Formation Of Oxidation Products Research Articles

THE RELATIONSHIP BETWEEN OXIDATIVE STRESS AND NEUROLOGICAL DISORDERS: MINI REVIEW

Oxidative stress is one of the main causes of neuronal dysfunction and death, mainly due to excessive formation of reactive oxygen species and depletion of antioxidant reserves. Oxidative stress is characterized by an imbalance between the production of reactive oxygen species (ROS) and antioxidant defense mechanisms of the body. This process is involved in the onset and development of many neurological diseases. In this review, we analyzed and summarized the results of studies showing the association of neurological diseases, such as stroke, Parkinson’s disease, and other neurological diseases, with excessive formation of oxidative stress products. This article aims to provide an overview of the relationship between oxidative stress and a range of neurological conditions, shedding light on the underlying mechanisms and potential therapeutic implications.

Difference comparison of characteristic aroma compounds between braised pork cooked by traditional open-fire and induction cooker and the potential formation cause under electromagnetic cooking

The characteristic aroma compounds of braised pork were identified through molecular sensory science and PLSR analysis, and the difference between two cooking methods, traditional open-fire (BPF) and induction cooker (BPC), was compared. Seventeen aroma compounds with odor activity values (OAVs) > 1 were identified in both samples. BPF revealed higher OAVs for most of the aroma compounds compared to BPC, and the higher aroma quality. Aroma recombination and omission experiments confirmed that twelve aroma compounds significantly contributed to the characteristic aroma of braised pork, and eight compounds such as hexanal, (E)-2-octenal, and methanethiol were further confirmed as important contributors by PLSR analysis. Furthermore, PLSR analysis clarified the role of aldehydes such as hexanal, (E)-2-octenal, and (E,E)-2,4-decadienal in contributing to fatty attribute, whereas methanethiol was responsible for the meaty aroma. These characteristic aroma compounds mainly derived from lean meat due to its high content of phospholipids, and the exogenous seasonings contributed to the balanced characteristic aroma profile of braised pork by altering the distribution of these characteristic aroma compounds. Variations in heating parameters affected the formation of lipid oxidation and Strecker degradation products, which might explain aroma discrepancy between braised pork cooked by two methods with different heat transfer efficiencies.

L-proline Interaction with Methyl Linoleate Oxidation Products Formation in Dry System and at Temperatures: For Understanding in Low-Moisture Foods

Dry and low-moisture foods could experience a significant loss in nutritional value due to the process of methyl linoleate oxidation. L-proline could interact with lipid oxidation products, potentially modifying their formation and reaction path. However, there was a lack of research on the interaction between L-proline and methyl linoleate oxidation products in dry and low-moisture food matrices, which was a concern given the potential impact on food safety and nutrition. To address this knowledge gap, a study investigated the interaction between L-proline and the oxidation products of methyl linoleate in a dry system. The study examined the formation of methyl linoleate oxidation products such as conjugated dienes, hydroperoxide, and hexanal in the absence and presence of varying moles of L-proline at different temperatures. The formation of conjugated diene, hydroperoxide, and hexanal was analyzed using UV spectrometer analysis, xylenol orange, and DNPH derivatization HPLC-UV analysis. The results showed that adding proline to methyl linoleate samples stabilized conjugated diene and decreased hydroperoxide and hexanal levels as temperature increased, compared to the control sample. This suggests that L-proline effectively interacted with methyl linoleate oxidation products and altered their formation and oxidation path in the dry system. Overall, this study provided a basis for significantly enhancing understanding of the reactions between L-proline and methyl linoleate oxidation products in dry and low-moisture foods, offered practical implications for the food industry, and paved the way for future research.

A mechanistic kinetic model for lipid oxidation in Tween 20-stabilized O/W emulsions

Models predicting lipid oxidation in oil-in-water (O/W) emulsions are a requirement for developing effective antioxidant solutions. Existing models do, however, not include explicit equations that account for composition and structural features of O/W emulsions. To bridge this gap, a mechanistic kinetic model for lipid oxidation in emulsions is presented, describing the emulsion as a one-dimensional three phase (headspace, water, and oil) system. Variation in oil droplet sizes, overall surface area of oil interface, oxidation of emulsifiers, and the presence of catalytic transition metals were accounted for. For adequate predictions, the overall surface area of oil interface needs to be determined from the droplet size distribution obtained by dynamic and static light scattering (DLS, SLS). The kinetic model predicted well the formation of oxidation products in both mono- and polydisperse emulsions, with and without presence of catalytic transition metals.

Comparing the Aging Processes of PLA and PE: The Impact of UV Irradiation and Water

The aging processes of microplastics (MPs) are prevalent in natural environments. Understanding the aging mechanisms of MPs is crucial for assessing their environmental behavior and potential risks. In this study, we selected polylactic acid (PLA) and polyethylene (PE) as representatives of biodegradable and conventional plastics, respectively, to examine changes in their physicochemical properties induced by water and UV light exposure. Laboratory aging resulted in significant fragmentation, characterized by cracks and pores on the surfaces, for both types of MPs, with PLA MPs exhibiting more severe changes, particularly under combined UV and water exposure. Notably, PLA MPs tended to become progressively smaller after aging, whereas PE MPs did not show significant size changes. Chemical analyses of aged MPs using micro-Fourier-transform infrared spectroscopy (FTIR) and X-ray photoelectron spectroscopy (XPS) revealed a substantial increase in the carbonyl index (CI) and oxygen content for PE, suggesting surface oxidation during photo-oxidation. Conversely, PLA MPs displayed a CI decrease, along with an oxygen content increase, indicating the breakdown of ester linkages in PLA and the formation of other oxidation products. Furthermore, we developed and optimized pyrolysis–gas chromatography–mass spectrometry (Py–GC–MS) methods to identify potential chemical degradation products of PE and PLA, considering their differing thermal stabilities. We observed a distinct trend regarding the peaks in the chromatogram of aged MPs and identified the typical oxidation and crosslinking products for PLA. Additionally, after the aging process, both PE and PLA exhibited a significant increase in organic carbon content, with the eluate containing submicron/nano-sized particles. This study provides a scientific foundation for a deeper understanding of the environmental aging mechanisms of various MPs, particularly in regards to the effects of UV irradiation and water exposure.

Insight into the Structure and Redox Chemistry of [Carbonatotetraamminecobalt(III)] Permanganate and Its Monohydrate as Co-Mn-Oxide Catalyst Precursors of the Fischer-Tropsch Synthesis

[Carbonatotetraamminecobalt(III)] permanganate monohydrate was synthesized first in the metathesis reaction of [Co(NH3)4CO3]NO3 and NaMnO4 in aqueous solution. Its thermal dehydration at 100 °C resulted in phase-pure [Co(NH3)4CO3]MnO4 (compound 1). Compounds 1 and 2 (i.e., the hydrated form) were studied with IR, far-IR, and low-temperature Raman spectroscopies, and their vibrational modes were assigned. The lattice parameters were determined by powder X-ray diffraction (PXRD) and single crystal X-ray diffraction (SXRD) methods for the triclinic and orthorhombic compounds 1 and 2, respectively. The detailed structure of compound 2 was determined, and the role of hydrogen bonds in the structural motifs was clarified. UV studies on compounds 1 and 2 showed the distortion of the octahedral geometry of the complex cation during dehydration because of the partial loss of the hydrogen bonds between the crystal water and the ligands of the complex cation. The thermal decomposition consists of a solid phase quasi-intramolecular redox reaction between the ammonia ligands and permanganate anions with the formation of ammonia oxidation products (H2O, NO, N2O, and CO2). The solid phase reaction product is amorphous cobalt manganese oxide containing ammonium, carbonate (and nitrate) anions. The temperature-controlled thermal decomposition of compound 2 in toluene at 110 °C showed that one of the decomposition intermediates is ammonium nitrate. The decomposition intermediates are transformed into Co1.5Mn1.5O4 spinel with MnCo2O4 structure upon further heating. Solid compound 2 gave the spinel at 500 °C both in an inert and air atmosphere, whereas the sample pre-treated in toluene at 110 °C without and with the removal of ammonium nitrate by aqueous washing, gave the spinel already at 300 and 400 °C, respectively. The molten NH4NO3 is a medium to start spinel crystallization, but its decomposition stops further crystal growth of the spinel phase. By this procedure, the particle size of the spinel product as low as ~4.0 nm could be achieved for the treatments at 300 and 400 °C, and it increased only to 5.7 nm at 500 °C. The nano-sized mixed cobalt manganese oxides are potential candidates as Fischer-Tropsch catalysts.

Photoaged polystyrene nanoplastics exposure results in reproductive toxicity due to oxidative damage in Caenorhabditis elegans

The increase of plastic production together with the incipient reuse/recycling system has resulted in massive discards into the environment. This has facilitated the formation of micro- and nanoplastics (MNPs) which poses major risk for environmental health. Although some studies have investigated the effects of pristine MNPs on reproductive health, the effects of weathered MNPs have been poorly investigated. Here we show in Caenorhabditis elegans that exposure to photoaged polystyrene nanoplastics (PSNP-UV) results in worse reproductive performance than pristine PSNP (i.e., embryonic/larval lethality plus a decrease in the brood size, accompanied by a high number of unfertilized eggs), besides it affects size and locomotion behavior. Those effects were potentially generated by reactive products formed during UV-irradiation, since we found higher levels of reactive oxygen species and increased expression of GST-4 in worms exposed to PSNP-UV. Those results are supported by physical-chemical characterization analyses which indicate significant formation of oxidative degradation products from PSNP under UV-C irradiation. Our study also demonstrates that PSNP accumulate predominantly in the gastrointestinal tract of C. elegans (with no accumulation in the gonads), being completely eliminated at 96 h post-exposure. We complemented the toxicological analysis of PSNP/PSNP-UV by showing that the activation of the stress response via DAF-16 is dependent of the nanoplastics accumulation. Our data suggest that exposure to the wild PSNP, i.e., polystyrene nanoplastics more similar to those actually found in the environment, results in more important reprotoxic effects. This is associated with the presence of degradation products formed during UV-C irradiation and their interaction with biological targets.

The effect of gamma radiation on 5-hydroxymethylfurfural conversion in water and dimethyl sulfoxide

Abstract 5-Hydroxymethylfurfural (HMF) is a biomass-based chemical platform that can undergo many feasible reactions. One of the most important reactions is the oxidation to 2,5-furandicarboxylic acid (FDCA), which is the monomer for bioplastic production. In this work, the radiation method was used to investigate the conversion of HMF in both aqueous (DI) and dimethyl sulfoxide (DMSO) solutions. The effects of media solvents, atmospheric gases, HMF concentrations, additive bases, and absorbed doses of gamma radiation were studied. The results showed that the media solvent played a crucial role in HMF conversion under gamma irradiation. At 30 kGy, the HMF conversions in DI and DMSO were 92.1 and 24.1%, respectively, and the oxidation products were only found in the irradiated samples under DMSO. The HMF conversion and oxidation product formation increased with the gamma radiation dose. Moreover, it was found that FDCA stability toward gamma irradiation is highly sensitive in aqueous solution but relatively stable in DMSO. The results implied the alternative promising choice of radiation method compared with traditional methods. To join the bridge, the use of a mixture solvent DI/DMSO seems considerable in the future.

Quantification of Hop-Derived Bitter Compounds in Beer Using Liquid Chromatography Mass Spectrometry.

Hops (Humulus lupulus L.) are essential raw materials for beer brewing, and the major contributors to beer bitterness are isohumulones (iso-α-acids) and humulinones. In recent years, many breweries have focused on the production of hop-forward beer styles by adding hops after or during the cold fermentation stage, which will tend to release humulinones or other hop-derived bitter compounds. In this study, a LC-MS/MS method was developed for quantification of 60 hop-derived bitter compounds in 25 min. Reverse-phase chromatography with an alkaline methanol/acetonitrile (70:30) mobile phase was used for the separation. The quantitative range was 0.053-3912 ng/mL with correlation coefficient r > 0.99, and the LOQ were 0.26 and 0.053 ng/mL for iso-α-acids and humulinones. Precision (RSD < 5.0%) and accuracy (recovery 86.3%-118.1%) were both satisfactory. The abundance of hop-derived bitter compounds in the dry-hopped beer (Double-India Pale Ale) and the nondry-hopped beer (Vienna Lager) were monitored throughout the fermentation and storage stages, and the formation of oxidation and cyclization products showed difference profiles between these two beers. The quantification results reveal how hop-derived bitter compounds change throughout the brewing process, as well as the influence of hops and brewing techniques on beer bitterness.

Mathematical Modeling of Alpha-Tocopherol Early Degradation Kinetics to Predict the Shelf-Life of Bulk Oils.

The kinetics of lipid oxidation includes a lag phase followed by an exponential increase in oxidation products, which cause rancidity. Current models focus on the slope of this exponential curve for shelf-life estimation, which still requires the measurement of full oxidation kinetics. In this paper, we analyzed the formation of lipid oxidation products in stripped soybean oil containing different levels of α-tocopherol. The lag phases of lipid hydroperoxides and headspace hexanal formation were found to have a strong positive correlation with the α-tocopherol depletion time. We propose that the kinetics of antioxidant (α-tocopherol) depletion occur during the lag phase and could serve as an early shelf-life indicator. Our results showed that α-tocopherol degradation can be described by Weibull kinetics over a wide range of initial concentrations. Furthermore, we conducted in silico investigations using Monte Carlo simulations to critically evaluate the feasibility and sensitivity of the shelf-life prediction using early antioxidant degradation kinetics. Our results revealed that the shelf life of soybean oil may be accurately predicted as early as 20% of the overall shelf life. This innovative approach provides a more efficient and faster assessment of shelf life, ultimately reducing waste and enhancing product quality.

Protective effect of colchicine on albumin glycation and cellular oxidative stress: Insights into diabetic cardiomyopathy.

The present work elucidates the role of colchicine (COL) on albumin glycation and cellular oxidative stress in diabetic cardiomyopathy (DCM). Human serum albumin (HSA) was glycated with methylglyoxalin the presence of COL (2.5, 3.75, and 5 µM), whereas positive and negative control samples were maintained separately. The effects of COL on HSA glycation, structural and functional modifications in glycated HSA were analyzed using different spectroscopical andfluorescence techniques. Increased fructosamine, carbonyl, and pentosidine formation in glycated HSA samples were inhibited in the presence of COL. Structural conformation of HSA and glycated HSA samples was examined by field emission scanning electron microscopy, circular dichroism, Fourier transform infrared, and proton nuclear magnetic resonance analyses, where COL maintained both secondary and tertiary structures of HSA against glycation. Functional marker assays included ABTS•+ radical scavenging and total antioxidant activities, advanced oxidative protein product formation, and turbidimetry, which showed preserved functional properties of glycated HSA in COL-containing samples. Afterward, rat cardiomyoblast (H9c2 cell line) was treated with glycated HSA-COL complex (400 μg/mL) for examining various cellular antioxidants (nitric oxide, catalase, superoxide dismutase, and glutathione) and detoxification enzymes (aldose reductase, glyoxalase I, andII) levels. All three concentrations of COL exhibited effective anti-glycation properties, enhanced cellular antioxidant levels, and detoxification enzyme activities. The report comprehensively analyzes the potential anti-glycation and properties of COL during its initial assessment.

Alcoholic beverages reduce oxidation during in vitro gastrointestinal digestion of meat and fish, but induce fatty acid ethyl ester formation

The effect of selected phenolic-containing beers (pale lager, barley wine, tripel), white wine, and red wine on the formation of lipid oxidation products (thiobarbituric acid reactive substances, 4-hydroxy-2-hexenal, 4-hydroxy-2-nonenal) and protein carbonylation during simulated gastrointestinal digestion of pork and salmon was investigated. Greater antioxidant effects of the beverages were observed during the digestion of salmon, whereas antioxidant effects were less pronounced or absent during the digestion of pork. Red wine contained the highest levels of phenolics, accompanied by the highest antioxidant effects among the beverages tested. Secondly, the simultaneous formation of potentially harmful fatty acid ethyl esters (FAEEs) was observed for the first time when these muscle foods were digested with the beers and wines tested, or with pure ethanol. These FAEEs were formed by lipase activity in the presence of ethanol, which was blocked by the lipase inhibitor orlistat. The formation of selected FAEEs corresponded well with the levels of their precursor fatty acids in muscle, resulting in different FAEE profiles in the digests of chicken, pork, beef, or salmon with ethanol. In conclusion, the formation of potentially harmful FAEE may counteract the observed beneficial antioxidant effects of phenolic-rich alcoholic beverages during the gastrointestinal digestion of muscle foods.

Jussara palm tree (Euterpe edulis M.) açai-berry oil performance on auto- and photo-oxidation: Minor components’ stability and evolution of volatile compounds

The oxidative stability of açai-berry oil relating with the formation of oxidation products, the stability of minor components, and the evolution of volatile compounds under accelerated auto- and photo-oxidation was investigated. In both tests, peroxide value increased linearly with time and was negatively associated (R² ≥ 0.98) with α- and β-tocopherols, and chlorophyll a. γ-Tocopherol was one of the most unstable compounds, reaching complete loss between 0-to-3 days in auto-oxidation, and between 3-to-5 days in photo-oxidation. α-Tocopherol remained stable during auto-oxidation whereas β-Tocopherol degraded from 5-to-7 days, reaching 57 % loss. At 7 days of photo-oxidation, α-Tocopherol reached a small 26 % loss and β-Tocopherol a 32 % loss. Anthocyanins content decayed exponentially with time, reaching a 93 % loss after 7 days of auto-oxidation and a complete loss between 0-to-3 days of photo-oxidation. Hexanal and nonanal were formed in the advanced stages of auto-oxidation and in early stages of photo-oxidation, reaching after 7 days of oxidation contents that were over 15-fold and over 7-fold higher in the later than in the former. Conversely, 2-heptenal was formed only in photo-oxidation. Açai-berry oil was highly stable in auto-oxidation in the dark, but it requires storage under protection from light due to its low photo-oxidation stability.

Chemical characterization of sunflower oil oxidized by UV and ozone with different degrees of oxidation and study of their antimicrobial action

Oxidation by the action of ozone takes place at high rates and involves the reaction of ozone molecules with fatty acid double bonds followed by the formation of stable oxidation products with biological activity. In the present work, a comparative study on sunflower oil oxidized by ultraviolet (UV) light and ozone was carried out. This study involved the chemical characterization of sunflower oil oxidized by UV irradiation and ozonation, in addition to assessing the germicidal activity of oxidized oils obtained under various conditions. The results indicated that under the conditions studied, the increase in the dose of UV irradiation did not produce significant changes in the level of oxidation of the oil. Ozonation promoted the formation of oxygenated compounds at higher rates, increasing in concentration as the applied dosage of ozone increased. The germicidal activity of the oils behaved similarly, with considerably higher activity found in the ozonized oils.

Mechanisms of the Formation of Nonvolatile and Volatile Oxidation Products from Methyl Linoleic Acid at High Temperatures.

The impact of the oxidation of linoleic acid cannot be overlooked in daily food consumption. This study used gas chromatography-mass spectrometry (GC-MS) to identify both nonvolatile oxidation products and volatile oxidation products of methyl linoleic acid at 180 °C and density function theory to investigate oxidation mechanisms. An analysis of nonvolatile oxidation products revealed the presence of three primary oxidation products. The three primary oxidation products were identified as hydroperoxides, peroxide-linked dimers, and heterocyclic compounds in a ratio of 2.70:1:3.69 (mmol/mmol/mmol). The volatile components of secondary oxidation products were found including aldehydes (40.77%), alkanes (19.89%), alcohols (9.02%), furans (6.11%), epoxides (0.46%), and acids (2.50%). DFT calculation proved that the secondary oxidation products mainly came from peroxides (77%). Finally, we look forward to our research contributing positively to lipid autoxidation and human health.

Unraveling the oxidation behavior and mechanism of (TiZrTaNbCr)C high-entropy ceramic by introducing Cr3C2

High-entropy carbide ceramic materials exhibited excellent thermal and mechanical properties, making them highly sought after in high-temperature applications. However, the oxidation resistance of high-entropy carbide ceramic needed to be further improved. This work unraveled the oxidation behavior and mechanism of high-entropy carbide ceramic by introducing the Cr3C2. The results indicated that the oxidation rate of (TiZrTaNbCr)C initially decreased with temperature up to 900 °C, followed by an increased with further temperature rise up to 1100 °C. At 800 and 900 °C, the parabolic oxidation rate constants were 0.70 and 0.17 mg2cm−4min−1, respectively. And the minimum thickness of oxidized layer was 60 µm at 900 °C for 120 min. This unusual phenomenon suggested the formation of different oxidation products. Specifically, the CrNbO4 and Nb2Zr6O17 oxide layer were formed at 900 °C, leading to an increased resistance to oxygen diffusion. Subsequently, loose oxidation products of Nb2O5 were formed after 1000 °C, hindering the oxidation resistance. In the current study on oxidation resistance of high entropy carbides, this work showed a competitive performance. Overall, this study illustrated the oxidation mechanism and behavior of (TiZrTaNbCr)C and proposed a new avenue for the design of high-entropy ceramic components.

Antioxidant peptides from alternative sources reduce lipid oxidation in 5% fish oil-in-water emulsions (pH 4) and fish oil-enriched mayonnaise.

Bioinformatics tools were used to predict radical scavenging and metal chelating activities of peptides derived from abundant potato, seaweed, microbial, and spinach proteins. The antioxidant activity was evaluated in 5% oil-in-water emulsions (pH4) and best-performing peptides were tested in mayonnaise and compared with EDTA. Emulsion physical stability was intact. The peptide DDDNLVLPEVYDQD showed the highest protection against oxidation in both emulsions by retarding the formation of oxidation products and depletion of tocopherols during storage, but it was less efficient than EDTA when evaluated in mayonnaise. In low-fat emulsions, formation of hydroperoxides was reduced 4-folds after 5days compared to control. The concentration effect of the peptide was confirmed in mayonnaise at the EDTA equimolar concentration. The second-best performing peptides were NNKWVPCLEFETEHGFVYREHH in emulsion and AGDWLIGDR in mayonnaise. In general, the peptide efficacy was higher in low-fat emulsions. Results demonstrated that peptide negative net charge was important for chelating activity.

Impact of frozen storage on quality and cold storage stability of smoked deep-skinned fillets from well-fed Atlantic mackerel

To ensure year-round availability and stability of Atlantic mackerel caught in Icelandic waters during summer after intensive feeding, freezing is essential. Due to the high lipid content and sensitive lipid composition of the fish caught at this time, the fish industry requires detailed research to understand the mechanisms underlying the degradation processes occurring during storage and processing, in order to develop high-value hot-smoked products. Therefore, the impact of frozen storage at − 25 ± 1.8 °C (for 6, 9, and 20 months) prior to hot-smoking, was investigated on the physicochemical, microbial, and sensory quality of deep-skinned, smoked fillets from well-fed Atlantic mackerel caught in late August. The stability of hot-smoked fillets stored at 1 ± 0.6 °C was then monitored for 28 days. Total aerobic viable counts (TVC) remained below acceptable thresholds due to the combined effects of brining, freezing, and hot-smoking, while Listeria monocytogenes was not detected in the hot-smoked products. Slow formation of oxidation products was observed during the chilled storage, especially in the fish frozen for 9 months. Minor lipid deterioration was also detected during sensory analysis, but all spoilage indices remained within acceptable thresholds for shelf-life. Frozen storage for up to 20 months thus effectively maintained the sensory acceptability and suitability of deep-skinned mackerel fillets, making them an excellent choice for the fish-smoking industry.

The degradation of 1,4 acetaminophen by electrocatalytic oxidation process and investigation the by-products of the system

The study was aimed at using Ti/IrO2-RuO2 electrocatalytic electrodes for the purpose of removing 1,4-acetaminophen from a solution. The electrooxidation process's efficiency was studied by controlling various parameters such as pH (3−11), current density (100–1000 A.m-2), electrolyte type (NaCl, Na2SO4, KCl), and conductivity (1.5–10 mS.cm-1). Additionally, H2O2 addition (100–1000 µL), and acetaminophen concentration (25–100 ppm) were also studied. In addition, it was found that when the initial concentrations were increased from 25 ppm to 100 ppm, there was a corresponding increase in the removal efficiencies, which ranged from 27% to 36% at a current density of 350 A.m-2 and a conductivity of 3.5 mS.cm-1 for a period of 90 min. The removal efficiency increased from 30% to 42% when 0.5 mL of 30% H2O2 was added to the initial concentration of 50 ppm. The presence of chlorine ions in a solution has been demonstrated to result in the formation of oxidation products. This result has enabled researchers to investigate the toxic and disinfecting properties of the solution. The LC-MS spectra analysis revealed the formation of intermediate degradation products. The identification of these metabolites enabled the suggestion of their structure and degradation mechanism.

Synthesis of lipoic acid ferulate and evaluation of its ability to preserve fish oil from oxidation during accelerated storage.

Lipoic acid ferulate (LAF) was synthesized and its anti-free radical ability in vitro was determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2-azino-bis (3-ethylbenzothiazoline-6-sulfonicacid) (ABTS) assays. Protective effects of LAF in stabilizing fish oil were tested, compared to antioxidants such as lipoic acid, ferulic acid and tert-butylhydroxyquinone (TBHQ) by measuring peroxide values, thiobarbituric acid reactants, p-anisidine values, nuclear magnetic resonance (NMR) spectra and gas chromatography-mass spectrometry (GC-MS) spectra of fish oil during accelerated storage (12days, 80°C). The inhibitory effect of these antioxidants on fish oil oxidation followed the order TBHQ ≧ LAF>ferulic acid>lipoic acid. In addition, the omega-3 polyunsaturated fatty acids were the first to be oxidized. The formation of oxidation products followed a first-order kinetic model, and the addition of LAF effectively reduced the reaction rate constants. Therefore, LAF can effectively slow down the formation of oxidative products and prolong the shelf life of fish oil.