whereas an oil produced by interesterification at 70 degrees C for only 4 h had a melting point of 58 degrees C. There was little difference (p < 0.05) between the SFC profiles of the interesterification products prepared by two different temperature protocols (70 degrees C for 24 h; 70 degrees C for 4 h followed by 60 degrees C for 20 h). Use of the protocol involving a step decrease in temperature significantly decreased catalyst deactivation effects, thereby increasing the residual activity of the immobilized lipase.  相似文献   

20.
The effect of dispersed aqueous droplets in water-in-oil (W/O)-emulsion semisolid fats on aroma release and sensory perception was investigated on margarine models where model aroma substances were added. Aroma release from W/O-emulsion fat blends and bulk fat blends with added monoglycerides combining different fatty acids of various short-chain free fatty acids, methylketones, esters, and lactones were measured using headspace solid phase microextraction-gas chromatography/mass spectrometry (SPME-GC/MS), and their perception profiles were evaluated by sensory analysis. The presence of aqueous phase in a fat blend significantly reduced the headspace concentrations of butanoic acid and hexanoic acid, and also decreased the perceived intensity of total aroma and cheesy aroma. The aroma release of methylketones, esters, and lactones from the W/O-emulsion fat blends increased with increasing carbon chain length of the volatile molecules. The intensity of aroma perception in a W/O-emulsion fat blend depended on the melting point of the fatty acids (oleic, palmitic, stearic, and behenic) of the monoglyceride used as an emulsifier. Thus, aroma release from a W/O-emulsion semisolid fat blend was influenced by interactions between aroma volatiles and the dispersed aqueous droplets and by their viscoelastic properties.  相似文献   

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