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Increasing interest has been shown in phenolic compounds for enhancing food quality, but their hydrophilicity restricts application in lipophilic systems. Therefore, in this study, twelve hydroxycinnamates derivatives (alkyl and steryl esters of sinapic acid (SA), caffeic acid (CA), and ferulic acid [FA]) were synthesised and evaluated for antioxidant and cytotoxic characteristics. CA esters had the highest radical scavenging activity (RSA) analysed by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assays. Values of inhibitory concentration (IC50) of synthesised compounds were related to their structure and lipophilicity. The effect of these hydroxycinnamic acid esters on the antioxidant potential of real samples (rapeseed oil, margarine and mayonnaise) was estimated. None of the investigated derivatives significantly affected the viability of the model intestinal cells Caco2, while the octyl esters demonstrated a toxic effect at low concentrations. The synthesised esters exerted cytotoxic and anti-proliferative effects against transformed cell lines (HeLa and A549). Octyl esters were potent anticancer compounds on two human cancer cell lines. The synthesised phenolipids, as valuable and safe antioxidant additives, can find broader applications in the production of fat-based products to prevent oxidation processes, extend their shelf life and improve quality. [ABSTRACT FROM AUTHOR]