Effect of Alkyl Chain Length and Hydroxyl Substitution on the Antioxidant Activity of Gallic Acid Esters
Qi Chen, Shuaiwei Cui, Wenwen Zhang, Gang Dong, Baoshan Tang, Jinju Ma, Juan Xu, Jun Zhang, Lanxiang Liu
TL;DR
This study explores how modifying gallic acid with different ester groups affects its antioxidant activity and stability.
Contribution
The study reveals how alkyl chain length and hydroxyl substitution influence antioxidant performance of gallic acid esters.
Findings
Longer alkyl chains reduce DPPH radical scavenging activity of gallic acid esters.
Hydroxyl-substituted esters maintain high antioxidant activity and improve stability.
GA-C3 and hydroxyl-functionalized esters significantly prolong oxidation induction time in oil systems.
Abstract
Gallic acid (GA) exhibits excellent antioxidant properties but suffers from chemical instability due to its carboxyl group, which limits practical application. To address this, we designed and investigated 14 distinct ester derivatives of GA, which were categorized into two major groups based on their substituents: chain alkyl and hydroxyl-substituted alkyl groups. Systematic evaluation revealed a striking decline in the DPPH radical scavenging activity of alkyl esters with increasing carbon chain length, from 91.9% for GA-C3 to 55.6% for GA-C30. The hydroxyl-functionalized GA esters GA-EG, GA-GL, and GA-PT maintain high antioxidant activity (>90%) while improving applicability through carboxyl substitution. In the oil system, all derivatives significantly prolong the oxidation induction time, with GA-C3 exhibiting the highest performance by extending the induction time by 2.15 h.…
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Taxonomy
TopicsPhytochemicals and Antioxidant Activities · Free Radicals and Antioxidants · Edible Oils Quality and Analysis