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Aiming to distinguish the nutritional and safety impacts on consumer’s health of prolonged frying with vegetable oils rich in monounsaturated fatty acids (MUFA), namely peanut oil (PO), canola oil (CO) and extra virgin olive oil (EVOO), a domestic deep-frying assay using fresh potatoes was implemented (175 °C, 8 h per day, up to 28 h). Based on a total polar compounds (TPC) degradation limit of 25%, PO and CO enabled 18–20 h of frying, while EVOO allowed significantly higher frying hours (> 28 h). Despite the non-significant variations in oxidized triglycerides contents observed through time, and loss of all major antioxidants during the first 8 to 12 h of frying, PO showed statistically higher amounts of conjugated dienes (27 at 20 h; against 19 in CO and 17 in EVOO) and CO of anisidine value (252 at 20 h; against 209 in PO and 100 in EVOO), indicative of different oxidation patters. This was corroborated with the analysis of major volatiles, with PO and CO being statistically richer in alkenals and alkadienals, respectively. Therefore, despite the MUFA predominance, differences in their unsaturation profile impact on the type and amount of degradations products formed under prolonged frying and consequently on consumer’s health. As to EVOO use for prolonged frying, despite its increased resistance to oxidation and lower risk of formation of unhealthy volatiles, it loses its pool of natural bioactive compounds in the first hours of frying. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s13197-018-3489-z) contains supplementary material, which is available to authorized users.