Limonene, linalool and citral are common non-phenolic terpenoid components of essential oils, with attributed controversial antioxidant properties. The kinetics of their antioxidant activity was investigated using the inhibited autoxidation of a standard model substrate. Results indicate that antioxidant behavior of limonene, linalool and citral occurs by co-oxidation with the substrate, due to very fast self-termination and cross-termination of the oxidative chain. Rate constants kp and 2kt, (M−1 s−1) at 30 °C were 4.5 and 3.5 × 106 for limonene, 2.2 and 9.0 × 105 for linalool and 39 and 1.0 × 108 for citral. Behavior is bimodal antioxidant/pro-oxidant depending on the concentration. Calculations at the M05/6-311+g(2df,2p) level indicate that citral reacts selectively at the aldehyde C–H having activation enthalpy and energy respectively lower by 1.3 and 1.8 kcal/mol compared to the most activated allyl position. Their termination-enhancing antioxidant chemistry might be relevant in food preservation and could be exploited under appropriate settings.
Explaining the antioxidant activity of some common non-phenolic components of essential oils / Baschieri, Andrea; Ajvazi, Majlinda Daci; Tonfack, Judith Laure Folifack; Valgimigli, Luca; Amorati, Riccardo. - In: FOOD CHEMISTRY. - ISSN 0308-8146. - STAMPA. - 232:(2017), pp. 656-663. [10.1016/j.foodchem.2017.04.036]
Explaining the antioxidant activity of some common non-phenolic components of essential oils
BASCHIERI, ANDREA;VALGIMIGLI, LUCA;AMORATI, RICCARDO
2017
Abstract
Limonene, linalool and citral are common non-phenolic terpenoid components of essential oils, with attributed controversial antioxidant properties. The kinetics of their antioxidant activity was investigated using the inhibited autoxidation of a standard model substrate. Results indicate that antioxidant behavior of limonene, linalool and citral occurs by co-oxidation with the substrate, due to very fast self-termination and cross-termination of the oxidative chain. Rate constants kp and 2kt, (M−1 s−1) at 30 °C were 4.5 and 3.5 × 106 for limonene, 2.2 and 9.0 × 105 for linalool and 39 and 1.0 × 108 for citral. Behavior is bimodal antioxidant/pro-oxidant depending on the concentration. Calculations at the M05/6-311+g(2df,2p) level indicate that citral reacts selectively at the aldehyde C–H having activation enthalpy and energy respectively lower by 1.3 and 1.8 kcal/mol compared to the most activated allyl position. Their termination-enhancing antioxidant chemistry might be relevant in food preservation and could be exploited under appropriate settings.File | Dimensione | Formato | |
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