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Updated: Aug 18, 2026

A Generalized Method for Determining Free Soluble Phenolic Acid Composition and Antioxidant Capacity of Cereals and Legumes
Published on: June 10, 2022
Structure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic
Nikolaos Nenadis1, Hong-Yu Zhang, Maria Z Tsimidou
1Laboratory of Food Chemistry and Technology, School of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
Abstract:
Differences in the antioxidant activity of some biosynthetically related ferulic acid derivatives induced by the presence of characteristic groups (-COOH, -CHO, -CH(2)OH, -CH(3), and -COOC(2)H(5)) at the end of their carbon side chain were investigated using both experimental and computational methods. The relative order of the scavenging activity toward the DPPH radical derived from kinetic studies was isoeugenol approximately coniferyl alcohol >> ferulic acid approximately coniferyl aldehyde approximately ethyl ferulate. In bulk oil autoxidation (45 degrees C) the same order of activity was obtained. In the o/w emulsion autoxidation, lipophilicity of the phenols was the determining factor because the least polar compounds bearing -CH(3) and -COOC(2)H(5) were the most effective ones. The order of activity based on the O-H bond dissociation enthalpy (BDE) and ionization potential (IP) values, calculated by the density functional theory (DFT) method, was in accordance with the experimental radical scavenging order and with the electron-donating/withdrawing properties of the characteristic groups. Other molecular descriptors could not complement the experimental findings.
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