Comparison of antioxidant activities of selected phenolic compounds in O/W emulsions and bulk oil.

Antioxidant activities of 1-o-galloylglycerol (GG), propyl gallate, rosmarinic acid (RA), tocopherols (TOC), and 1:1 combinations of GG/RA and GG/TOC were evaluated using in vitro assays including 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS+), and ferric reducing antioxidant power (FRAP). Soybean oil stripped of TOC was utilized as bulk oil and as the oil phase in O/W emulsions for accelerated oxidation test with the selected phenolic compounds. Efficacies of antioxidants were evaluated by monitoring total oxidation (TOTOX) values and fatty acid profiles of oil and O/W samples during the accelerated oxidation. In bulk oil, GG outperformed other singular antioxidants, preventing 39.04% of oxidation for ω-3 fatty acids with a TOTOX value of 166.68. In emulsions, TOC outperformed other singular antioxidants, preventing 38.04% of oxidation with a TOTOX value of 196.72. Considering the polarities of the antioxidants and our testing systems, these results provide supporting evidence for the polar paradox theory.

Modification of palm-based oil blend via interesterification: Physicochemical properties, crystallization behaviors and oxidative stabilities.

Interesterification is widely employed as an effective technique to modify oils and fats. This study utilizes palm-based oil (palm olein: palm kernel oil: palm stearin, 5:3:2, w/w/w) as the raw material for the interesterification process performed in a pilot-scale packed bed reactor. Enzymatic interesterification (EIE) was catalyzed by Lipozyme TL IM (813.0 g) at 60℃ with reaction flow rate of 100 mL/min. Chemical interesterification (CIE) was catalyzed using sodium methoxide (0.3 wt%) as catalyst at 105 °C for 30 min. The results showed that the EIE fats had lower solid fat content tendency compared to that of CIE fats. The crystallization onset temperature was higher in EIE fats (23.09℃) compared to that of CIE (19.08℃). The results were consistent with the crystallization kinetics whereby the Avrami K constants of EIE fats were higher than that of CIE fats at various temperatures, indicating rapid crystallization and instant nucleation. Linear growth mechanism was dominant and the crystals formed were smaller in size as observed using polarized light microscope. The interesterified fats exhibited the presence of ß and ß'-crystals. While most of the tocopherol content was retained after EIE (386.18 ug/g), the molecular distillation process reduced the tocopherol concentration (110.01 ug/g) which consequently affected the oxidative stability. The findings in this work contribute to the fundamental understanding on the differences between CIE and EIE fats and provides data to support the preparation of modified fats via EIE that shows great potential as a controllable technique for industrialization.

Oxidative stability of cod liver oil in the presence of herring roe phospholipids.

The aim of this research was to investigate the effect of herring roe phospholipids (PLs) on the oxidative stability of cod liver oil during storage. The effect of PLs on the oxidative stability of cod liver oil was assessed in terms of peroxide value, free fatty acids, secondary oxidation products and pyrrolisation. The results show that the PV was lower in cod liver oil containing PLs (P < 0.05) than in the control without PLs. Benzaldehyde, 2,5-dimethylpyrazine, 2-methyl-2-pentenal, 1-penten-3-ol and 3-methylbutanal were the main volatiles. In addition, significant pyrrolisation was observed after 28 days when PLs were added to cod liver oil. The results suggested that cod liver oil with dispersed PLs was oxidized during storage followed by non-enzymatic browning reactions. The findings indicated that the ratio between pyrroles formed and α-tocopherol may influence the formation of new peroxides and secondary oxidation products.

Effect of Oil Type and Emulsifier on Oil Absorption of Steam-and-fried Instant Noodles.

The effects of four different frying oils and three emulsifiers on oil absorption by steam-and-fried instant noodles were evaluated. The blended oil (high oleic sunflower oil/soybean oil/palm oil = 24:25:1 (v/v/v)) containing approximately 50% oleic acid was chosen as the proper frying oil due to lower oil absorption by instant noodle compared to palm, soybean, and high oleic sunflower oils. Among the four oils, the interfacial tension between high oleic sunflower oil and instant noodle was the lowest (0.073 mN/m), resulting in the highest oil uptake (15.47%), while the lowest interfacial tension (0.30 mN/m) between blended oil and instant noodle resulted in the lowest oil uptake by the fried product (12.63%). Scanning electron microscopy (SEM) and confocal laser scanning microscopy (CLSM) were used to observe surface properties and oil distribution. The instant noodle fried in blended oil was found to have uniform oil distribution and smooth surface. After selecting the proper frying oil, three emulsifiers (soybean lecithin, Tween-80, Span-80, at 0.2% (v/v)) were added to the blended frying oil. Adding emulsifier into frying oil significantly decreased the interfacial tension between frying oil and instant noodle. Among the three emulsifiers, addition of soybean lecithin resulted in the lowest interfacial tension (0.010 mN/m) and the highest oil uptake (18.36%). Therefore, from this study, we do not recommend adding emulsifier into frying oil.

Mango kernel fat fractions as potential healthy food ingredients: A review.

Mango kernel fat (MKF) has been reported to have high functional and nutritional potential. However, its application in food industry has not been fully explored or developed. In this review, the chemical compositions, physical properties and potential health benefits of MKF are described. MKF is a unique fat consisting of 28.9-65.0% of 1,3-distearoyl-2-oleoyl-glycerol with excellent oxidative stability index (58.8-85.2 h at 110 °C), making the fat and its fractions suitable for use as high-value added food ingredients such as cocoa butter alternatives, trans-free shortenings, and a source of natural antioxidants (e.g., sterol, tocopherol and squalene). Unfortunately, the long period of dehydration of mango kernels at hot temperature results in the hydrolysis of triacylglycerols. The high levels of hydrolysates (mainly free fatty acids and diacylglycerols) limit the application of MKF in manufacturing these food ingredients. It is suggested that the physico-chemical and functional properties of MKF could be further improved through moderated refining (e.g., degumming and physical deacidification), fractionation, and interesterification.

Lipase - catalyzed Modification of Rice Bran Oil Solid Fat Fraction.

This study used a rice bran oil solid fat fraction (RBOSF) to produce cocoa butter alternatives via interesterification reaction catalyzed by immobilized lipase (Lipozyme® RM IM) in hexane. Effects of reaction time (6, 12, and 18 h), temperature (55, 60, and 65°C), mole ratios of 3 substrates [RBOSF:palm olein:C18:0 donors (1:1:2, 1:2:3, and 1:2:6)] were determined. The substrate system was dissolved in 3 mL of hexane and 10% of lipase was added. Two sources of C18:0 donors, stearic acid (SAd) and ethyl stearate (ESd) were used. Pancreatic lipase - catalyzed sn-2 positional analysis was also performed on both substrates and structured lipids (interesterification products). Structured lipids (SL) were analyzed by gas - liquid chromatography (G40.35LC) for fatty acid composition. Major fatty acids of RBOSF were C18:1, oleic acid (OA, 41.15±0.01%), C18:2, linoleic acid (LA, 30.05±0.01%) and C16:0, palmitic acid (PA, 22.64±0.01%), respectively. A commercial raw cocoa butter (CB) contained C18:0, stearic acid (SA, 33.13±0.04%), OA (32.52±0.03%), and PA (28.90±0.01%), respectively. Fatty acids at sn-2 position of RBOSF were OA (46.52±0.63%) and LA (42.98±1.1%), while major fatty acid at sn-2 position of CB was OA (85.24±1.22%). The RBOSF had low SA (2.40±0.01%) compared to CB (33.13±0.04%). The content of OA (46.52±0.63%) at sn-2 position in RBOSF was half of that found in CB (85.24±1.22%). Optimal reaction was 1:2:6 mole ratio of the substrate (RBOSF:PO:SAd), at 65°C for 12 h. Fatty acid compositions of the SL were 31.72±0.99% SA, 30.91±0.53% LA, 23.18±0.32% OA, and 13.26±0.34% PA, respectively. Fatty acids at sn-2 position of the SL were 53.72±4.21% OA, 25.11±3.69% LA, 14.18±1.58% PA, and 6.99±0.02% SA, respectively. DSC curves showed the melting point of CB at 20.94°C, while those of the SL were 14.15 and 40.35°C, respectively. The melting completion temperature (Tmc) of CB was 25.5°C while that of SL was 43.9°C, respectively.

The impact of lactation and gestational age on the composition of branched-chain fatty acids in human breast milk.

Breast milk consumption reduces the incidence of necrotizing enterocolitis (NEC) in preterm infants compared to formula. Branched-chain fatty acids (BCFAs) are present in breast milk but not in most formulas intended for preterm infants. We aimed to determine the composition of BCFAs in the breast milk of mothers with preterm infants, and to understand the impact of gestational age at birth and stage of lactation on BCFA content. The main BCFAs in preterm breast milk were iso-14:0, iso-15:0, anteiso-15:0, iso-16:0, iso-17:0, and anteiso-17:0. Breast milk BCFAs as a percent of total fatty acids (g per 100 g, %) were significantly different across lactation stages, with the highest concentration in colostrum, followed by transitional and mature breast milk (median: 0.41, 0.31, and 0.28%, respectively, p < 0.05). Lower BCFAs in preterm breast milk compared to term breast milk may have been related to maternal intake, or the ability of the mammary gland to extract BCFA from plasma, or differences in mammary gland BCFA synthesis. BCFAs were mainly in the sn-2 position (52-65%), similar to palmitic acid. Overall, preterm and term breast milk BCFAs were similar and showed specific concentration patterns, resembling 16:0 with respect to sn-2 positional distribution. BCFAs were reduced with lactation stage, similar to highly unsaturated fatty acids.

A Nuclear Magnetic Resonance Spectroscopy Approach to Discriminate the Geographic Origin of Roasted Asian Sesame Oils.

The aim of this study was to discriminate the geographic origin of Korean, Chinese, and Indian sesame oils distributed in Korea using 1H NMR spectroscopy in combination with canonical discriminant analysis (CDA). 1H NMR spectra were obtained from 84 roasted oil samples prepared from 51 Korean, 19 Chinese, and 14 Indian sesame seeds. The integration values of 26 peaks observed in the NMR spectra were determined and normalized on the basis of the peak derived from the terminal CH3 of the fatty acids (0.7446-1.0445 ppm). The variables selected for the CDA include the integration value of one peak (2.7208-2.8533 ppm) that signifies the CH2 between two C=C bonds from linoleic acid and the integration values of three peaks (2.9811-3.1151 ppm, 3.5914-3.6819 ppm, and 5.9471-5.9625 ppm) attributed to the protons of sesamolin. The CDA results showed that 80 of the 84 oil samples and five of the six additional commercial sesame oil samples were correctly classified based on their production site. This study demonstrated that 1H NMR spectroscopy is a useful tool to simultaneously analyze the relative abundance of linoleic acid and sesamolin in the sesame oils and good discrimination between the three Asian sesame oils could be achieved when the 1H NMR analytical data were used in combination with CDA.

Infant Formula Fat Analogs and Human Milk Fat: New Focus on Infant Developmental Needs.

Human breast milk is generally and universally recognized as the optimal choice for nutrition during the first year of life. In certain cases in which it is not feasible to breast-feed the infant or the breast milk is not sufficient, especially in the case of preterm infants, infant formula is the next best alternative to provide nutrition to nurture the infant. Therefore, it is highly important that the nutrient composition of the infant formula is as close to breast milk as possible for proper growth and development of the infant. However, human milk is a complex dynamic matrix, and therefore significant research has been done and is still ongoing to fully understand and mimic human breast milk, particularly its fat composition. Lipids play a critical role in infant nutrition. A number of advances have been made in infant formula lipid content and composition so that formula can better simulate or mimic the nutritional functions of human maternal milk.

Microencapsulation of stearidonic acid soybean oil in Maillard reaction-modified complex coacervates.

The antioxidant capacity of Maillard reaction (MR)-modified gelatin (GE)-gum arabic (GA) coacervates was optimized to produce microcapsules with superior oxidative stability compared to the unmodified control. MR was used to crosslink GE and GA, with or without maltodextrin (MD), to produce anti-oxidative Maillard reaction products (MRP) which was used to encapsulate stearidonic acid soybean oil (SDASO) by complex coacervation. Biopolymer blends (GE-GA [1:1, w/w] or GE-GA-MD [2:2:1, w/w/w]) were crosslinked by dry-heating at 80°C for 4, 8, or 16h. Relationships between the extent of browning, Trolox equivalent antioxidant capacity (TEAC), and the total oxidation (TOTOX) of encapsulated SDASO were fitted to quadratic models. The [GE-GA-MD] blends exhibited higher browning rates and TEAC values than corresponding [GE-GA] blends. Depending on the type of biopolymer blend and dry-heating time, TOTOX values of SDASO in MRP-derived microcapsules were 29-87% lower than that of the non-crosslinked control after 30 days of storage.

Antioxidant activities of annatto and palm tocotrienol-rich fractions in fish oil and structured lipid-based infant formula emulsion.

The abilities of annatto and palm tocotrienol-rich fractions (TRFs), as natural antioxidants, to inhibit lipid oxidation in menhaden fish oil and structured lipid-based infant formula emulsion, were evaluated and compared. The peroxide and anisidine values of the bulk oil and oil-in-water emulsion samples stored at 37°C were measured over a 28-day period. The results showed that annatto TRF was a more effective antioxidant than palm TRF and α-tocopherol in both food systems at 0.02% and 0.05%. Factors, including structural differences in chromanol head and isoprenoid tail, polarity, concentration, oxidation time, and the method used to monitor lipid oxidation, were responsible for the different behaviours of tocopherols and tocotrienols. In contrast to the reported findings in vivo, addition of α-tocopherol (0-75%) did not interfere with the antioxidant activity of tocopherol-free annatto TRF in foods. Our findings may lead to the development of new natural antioxidant products for food applications.

Enzymatic synthesis of extra virgin olive oil based infant formula fat analogues containing ARA and DHA: one-stage and two-stage syntheses.

Structured lipids (SLs) with high palmitic acid content at the sn-2 position enriched with arachidonic acid (ARA) and docosahexaenoic acid (DHA) were produced using extra virgin olive oil, tripalmitin, ARA and DHA single cell oil free fatty acids. Four types of SLs were synthesized using immobilized lipases, Novozym 435 and Lipozyme TL IM, based on one-stage (one-pot) and two-stage (sequential) syntheses. The SLs were characterized for fatty acid profile, triacylglycerol (TAG) molecular species, melting and crystallization profiles, tocopherols, and phenolic compounds. All the SLs had >50 mol % palmitic acid at the sn-2 position. The predominant TAGs in all SLs were PPO and OPO. The total tocopherol content of SL1-1, SL1-2, SL2-1, and SL2-2 were 70.46, 68.79, 79.64, and 79.31 µg/g, respectively. SL1-2 had the highest melting completion (42.0 °C) and crystallization onset (27.6 °C) temperatures. All the SLs produced in this study may be suitable as infant formula fat analogues.

Characterisation and optimisation of physical and oxidative stability of structured lipid-based infant formula emulsion: effects of emulsifiers and biopolymer thickeners.

Response surface methodology (RSM) was applied to investigate the effects of lecithin (0-0.4 g/100 ml), monoacylglycerol (0-0.4 g/100 ml), locust bean gum (LBG; 0-0.1 g/100 ml), and carrageenan (0-0.02 g/100 ml) on the physical and oxidative properties of structured lipid-based infant formula emulsion containing dairy proteins, lactose, vitamins, minerals and other micronutrients. Particle size, optical stability, viscosity, relative content of docosahexaenoic acid, stearidonic acid and total oxidation value were assessed during 28-day storage. ANOVA results showed that the experimental data were satisfactorily fitted to second-order polynomial models by multiple linear regression. The contour plots illustrated that lecithin and monoacylglycerol played a dominant role in controlling the emulsion stability compared to LBG and carrageenan. Lecithin content significantly affected all the responses measured, particularly lipid oxidation. Increasing monoacylglycerol concentration led to an increase in particle size and emulsion viscosity. The optimal condition to achieve the highest stability was predicted to be 0.2, 0.4, 0.045, and 0.015 g/100 ml lecithin, monoacylglycerol, LBG and carrageenan, respectively. The verification data further demonstrated the suitability of the models explored by RSM. Overall, the findings obtained in this study have important implications for the successful incorporation of structured lipid into infant formula emulsion for better infant nutrition and health.

Identification and quantification of phytochemical composition and anti-inflammatory, cellular antioxidant, and radical scavenging activities of 12 Plantago species.

Twenty-eight seed samples of 12 Plantago species were investigated for their chemical compositions and anti-inflammatory, cellular antioxidant, and radical scavenging properties. A new UPLC-UV procedure was developed and applied to quantify acteoside and geniposidic acid, the characteristic constituents of the genus Plantago. The amounts of acteoside and geniposidic acid ranged from 0.07 to 15.96 mg/g and from 0.05 to 10.04 mg/g in the tested samples, respectively. Furthermore, 26 compounds were tentatively identified by UPLC/Q-TOF-MS analysis. The Plantago samples significantly differed in their phytochemical compositions. The extracts of Plantago seeds also showed inhibitory effects on LPS-induced IL-1ß, IL-6, and COX-2 mRNA expression in RAW 264.7 mouse macrophage cells. Additionally, significant variations were observed among different samples on cellular antioxidant activities in HepG2 cells, as well as DPPH and hydroxyl radical scavenging capacities. The results from this study may be used to promote the use of the genus Plantago in improving human health.

Preparative separation of triterpene alcohol ferulates from rice bran oil using a high performance counter-current chromatography.

A novel method for the separation of two major triterpene alcohol ferulates from rice bran oil (RBO) was developed using a high performance counter-current chromatography (HPCCC). A two-phase solvent system of n-hexane-acetonitrile (1:1, v/v) was applied to purify cycloartenyl ferulate (CAF) and 24-methylene cycloartanyl ferulate (24-mCAF) from RBO. The yields were 20.50±2.60 mg CAF and 12.62±1.15 mg 24-mCAF from 390 mg RBO through a two-step separation procedure. The purities of the two compounds were 97.97±0.90% and 95.50±0.75%, respectively, as determined by high performance liquid chromatography (HPLC). Their chemical structures were confirmed by ultra performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS), and (1)H, (13)C and 2D nuclear magnetic resonance (NMR). This represents the first report on direct separation of CAF and 24-mCAF from RBO by HPCCC.

Production of trans-free margarine with stearidonic acid soybean and high-stearate soybean oils-based structured lipid.

UNLABELLED: Omega-3 fatty acids (n-3 FAs) have been positively associated with prevention and treatment of chronic diseases. Intake of high amounts of trans fatty acids (TFAs) is correlated with increased risk of coronary heart disease, inflammation, and cancer. Structured lipid (SL) was synthesized using stearidonic acid (SDA) soybean oil and high-stearate soybean oil catalyzed by Lipozyme(®) TLIM lipase. The SL was compared to extracted fat (EF) from a commercial brand for FA profile, sn-2 positional FAs, triacylglycerol (TAG) profile, polymorphism, thermal behavior, oxidative stability, and solid fat content (SFC). Both SL and EF had similar saturated FA (about 31 mol%) and unsaturated FA (about 68 mol%), but SL had a much lower n-6/n-3 ratio (1.1) than EF (5.8). SL had 10.5 mol% SDA. After short-path distillation, a loss of 53.9% was observed in the total tocopherol content of SL. The tocopherols were lost as free tocopherols. SL and EF had similar melting profile, ß' polymorph, and oxidative stability. Margarine was formulated using SL (SLM) and EF (RCM, reformulated commercial margarine). No sensory difference was observed between the 2 margarines. The SL synthesized in this study contained no TFA and possessed desirable polymorphism, thermal properties, and SFC for formulation of soft margarine. The margarine produced with this SL was trans-free and SDA-enriched. PRACTICAL APPLICATION: The current research increases the food applications of stearidonic acid (SDA) soybean oil. trans-Free SDA containing SL was synthesized with desirable polymorph, thermal properties, and SFC for formulation of soft margarine. The margarine produced with this SL had no trans fat and had a low n-6/n-3 ratio. This may help in reducing trans fat intake in our diet while increasing n-3 FA intake.

Production of human milk fat analogue containing docosahexaenoic and arachidonic acids.

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-, ß-, 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.

Conclusions and recommendations from the symposium, Heart Healthy Omega-3s for Food: Stearidonic Acid (SDA) as a Sustainable Choice.

Faculty who had presented at the symposium "Heart Healthy Omega-3s (n-3 fatty acids) for Food: Stearidonic Acid (SDA) as a Sustainable Choice" met and agreed upon conclusions and recommendations that could be made on the basis of evidence provided at the symposium. The participants also submitted manuscripts relating to their topics and these are presented in this supplement. These manuscripts were reviewed and also contributed to the conclusions and recommendations presented herein. The three major objectives of the symposium were to: 1) increase understanding of the current and emerging knowledge regarding the health benefits of (n-3) fatty acids (FA) including a focus on stearidonic acid (SDA) and EPA; 2) evaluate the importance of increasing (n-3) FA consumption in the US and the current challenge of doing so via mainstream foods; and 3) consider the health and food application benefits of SDA as a precursor to EPA and a plant-based sustainable source of highly unsaturated (n-3) FA for mainstream foods. Specific areas for future research were defined and included in the summary and conclusions herein. Overall evidence-based conclusions included: the current evidence provides a strong rationale for increasing (n-3) FA intakes in the US and other populations; current consumption of (n-3) FA in most populations is either insufficient or not efficient at providing adequate tissue levels of the long-chain (n-3) FA EPA and DHA; SDA in soybean oil appears to be a cost-effective and sustainable plant-based source that could contribute to reaching recommended levels of (n-3) FA intake, but more research and surveillance is needed; and adding SDA-enriched soybean oil to foods should be considered as a natural fortification approach to improving (n-3) FA status in the US and other populations. References for these conclusions and recommendations can be found in the articles included in the supplement.

Incorporation of (n-3) fatty acids in foods: challenges and opportunities.

The health benefits of long-chain (n-3) PUFA have been widely reported in the literature. Despite the potential benefits, consumption of these fatty acids continues to fall below recommendations from various health and regulatory agencies. Incorporation of long-chain PUFA in foods represents a considerable challenge due to the increased risk of lipid oxidation resulting in the development of off-flavors and reduced shelf life. As a result, new sources of (n-3) fatty acids are needed that are more efficiently converted to long-chain (n-3) fatty acids than α-linolenic acid (ALA) and can be more easily incorporated into food. Stearidonic acid [SDA, 18:4 (n-3)] is an intermediate in the desaturation of ALA to EPA. Soybeans have been modified to contain SDA. Clinical studies have demonstrated a significant increase in EPA levels when SDA is consumed. Being more stable, SDA has been added to a variety of foods and has demonstrated equal consumer acceptance compared to a regular soybean oil control. SDA-enhanced soybean oil can provide to food companies and consumers an option to increase (n-3) fatty acid consumption in foods consumers typically eat.

Modifications of stearidonic acid soybean oil by enzymatic acidolysis for the production of human milk fat analogues.

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.