On the kinetics of the autoxidation of fats: influence of pro‐oxidants, antioxidants and synergists

Brimberg, Ulla I.; Kamal‐Eldin, Afaf

doi:10.1002/ejlt.200390021

Cited by 45 publications

(21 citation statements)

References 31 publications

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“…Of course this must be evaluated in virgin olive oil, a subject currently under investigation. It is important to note that equations (1) to (4) are not intended to define the chemical mechanisms of the reactions that actually take place during autoxidation as proposed by other authors [21][22][23]. They are simple empirical equations that could be used to predict with reasonable accuracy the concentration of relevant oxidized components, and hence the time required to reach a given value in an oxidation or quality index under normal storage conditions (shelf-life), from the results of an ASLT.…”

Section: Shelf-life Predictionmentioning

confidence: 98%

Oxidation kinetics in olive oil triacylglycerols under accelerated shelf‐life testing (25–75 °C)

Gómez‐Alonso

Mancebo‐Campos

Salvador

et al. 2004

Euro J Lipid Sci & Tech

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A kinetic study of the autoxidation reaction in olive oil triacylglycerols stored in darkness at different temperatures (25, 40, 50, 60 and 75 7C), in absence of pro-and antioxidant compounds to avoid confounding effects, is described. After the induction period (IP) the decrease in the oxidizing substrate and the formation of primary oxidation products followed a pseudo-zero-order kinetic, and the calculated E a from the Arrhenius equation for the formation of hydroperoxides was 32.1 kJ?mol 21 . The formation of secondary oxidation products followed a pseudo-first-order kinetic whose rate reaction constant also increased exponentially with temperature. The first oxidation index to exceed the upper limit in the EU regulations was PV, followed by K 232 and K 270 . The time required reaching these limits and the rancidity threshold showed a potential dependence on temperature, and therefore with accelerated storage at 75 7C, POO shelf-life in ambient conditions (25 7C) can be predicted. Finally, there was a good linear relationship between the time required to reach the rancidity threshold and the IP of the formation of the 2,4-decadienal, and hence this instrumental determination could be useful to measure sensory recognition of the rancid defect in POO.

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Section: Shelf-life Predictionmentioning

confidence: 98%

Oxidation kinetics in olive oil triacylglycerols under accelerated shelf‐life testing (25–75 °C)

Gómez‐Alonso

Mancebo‐Campos

Salvador

et al. 2004

Euro J Lipid Sci & Tech

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“…When the surface‐to‐volume ratio increases, the relative rate of oxidation is less oxygen‐dependent with a low oxygen content. The container surface can act as a reduction catalyst, and its effect was shown to be proportional to the area of the container in contact with the oils (Brimberg and Kamal‐Eldin 2003).…”

Section: Factors Affecting the Oxidation Of Edible Oilmentioning

confidence: 99%

“…Sesame oil also contains phytosterols such as campesterol, stigmasterol, β‐sitosterol, and 4,5‐avenasterol, with β‐sitosterol as the predominant sterol (Dachtler and others 2003). Sitosterol behaves partly as a prooxidant by increasing the solubility of oxygen in the oil (Yanishlieva and Schiller 1983) and partly as a weak antioxidant in sunflower oil and lard by competing with lipid molecules for oxidation at the oil surface (Maestroduran and Borjapadilla 1993; Brimberg and Kamal‐Eldin 2003).…”

Section: Factors Affecting the Oxidation Of Edible Oilmentioning

confidence: 99%

Mechanisms and Factors for Edible Oil Oxidation

Choe¹,

Min²

2006

Comp Rev Food Sci Food Safe

1,491

1,210

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Edible oil is oxidized during processing and storage via autoxidation and photosensitized oxidation, in which triplet oxygen ( 3 O 2 ) and singlet oxygen ( 1 O 2 ) react with the oil, respectively. Autoxidation of oils requires radical forms of acylglycerols, whereas photosensitized oxidation does not require lipid radicals since 1 O 2 reacts directly with double bonds. Lipid hydroperoxides formed by 3 O 2 are conjugated dienes, whereas 1 O 2 produces both conjugated and nonconjugated dienes. The hydroperoxides are decomposed to produce off-flavor compounds and the oil quality decreases. Autoxidation of oil is accelerated by the presence of free fatty acids, mono-and diacylglycerols, metals such as iron, and thermally oxidized compounds. Chlorophylls and phenolic compounds decrease the autoxidation of oil in the dark, and carotenoids, tocopherols, and phospholipids demonstrate both antioxidant and prooxidant activity depending on the oil system. In photosensitized oxidation chlorophyll acts as a photosensitizer for the formation of 1 O 2 ; however, carotenoids and tocopherols decrease the oxidation through 1 O 2 quenching. Temperature, light, oxygen concentration, oil processing, and fatty acid composition also affect the oxidative stability of edible oil.

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“…Gradually, a change in paradigm occurred in relation to these criticalities. Several breakthroughs have led to this change starting with the publication of Porter's () treatise on the antioxidant paradox, Frankel and others () suggestion of the interfacial phenomenon, and its refining by Decker's group to include association colloids (Chaiyasit and others , ; Chen and others , ); the cut‐off theory (Laguerre and others , ), and the involvement of micelles (Brimberg and Kamal‐Eldin ; Budilarto and Kamal‐Eldin , ).…”

Section: Lipid Oxidation As Explained By the Free Radical Mechanismmentioning

confidence: 99%

“…The main reactions responsible for the peroxidative effect of α‐tocopherol were shown to include chain transfer reaction at the abstraction of hydrogen atom from the fatty acid molecule and from the hydroperoxide by tocopheroxyl radical, an initiation reaction involving a reducing effect of α‐tocopherol on hydroperoxides, and reactions of homolytic decomposition of quinolide peroxides (Tavadyan and others ). However, because of the surfactants and anti‐coagulation effect of α‐tocopherol (log P = 9.04), the CMC is higher in samples containing tocopherols compared to controls or samples containing low concentrations of the antioxidant (Brimberg and Kamal‐Eldin ). Thus, the presence of high concentrations of α‐tocopherol contributes to decreasing the interfacial tension and stabilizing the micelles, which explains why it prolongs the induction period despite the increase of the rate of oxidation during the induction period.…”

Section: The Participation Of Different Molecular Species In the Oxidmentioning

confidence: 99%

The New Paradigm for Lipid Oxidation and Insights to Microencapsulation of Omega‐3 Fatty Acids

Ghnimi

Budilarto

Kamal‐Eldin

2017

Comp Rev Food Sci Food Safe

120

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The consumption of omega-3 fatty acids provides a wide range of health benefits. However, the incorporation of these fatty acids in foods is limited because of their high oxidative instability. A new paradigm has emerged to better explain the oxidation mechanism of polyunsaturated fatty acids, which will be discussed here with reference to bulk lipids considered a special case of water in oil microemulsion. This paradigm suggests that lipid oxidation reactions are initiated by heterogeneous catalysis by metal oxides followed by the formation of micelles containing initial hydroperoxides, water, and other amphiphilic compounds. The induction period comes to the end when the formed micelles reach a critical micelle concentration and start to decompose opening the way to intense free radical reactions. Antioxidants and synergists extend the induction period not only by scavenging free radicals but also by stabilizing the micelles. With better understanding of the lipid oxidation mechanism, a tailored choice of antioxidants and synergistic combinations, and efficient encapsulation methods may be optimized to provide stable encapsulates containing highly n-3 polyunsaturated fatty acids. Smart processing and encapsulation technologies utilizing properly stabilized oils as well as optimized packaging parameters aiming to enhance n-3 fatty acid stability by smart selection/design of antioxidants, control of the interfacial physics and chemistry, and elimination of surface oil are needed for this purpose.

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On the kinetics of the autoxidation of fats: influence of pro‐oxidants, antioxidants and synergists

Cited by 45 publications

References 31 publications

Oxidation kinetics in olive oil triacylglycerols under accelerated shelf‐life testing (25–75 °C)

Oxidation kinetics in olive oil triacylglycerols under accelerated shelf‐life testing (25–75 °C)

Mechanisms and Factors for Edible Oil Oxidation

The New Paradigm for Lipid Oxidation and Insights to Microencapsulation of Omega‐3 Fatty Acids

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