In the present investigation the ability of different phenolic compounds, either present or not in olive oil, to induce both apoptosis on tumour cells and H<sub>2</sub>O<sub>2</sub> accumulation in cell culture medium was assesed. Among the phenols studied we found that tyrosol (<I>p</I>-HPEA), homovanillic alcohol and protocatechuic, <I>o</I>-coumaric, vanillic, homovanillic, ferulic and syringic acids did not induce either apoptosis on HL60 cells or H<sub>2</sub>O<sub>2</sub> accumulation, while hydroxytyrosol (3,4-DHPEA), 3,4-dihydroxyphenylacetic acid (3,4-DHPA), 3,4-dihydroxy-hydrocinnamic acid (3,4-DHHC) and gallic acid induced both apoptosis and accumulation of H<sub>2</sub>O<sub>2</sub> in the culture medium which were significantly reduced by catalase. In contrast, the dialdehydic form of elenoic acid linked to hydroxytyrosol (3,4-DHPEA-EDA) and to tyrosol (<I>p</I>-DHPEA-EDA) induced high level of apoptosis not reduced by catalase. Finally, oleuropein exerted a weak pro-apoptotic effect not mediated by H<sub>2</sub>O<sub>2</sub> release. From these results it is evident that: (<I>I</I>) the cathecol moiety of phenols is necessary but not sufficient to induce apoptosis and H<sub>2</sub>O<sub>2</sub> accumulation; <I>(ii</I>) the 3,4-DHPEA metabolism may partially reduce its pro-apoptotic potential; <I>(iii</I>) the pro-apoptotic activity of 3,4-DHPEA-EDA and<I> p</I>-DHPEA-EDA is not mediated by H<sub>2</sub>O<sub>2</sub> releasing activity.