Preparation and antioxidant activity of tyrosyl and homovanillyl ethers

► Tyrosyl and homovanillyl ethers were synthesized in high yields by a three-step procedure starting from tyrosol (Ty) and homovanillic alcohol (HMV). ► Homovanillyl series showed higher antioxidant activity than tyrosyl series after their evaluation by the Rancimat test in lipophilic food matrix and by the FRAP and ABTS assays in hydrophilic medium. ► Interestingly, homovanillyl alkyl ethers and homovanillic alcohol showed the best reducing power and radical scavenging activity of all evaluated compounds, even similar or slightly higher than that one previously reported for their ortho-diphenolic precursor, hydroxytyrosol. ► This batch of synthetic lipophilic compounds, derivatives of biologically active compounds such as tyrosol and homovanillic alcohol, provides interesting and potentially bioactive compounds.