The biological activities of oleuropein (Ole) and its metabolites have been extensively documented and show a spectrum of highly interesting bioactivities, which demonstrates the potential of oleuropein for inclusion in food and beverages. In the present work, acetylated oleuropein (OleAc), a safe, biologically active semi-synthetic stable derivative of oleuropein, has been proposed as a facile alternative to make oleuropein more bioavailable and suitable for addition to fatty foods. Extra virgin olive oil (EVOO) has been proposed as a model of perishable food to evaluate the potential application of OleAc for the preparation of functional food and the impact of its formulation factors on the fragile nutritive components of EVOO. Both classical and ultrasound (US)-assisted enrichment procedures have been tested, and the evaluation of their effects on oil stability across time has been presented. Moreover, LC-MS analyses of hydrophilic extracts of target oils have been used to verify the stability of the acetylation of oleuropein over time after enrichment. Finally, a preliminary sensorial analysis has been performed in order to understand if this enrichment can result in oil taste modification. The present results are intended to provide preliminary support to meet the requirements of Novel Food status for OleAc.