Effect of Interfacial Activity of Eugenol and Eugenol Esters with Different Alkyl Chain Lengths on Inhibiting Sunflower Oil Oxidation

Abstract

Effects of eugenol esters with different alkyl chain lengths and combinations of eugenol + eugenol esters on sunflower oil oxidation at 338, 358, and 378 K are evaluated by determining different kinetic parameters. Also, water content and reverse micelles size of sunflower oil samples are monitored during oxidation. Eugenyl acetate shows higher antioxidant activity than eugenol in sunflower oil, while eugenyl butyrate, eugenyl hexanoate, and eugenyl decanoate shows lower antioxidant activity than eugenol. Antioxidant activity of eugenol esters decreases by increasing their alkyl chain length. Eugenol shows a synergistic effect with eugenyl acetate and eugenyl butyrate on increasing the induction period and antioxidant activity values, while it shows an antagonistic effect with eugenyl hexanoate and eugenyl decanoate. Also, combinations of eugenol + eugenyl acetate, as well as, eugenol + eugenyl butyrate stabilize the reverse micelles at longer period of time (3263 min for eugenol + eugenyl acetate and 2900 min for eugenol + eugenyl butyrate) than eugenol (2750 min). In addition, eugenol + eugenyl acetate and eugenol + eugenyl butyrate decrease the magnitude of temperature-related effects on sunflower oil oxidation to the higher extent than eugenol did. Practical applications: Recent studies have suggested that the antioxidants with ability to locate at the active sites of lipid oxidation can efficiently reduce lipid oxidation in bulk oil. Despite a remarkable focus on antioxidant activity of eugenol, there is no information regarding improving its interfacial performance through esterification method. Also, there are few published data regarding the effects of esterified antioxidants on physicochemical changes during the oxidation of bulk oil. In this study, eugenol is esterified with anhydrides with different alkyl chain lengths to increase its accessibility to the active site of lipid oxidation, that is, water-oil interface of reverse micelles in sunflower oil. Effects of eugenol esters on stability of reverse micelles and critical reverse micelles concentration of lipid hydroperoxides have been investigated for the first time.

Kinetic and thermodynamic parameters of curcumin in edible oils with different degrees of unsaturation

“…It has been confirmed that the general trend of the oxidation process tends to change at temperatures higher than 60 °C (Zheng et al, 2020). Although the reaction rate also increases, the effect of the pathway change is much higher than the reaction rate (Keramat et al, 2021). Second, the effects of temperature on antioxidant molecules which can cause decomposition or evaporation.…”

Comparison of the antioxidant capacity of sesamol esters in gelled emulsion and non-gelled emulsion

“…Then, excess of anhydrides and produced acids were evaporated from the mixture by evaporation under vacuum. Sesamol esters purity (>95%) was measured via gas chromatography/flame ionization detector by the method of Keramat, Golmakani, and Toorani (2021) .…”

Recent Trends in Improving the Oxidative Stability of Oil-Based Food Products by Inhibiting Oxidation at the Interfacial Region

“…This indicates and describes the synergy contribution to the inhibition of chain initiation and/or propagation reactions and the likelihood of their promoted incorporations into the interfacial area of association colloids [ 56 ]. Additionally, sunflower oil samples containing eugenol + eugenyl acetate and eugenol and eugenyl butyrate exhibited better efficiency than eugenol alone, which could be related to the better accessibility of eugenol to the interfacial region of the reverse micelles when eugenyl acetate and eugenyl butyrate are present [ 57 ].…”