Antioxidant properties of 4-vinyl derivatives of hydroxycinnamic acids

Petra Terpinc; Tomaž Polak; Nataša Segatin; Andrej Hanzlowsky; Nataša Poklar Ulrih; Helena Abramovič

doi:10.1016/j.foodchem.2011.02.077

Antioxidant properties of 4-vinyl derivatives of hydroxycinnamic acids

Food Chem. 2011 Sep 1;128(1):62-9. doi: 10.1016/j.foodchem.2011.02.077. Epub 2011 Feb 24.

Authors

Petra Terpinc¹, Tomaž Polak¹, Nataša Segatin¹, Andrej Hanzlowsky¹, Nataša Poklar Ulrih¹, Helena Abramovič²

Affiliations

¹ Biotechnical Faculty, University of Ljubljana, SI-1111 Ljubljana, Slovenia.
² Biotechnical Faculty, University of Ljubljana, SI-1111 Ljubljana, Slovenia. Electronic address: helena.abramovic@bf.uni-lj.si.

PMID: 25214330
DOI: 10.1016/j.foodchem.2011.02.077

Abstract

The compounds 4-vinylphenol (4-VP), 4-vinylguaiacol (4-VG), 4-vinylsyringol (4-VS) and 4-vinylcatechol (4-VC) were prepared by thermal decarboxylation of the corresponding hydroxycinnamic acids p-coumaric, ferulic, sinapic and caffeic acid, respectively. For confirmation of the synthesised products LC-MS followed by NMR analysis was used. To evaluate their antioxidant potential, their reducing power and efficiency in scavenging the alkylperoxyl radical generated in an emulsion system, the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and the superoxide anion radical (O2(-)) were determined. All tested 4-vinyl derivatives revealed weaker antioxidant activity in a homogeneous polar medium than the corresponding phenolic acids. In the emulsion system the activity for 4-vinyl derivatives was higher than was the activity of their corresponding phenolic acids, with 4-VG as the most active among the tested phenolic compounds.

Keywords: 4-Vinylcatechol; 4-Vinylguaiacol; 4-Vinylphenol; 4-Vinylsyringol; Antioxidant activity; Hydroxycinnamic acids.