Biomimetic synthesis and antioxidant evaluation of 3,4-DHPEA-EDA [2-(3,4-hydroxyphenyl) ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate]

• We synthesise 3,4-DHPEA-EDA starting from natural demethyloleuropein.
• Our biomimetic route exploited a low toxic Lewis acid hydrolysis followed by thermal decarboxylation.
• The stereochemistry of decarboxylation step was evaluated by NMR analysis of the deuterated analogue.
• We evaluated and compared the antioxidant capacity of 3,4-DHPEA-EDA to the others 3,4-DHPEA derivatives of VOO.

Phenolic compounds present in extra virgin olive oil have attracted considerable recent attention. Many of them, show specific anti-inflammatory and anti-tumor activities. In this work we describe the biomimetic synthesis of 3,4-DHPEA-EDA [2-(3,4-hydroxyphenyl) ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate], starting from natural demethyloleuropein present in olive tissues. A comparison between 3,4-DHPEA-EDA (6) and oleuropein (1), oleuropein aglycone (4) and hydroxytyrosol ORACFL values was undertaken.