| Summary: | The interest in natural phenolic compounds has increased because of their attractive use especially as antioxidant and antimicrobial agents in foods. The large content in phenolic compounds of interest in <i>Santolina chamaecyparissus</i> L. (<i>S. chamaecyparissus</i>) makes this plant a target source that is worthy of note. In this work, new extraction technologies comprising ultrasound (UAE) and microwave (MAE) assisted extraction of the phenolic compounds in <i>S. chamaecyparissus</i> have been developed, optimized, and compared. Several extraction factors have been optimized based on a Box-Behnken design. Such optimized factors include the percentage of methanol in water (25–75%), the temperature (10–70 °C), the ultrasound amplitude (20–80%), the ultrasound cycle (0.2–1 s), the solvent pH (2–7) and the solvent-sample ratio (5/0.2–15/0.2 mL/g) with regard to UAE, while the percentage of methanol in water (50–100%), the temperature (50–100 °C), the pH (2–7) and the solvent-sample ratio (5/0.2–15/0.2 mL/g) were optimized for MAE. The solvent composition was the most influential parameter both on MAEs (64%) and UAEs (74%). The extraction optimum time was established as 15 min for MAE and 25 min for UAE. Five major phenolic compounds were detected and identified by Ultra-High-Performance Liquid Chromatography—Quadrupole Time of Flight—Mass Spectrometry (UHPLC-QToF-MS) in the extracts: chlorogenic acid, quercetin 3-<i>O</i>-galactoside, quercetin 3-<i>O</i>-glucoside, isoorientin, and cynarin. With the exception of chlorogenic acid, the other four compounds have been identified for the first time in <i>S. chamaecyparissus</i>. The findings have confirmed that MAE is a significantly more efficient extraction method than UAE to extract phenolic compounds from <i>S. chamaecyparissus.</i>
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