Antioxidant activity of phenolic compounds in sunflower oil‐in‐water emulsions containing sodium caseinate and lactose

The aim of this work was to study the evolution of oxidation and the efficiency of phenolic antioxidants in sunflower oil‐in‐water emulsions containing sodium caseinate and lactose (Cas‐Lac) or stabilized by Tween‐20 (T‐20). Two groups of phenolic antioxidants which are structurally similar were tested, i.e. (1) α‐tocopherol and its water‐soluble analogue, Trolox; and (2) gallic acid and its ester derivatives propyl gallate and dodecyl gallate. Emulsion samples were oxidized at 40 °C and the progress of oxidation was followed through quantitation of oxidized triacylglycerol monomers, dimers and oligomers. Results showed that Cas‐Lac emulsions were more stable to oxidation than T‐20 emulsions. In both types of emulsions, the most protective antioxidants were the compounds of lower polarity, namely, α‐tocopherol and dodecyl gallate. It was also found that substantial amounts of α‐tocopherol coexisted with significant polymerization, which was indicative of the heterogeneity of oxidation, i.e. differences of oxidation rate in oil droplets.     

Characterization of the effects of β‐carotene on the thermal oxidation of triacylglycerols using HPLC‐ESI‐MS

RP HPLC method coupled to ESI‐MS was used for the analysis and characterization of the oxidation of model triacylglycerols (TAGs) in presence of β‐carotene. β‐Carotene was added to the TAGs and oxidized in the Rancimat at 110°C. The samples were separated isocratically using a mixture of isopropanol with methanol and a Phenomenex C18 column. β‐Carotene degradation was measured using high performance TLC. We found that β‐carotene plays an important role during the thermal degradation of high oleic acid model TAGs. Half of the β‐carotene was degraded before 3 h of thermal treatment. β‐Carotene significantly increases the peroxide value of the TAGs after the third hour, suggesting a pro‐oxidant action. However, different TAGs show different activity toward thermal treatment and β‐carotene. The LLL was found to be less stable, OLL and OLO were stable till 10 and 12 h respectively, while POO, OOO, and OSO were the stable TAGs till 14 h. In TAGs, replacing linoleic acid by oleic acid, the stability of the corresponding TAG was found to increase by 2 h. A new class of oxidized TAGs was reported for the first time, together with previously reported species. The proposed mechanism of formation and identification of the newly identified species have been explained. Among the oxidized species of TAGs, mono‐hydroperoxides, bis‐hydroperoxides, epoxy‐epidioxides, and epoxides were the major compounds identified.     

Oxidation at elevated temperatures: competition between α‐tocopherol and unsaturated triacylglycerols

The competitive oxidation between α‐tocopherol and unsaturated fatty acyls at thermoxidation conditions (180 and 240 °C) was evaluated using purified triacylglycerols from nine fats and oils (refined coconut, palm, tallow, olive, high oleic sunflower, sunflower, corn, soybean, and flaxseed oil). α‐Tocopherol degraded faster in less unsaturated lipids and a linear correlation between the iodine value (x) and the residual tocopherol content (y) was obtained after 2 h of heating at 240 °C (y = 3.72x + 137.5, R² = 0.9463). The formation of polar oxidation products was established and the results were explained by a non‐selective oxidation of unsaturated fatty acyls and α‐tocopherol by highly reactive alkoxyl and hydroxyl radicals generated by decomposition of hydroperoxides.     

A polyphenol extract of tara pods (Caesalpinia spinosa) as a potential antioxidant in oils

Tara is a native species of Peru and is widely distributed in Latin America; its fruits (pods) have a high potential for medical, industrial and food uses. A supercritical tara polyphenol extract (STPE) was obtained from tara pods by supercritical fluid extraction (SFE) with CO₂. The antioxidant activity of the STPE was studied in two oils, regular and high‐oleic sunflower oil (SO, HOSO), with and without their natural antioxidants. Under accelerated conditions of oxidation, a linear relationship was observed in antioxidant‐stripped oils between the polyphenol content of the STPE and the induction period. The antioxidant effect of STPE on the HOSO was studied at 60°C. The highest polyphenol concentration of STPE showed the greatest α‐tocopherol degradation and the lowest hydroperoxide formation, which implies that α‐tocopherol causes the regeneration of the polyphenols that protect the TAGs in HOSO. Tara pods combined with SFE method could be used as a source of antioxidants in oils.     

Increasing gamma‐ and delta‐tocopherols in oils improves oxidative stability

Over the past two decades, plant geneticists have revolutionized how fatty acid compositions of vegetable oils are optimized to improve oxidative stability and functionality. Now, the expertise of plant geneticists is reaching beyond altering fatty acids to changing other oil components such as tocopherols. Basic lipid research on optimizing tocopherol profiles and ratios in vegetable oils is providing information for geneticists to breed the next generation of oxidatively stable vegetable oils. This review will discuss three studies; first, a basic study to determine the oxidative stability provided by the addition of pure gamma and delta tocopherols to oils treated to remove natural tocopherols; second, a practical study to evaluate the oxidative stability of mid‐oleic sunflower oil from seeds modified by plant breeding to contain high amounts of γ‐ and δ‐tocopherols; and third, a frying test to determine the effects of gamma tocopherol addition.     

Oxidative Stability and Changes in Chemical Composition of Extra Virgin Olive Oils After Short‐Term Deep‐Frying of French Fries

We aimed at investigating oxidative stability and changes in fatty acid and tocopherol composition of extra virgin olive oil (EVOO) in comparison with refined seed oils during short‐term deep‐frying of French fries, and changes in the composition of the French fries deep‐fried in EVOO. EVOO samples from Spain, Brazil, and Portugal, and refined seed oils of soybean and sunflower were studied. Oil samples were used for deep‐frying of French fries at 180 °C, for up to 75 min of successive frying. Tocopherol and fatty acid composition were determined in fresh and spent vegetable oils. Tocopherol, fatty acid, and volatile composition (by SPME–GC–MS) were also determined in French fries deep‐fried in EVOO. Oil oxidation was monitored by peroxide, acid, and p‐anisidine values, and by Rancimat after deep‐frying. Differential scanning calorimetry (DSC) analysis was used as a proxy of the quality of the spent oils. EVOOs presented the lowest degree of oleic and linoleic acids losses, low formation of free fatty acids and carbonyl compounds, and were highly stable after deep‐frying. In addition, oleic acid, tocopherols, and flavor compounds were transferred from EVOO into the French fries. In conclusion, EVOOs were more stable than refined seed oils during short‐term deep‐frying of French fries and also contributed to enhance the nutritional value, and possibly improve the flavor, of the fries prepared in EVOO.     

Stability of the lipid fraction of milk‐based infant formulas during storage

A study is made of the effects of storage (time and temperature) on the lipid fraction of four milk‐based adapted infant formulas with basically the same composition, though differing in the iron salt added (lactate or sulfate) and/or the vitamin E source (α‐tocopherol or α‐tocopherol acetate). Peroxide value, hydroperoxide C₁₈ percentage and thiobarbituric acid‐reactive substance (TBARS) content were used as indicators of lipid peroxidation. Fat contents remained stable throughout storage. Peroxide values increased from the first storage month and were affected by storage time, although they exhibited irregular behavior. Storage time and temperature affected hydroperoxide percentage, which was seen to be the earliest indicator of lipid oxidation, being measurable in newly manufactured formulas. TBARS values were only affected by storage time. No statistically significant differences were found among the four infant formulas for any of the lipid oxidation indicators.     

Emulsifier type,metal chelation and pH affect oxidative stability of n‐3‐enriched emulsions

Recent research has shown that the oxidative stability of oil‐in‐water emulsions is affected by the type of surfactant used as emulsifier. The aim of this study was to evaluate the effect of real food emulsifiers as well as metal chelation by EDTA and pH on the oxidative stability of a 10% n‐3‐enriched oil‐in‐water emulsion. The selected food emulsifiers were Tween 80, Citrem, sodium caseinate and lecithin. Lipid oxidation was evaluated by determination of peroxide values and secondary volatile oxidation products. Moreover, the zeta potential and the droplet sizes were determined. Tween resulted in the least oxidatively stable emulsions, followed by Citrem. When iron was present, caseinate‐stabilized emulsions oxidized slower than lecithin emulsions at pH 3, whereas the opposite was the case at pH 7. Oxidation generally progressed faster at pH 3 than at pH 7, irrespective of the addition of iron. EDTA generally reduced oxidation, as evaluated by volatiles formation in all emulsions, irrespective of pH and emulsifier type, except in the lecithin and caseinate emulsions where a pro‐oxidative effect was observed for some volatiles. The different effects of the emulsifier types could be related to their ability to chelate iron, scavenge free radicals, interfere with interactions between the lipid hydroperoxides and iron as well as to form a physical barrier around the oil droplets.     

Formation of oxidation compounds in sunflower and olive oils under oxidative stability index conditions

The objective of this work was to study the evolution of oxidation under oxidative stability index (OSI) conditions using the Rancimat apparatus. Sunflower oils with different degrees of unsaturation (conventional high‐linoleic sunflower oil, genetically modified high‐oleic sunflower oil, and a 1 : 1 mixture of both of them) and virgin olive oil were used. The sunflower oils were tested at 100 °C, while the olive oil was assayed at 100, 110 and 120 °C. Samples were analyzed at different time points and conductivity values, until the induction period (IP) was overpassed. A combination of adsorption and size‐exclusion chromatography was used for the quantification of oxidized triacylglycerol (TG) monomers, dimers and polymers. Additionally, peroxide values (PV) and ultraviolet absorption at 270 nm (K₂₇₀), as well as losses of tocopherols, were measured. The results showed that oxidized TG monomers were the only group of oxidation compounds that increased during the early oxidation stage. The end of the IP was marked by the initiation of polymerization after the exhaustion of tocopherols. In comparison with reported results obtained at room temperature, the main difference found was that the amounts of oxidation compounds at the end of the IP were much lower at OSI test temperatures. With the exception of the K₂₇₀ values, the results also showed that the IP endpoints provided by the OSI test were slightly higher than those obtained by quantification of oxidized TG monomers or by PV determination.     

Two approaches in preparation for cogeneration α‐tocopherol and biodiesel from cottonseed

A two‐step process and a direct alkaline transesterification process in preparation for cogeneration α‐tocopherol and biodiesel (fatty acid methyl esters, FAME) from cottonseeds were studied in this article. The effects of some factors on recovery of α‐tocopherol and conversion of cottonseed oil (triacylglycerols, TAGs) to biodiesel in the two processes were systematically studied by single factor experiments and orthogonal design method. In the two‐step process, α‐tocopherol and biodiesel were produced from extraction with two‐phase solvent followed by base‐catalysed transesterification. Approximately 95.5% TAGs was converted into biodiesel, and 1.008 mg/g (wet basis) α‐tocopherol was detected on the condition: 1:3 petroleum ether/methanol volume rate, 40°C extraction temperature; 7:1 methanol/cottonseed oil molar ratio, 1.1% KOH (w/v) concentration in methanol and 60°C esterification temperature. And in the direct alkaline transesterification reaction, 98.3% conversion of TAGs and 0.986 mg/g content of α‐tocopherol could be achieved at 60°C in 2 h. Both of the two processes were feasible from the economic point of view for further utilisation of cottonseed. © 2011 Canadian Society for Chemical Engineering     

Oxidative stability of sunflower oils differing in unsaturation degree during long-term storage at room temperature

The objective of this work was to study the evolution of oxidation in sunflower oils differing in unsaturation degree during long-term storage at room temperature. For this purpose, a combination of adsorption and size-exclusion chromatographies was used for quantification of oxidized triacylglycerol (TG) monomers, dimers, and polymers. Conventional sunflower oil, genetically modified high-oleic sunflower oil, and a 1∶1 mixture of the two were used. Results showed that oxidized TG monomers were the only group of oxidation compounds increasing during the early oxidation stage, and an excellent correlation was found between amounts of oxidized TG monomers and PV during the induction period, independently of the degree of oil unsaturation. Both the rate of formation and the amount of oxidized TG monomers accumulated at the end of the induction period increased as the unsaturation degree of the oils tested was higher. The end of the induction period was marked by the initiation of polymerization and exhaustion of tocopherol. Therefore, the concomitant determination of oxidized TG monomers and polymerization compounds provided a complete picture of the oxidation process.     

The effect of fatty acid composition of rapeseed oil on plasma lipids and oxidative stability of low‐density lipoproteins in cholesterol‐fed hamsters

We studied the effect of four rapeseed oils with different fatty acid profiles on parameters implicated in the pathogenesis of atherosclerosis in humans in a model experiment with hamsters. The hamsters were divided into seven groups and fed a semi‐synthetic, cholesterol‐enriched diet (5 g/kg diet) containing 15% of the fat in question for a period of six weeks. The following rapeseed oils were used: (1) conventional rapeseed oil (6% saturated fatty acids [SFA], 64% monounsaturated fatty acids [MUFA], 18% linoleic acid [LA], 9% α‐linolenic acid [ALA]), (2) linoleic acid‐rich rapeseed oil (6% SFA, 61% MUFA, 28% LA, 2% ALA), (3) oleic acid‐rich rapeseed oil (6% SFA, 74% MUFA, 11% LA, 5% ALA), (4) myristic acid‐rich rapeseed oil (11% myristic acid, 35% SFA, 44% MUFA, 14% LA, 5% ALA). Sunflower oil, olive oil and lard were used as control fats. The concentrations of the lipids in the plasma, in the lipoprotein fractions and in the liver, the fatty acid composition of various tissues, the tocopherol status and the susceptibility of low‐density lipoproteins (LDL) to in vitro‐oxidation were determined. The concentrations of total cholesterol found in the plasma and in the LDL fraction and the ratios of LDL to HDL were similar after feeding the four different types of rapeseed oil, sunflower oil and olive oil. Lard produced the highest concentrations of cholesterol in plasma and the LDL fraction and the highest ratio of LDL to HDL. Feeding conventional, oleic acid‐ and myristic acid‐rich rapeseed oils resulted in markedly lower ratios of arachidonic to eicosapentaenoic acid in the lipids of the liver and the erythrocytes. This is considered beneficial for the formation of eicosanoids. The lag‐time before the onset of peroxidation of the LDL lipids, induced by copper ions, was not statistically significant between the seven hamster groups suggesting that the susceptibility of LDL to lipid peroxidation was similar after feeding all types of fat. Considering all parameters obtained in the used hamster model it is obvious that all four rapeseed oils are at least as favourable as olive oil or sunflower oil.     

Kinetics of antioxidant action of α‐ and γ‐toco‐pherols in sunflower and soybean triacylglycerols

A kinetic analysis was performed to evaluate the antioxidant behavior of α‐ and γ‐to‐copherols (5—2000 ppm) in purified triacylglycerols obtained from sunflower oil (TGSO) and soybean oil (TGSBO) at 100 °C. Different kinetic parameters were determined, viz. the stabilization factor as a measure of effectiveness, the oxidation rate ratio as a measure of strength, and the antioxidant activity which combines the other two parameters. In the low concentration range (up to 400 ppm in TGSBO and up to 700 ppm in TGSO) α‐tocopherol was a more active antioxidant than γ‐tocopherol whereas the latter was more active at higher concentrations. It has been found that the different activity of the tocopherols is not due to their participation in chain initiation reactions, but that the loss of antioxidant activity at high tocopherol concentrations is due to their consumption in side reactions. The rates of these reactions are higher in TGSBO than in TGSO. Both α‐tocopherol itself and its radicals participated more readily in side reactions than γ‐tocopherol and its radicals. Both α‐ and γ‐tocopherol reduce lipid hydroperoxides, thus generating alkoxyl radicals which are able to amplify the rate of lipid oxidation by participating in chain propagation reactions.     

A non‐extractable condensed‐tannins fiber reduces thermal oxidation in oils at frying temperature

Several compounds presenting antioxidant properties have been tested in frying oils to delay thermal oxidation of the triglycerides containing unsaturated fatty acids. The present study was designed to evaluate, for the first time, the antioxidant and antipolymerizing effects of addition of Exxenterol®, a denatured carob fiber very rich in non‐extractable tannins, on olive oil (OO), sunflower oil (SO) and a homogeneous blend of both oils. Exxenterol was added to the three oils in amounts of 50, 250, 500 and 1000 mg/kg oil before heating. After 36 h of heating at 180 °C, there was a large and relevant increase of the polar material and the polymer contents, but tocopherol decreased to non‐detectable levels in all three oils. Polar content, polymer and thermal oxidation formation (p ≤0.004) and tocopherol degradation (p ≤0.022) were significantly and dose‐dependently inhibited by Exxenterol. Both polar material and polymer formation were inhibited (at least by 44%) in OO and SO and at least by 27% in the oil blend when 1000 mg/kg oil of this product was added. Small but detectable amounts of tocopherol were found in the oil blend containing 50 mg Exxenterol/kg. The results clearly show that this non‐extractable tannin‐rich fiber can be successfully employed as an additive to prolong oil shelf life at frying temperature.     

γ‐ and δ‐tocopherols are more effective than α‐tocopherol on the autoxidation of a 10% rapeseed oil triacylglycerol‐in‐water emulsion with and without a radical initiator

The antioxidative effects of γ‐ and mainly δ‐tocopherol in a multiphase system were hardly considered up to now. The aim of this study was i) to assess the effects and ii) to follow the degradation of α‐, γ‐ and δ‐tocopherol in concentrations of 0.01%, 0.05%, 0.1% and 0.25% during the oxidation of a 10% purified rapeseed oil triacylglycerol‐in‐water emulsion at 40 °C in the dark for 15 wk in a system containing a low oxygen concentration. Oxidation experiments were performed weekly by assessing the formation of hydroperoxides and hexanal, and the stability of the tocopherols was determined using high‐performance liquid chromatography. Storage tests were conducted with and without the addition of 0.01% α, α′‐azoisobutyronitrile (AIBN), which is a known radical initiator. α‐Tocopherol increased the formation of hydroperoxides in both tests as well as the generation of hexanal when the radical initiator was added; furthermore it was the least stable. γ‐Tocopherol delayed the formation of hexanal and prolonged the stability of the emulsion in a dose‐dependant manner. δ‐Tocopherol was the most stable and also the most effective in delaying lipid oxidation in the emulsions. Each concentration that was tested reduced the rate of hydroperoxide and especially hexanal formation. Hexanal was only formed to a slight extent after 15 wk of oxidation in the test with AIBN and the lowest dose of 0.01% δ‐tocopherol. For all tocopherols, strong correlations were found between tocopherol stability and the extent of oxidation. Results suggest that i) mainly δ‐tocopherol, but also γ‐tocopherol even less pronounced, are very good antioxidants in order to stabilize and prolong the shelf life of oil‐in‐water emulsions, ii) the antioxidative effects were intensified with increasing amounts.     

Antioxidant effect of mono‐ and dihydroxyphenols in sunflower oil with different levels of naturally present tocopherols

Antioxidant properties of mono‐ and dihydroxyphenolic acids and their alkyl esters were examined, with emphasis on the relationship between their molecular structure and antioxidant activity. Test media with different tocopherol level were used for determining the oxidative stability: original refined sunflower oil (total tocopherols 149.0 mg/kg), partially tocopherol‐stripped sunflower oil (total tocopherols 8.7 mg/kg) and distilled fatty acid methyl esters (FAME) as a tocopherol‐free medium. The chemical reaction of tocopherols with diazomethane tested for the purpose to eliminate their antioxidant activity failed due to the negligible degree of methylation of hydroxyl group in the tocopherol molecule. Caffeic acid and protocatechuic acid (3,4‐dihydroxyphenolic acids) and their alkyl esters were found to be more active antioxidants than monohydroxyphenolic acid (p‐hydroxybenzoic acid), 2,5‐dihydroxyphenolic acid (gentisic acid), 3‐methoxy‐4‐hydroxyphenolic acids (vanillic and ferulic acids) and their corresponding alkyl esters. Naturally present tocopherols in refined sunflower oil proved to have a synergistic effect on gentisic acid but not on its alkyl esters. In contrast, tocopherols showed an antagonistic effect on alkyl esters of caffeic acid, because their protection factors decreased with increasing level of tocopherols in the test medium. Moreover, the antioxidant activity of these alkyl esters decreased with increasing length of their alkyl chain in conformity with the polar paradox hypothesis. Practical applications: Tocopherols as naturally present antioxidants influence considerably the antioxidant activity of other antioxidants added to plant oils used as a test medium. Distilled fatty acid methyl esters prepared from refined sunflower oil may serve as an optimal tocopherol‐free test medium. Some alkyl esters of phenolic acids were evaluated to be applicable as natural more lipophilic antioxidants in comparison with phenolic acids.     

Thermostability of genetically modified sunflower oils differing in fatty acid and tocopherol compositions

The objective of the study was to investigate the performance at frying temperature of a new sunflower oil with high content of oleic and palmitic acid (HOHPSO) and containing γ‐tocopherol as the most abundant natural antioxidant. HOHPSO either containing α‐ or γ‐tocopherol (HOHPSO‐α and HOHPSO‐γ, respectively) were obtained from genetically modified sunflower seeds and refined under identical conditions. The oil stability against oxidation, as measured by Rancimat at 120 °C, was much higher for the oil containing γ‐tocopherol, suggesting the higher effectiveness of γ‐tocopherol as compared to α‐tocopherol to delay oxidation. Experiments at high temperature (180 °C) simulating the conditions applied in the frying process clearly demonstrated that, for the same periods of heating, the oil degradation and the loss of natural tocopherol were significantly lower for the oil containing γ‐tocopherol. Comparison of different genetically modified sunflower oils with different fatty acid compositions confirmed that oil degradation depended on the fatty acid composition, being higher at a higher degree of unsaturation. However, the loss of tocopherol for a similar level of oil degradation was higher as the degree of unsaturation decreased. Overall, the results showed that HOHPSO‐γ had a very high stability at frying temperatures and that mixtures of HOHPSO‐α and HOHPSO‐γ would be an excellent alternative to fulfill the frying performance required by the processors and the vitamin E content claimed by the consumers.     

Chemical Characterization of a High‐Oleic Soybean Oil

High‐oleic low‐linolenic acid soybean oil (HOLLSB, Plenish^®) is an emerging new oil with projections of rapid expansion in the USA. HOLLSB has important technological advantages, which are expected to drive a gradual replacement of commodity oils used in food applications such as soybean oil. A key technological advantage of HOLLSB is its relatively high oxidation stability. This oxidation stability is the result of a favorable fatty acid composition, high (76%) oleic acid, low linoleic (6.7%), and alpha‐linolenic (1.6%) acids, and high concentration of tocopherols (936 ppm) after refining, enriched with the gamma‐homolog (586 ppm). A detailed analysis of the fatty acid composition of this HOLLSB by gas chromatography–mass spectrometry allowed the identification and structural determination of 9‐cis‐heptadecenoic acid (or 17:1n‐8). To our knowledge, this is the first time 9‐cis‐heptadecenoic acid has been unequivocally reported in soybean oil. This unusual fatty acid component has the potential to be used as a single authenticity marker for the quantitative assessment of soybean oil. The Rancimat induction period (IP) of Plenish^® (16.1 hours) was higher than those of other commercially available high‐oleic oils, such as canola (13.4 hours), and Vistive^® Gold (10 hours), a different variety of soybean oil. Plenish^® showed the same IP as high‐oleic sunflower oil. Plenish^® shows a modest increase in oxidation stability with the external addition or relatively high concentrations of tocopherols. The characteristic high oxidative stability of Plenish^® may be further enhanced with the use of nontocopherol antioxidants.     

Effect of different antioxidants on lycopene degradation in oil‐in‐water emulsions

There is interest in incorporating lycopene into foods because it is a natural pigment and can also play a role in preventing disease. Therefore, the effect of the addition of various antioxidants in lycopene containing oil‐in‐water emulsions stabilized with Tween 20 at acidic pH was studied in order to determine protection systems against lycopene oxidation. In this model, EDTA showed pro‐oxidant activity while other chelators like citric acid and tripolyphosphate showed no effect. The free radical scavengers, propyl gallate (PG), gallic acid (GA), and α‐tocopherol all had the ability to decrease lycopene oxidation with α‐tocopherol being the most effective. The combination of 1 µM α‐tocopherol and 10 µM GA was more effective than the individual antioxidants. Addition of ascorbic acid to the combination of α‐tocopherol and GA system accelerated lycopene loss. These results suggest that by the proper selection of free radical scavenging antioxidants, lycopene stability in oil‐in‐water emulsions could be significantly improved. Practical applications: Evidence that dietary lycopene decreases the risk for a number of health conditions has generated new opportunities for addition of lycopene to functional foods. A successful strategy to deliver lycopene into foods is by means of oil‐in‐water emulsions. However, lycopene may decompose thus causing nutritional loss and color fading. In order to prevent this, the effectiveness of various antioxidants and their combinations in Tween 20 stabilized oil‐in‐water emulsions was studied. Overall, lycopene oxidation in oil‐in‐water emulsions could be significantly reduced by the proper selection of free radical scavengers. This fact is of interest to food industry for increasing the shelf‐life of lycopene containing functional foods where the lycopene is dispersed in the food in the form of an oil‐in‐water emulsion.     

Formation of Acrolein in the Autoxidation of Triacylglycerols with Different Fatty Acid Compositions

Fish, echium, linseed, and soybean oil triacyglycerols (TAGs) were oxidized at 50 or 60 °C to determine the effect of the polyunsaturated fatty acid composition on the volatile product formation. The analysis of the oxygen consumption and total volatile formation demonstrated that the soybean oil TAG had the highest oxidative stability followed by linseed, echium, and fish oil TAGs. Our results were in agreement with the expected average number of bis‐allylic positions of each TAG. Higher quantities of acrolein (2‐propenal) and propanal were detected using the static headspace gas chromatography method at the early stages of oxidation of echium and fish oil TAGs; however, a considerable amount of propanal and only a small amount of acrolein were found in the oxidized linseed oil TAG. The peak area ratios of acrolein to propanal were 0.115, 0.569, and 2.554 after the 8‐h oxidation of linseed, echium, and fish oil TAG, respectively, suggesting the preferential formation of acrolein, especially during the fish oil TAG oxidation. The acrolein quickly increased during the first stage of oxidation, but thereafter it either did not change or slightly decreased during the fish oil oxidation. Because fish oil induces flavor deterioration from the very early stage of the oxidation, the acrolein formation observed in the present study may be important for fish oil deterioration.