Carotenoids oxidation products are of interest for their possible biological activity. We produced and characterized a series of lycopene oxidative cleavage products by oxidizing lycopene. We synthesized apo-lycopenoids of various polyene chain lengths and terminal functions. Antioxidant activity of apo-lycopenoids was determined using a lipid peroxidation test mimicking oxidative stress in the gastro-intestinal tract. Results allowed us to establish structure-activity relationships of antioxidant protection of apo-lycopenoids in the gastro-intestinal tract. A long carbon chain and a carboxylic acid endgroup conferring an amphiphilic character to the molecule are favorable to the antioxidant activity of apo-lycopenoids.