Carotenoid oxidation products have various structures, among which epoxides and apo- or seco-carotenoids are the two main families. Although both these compound types are widely found in the natural world, the sensitivity of carotenoids to oxidation means they can also be an unwanted presence in in vitro assays. On the other hand, carotenoid oxidation products have also provided chemists with useful chemical tools for the structural identification of carotenoids, and in the natural world they are important biological mediators for plants and animals. In vitro, carotenoid oxidation products have been found to exert various effects which are either potentially beneficial or, on the contrary, detrimental to human health. However, to date, few carotenoid oxidation products have been found in humans. In order to isolate and characterize carotenoid oxidation products and identify their mechanism of formation, we set up two chemical oxidation systems. Lycopene was oxidized with potassium permanganate in a biphasic system to produce the fullest possible range of apo-lycopenals and some diapocarotene-dials. Biomimetic chemical systems of a heminic enzyme center were shown to oxidize lycopene and β-carotene into different families of molecules. Analysis by high-performance liquid chromatography coupled with a diode array-UV/vis detector and a mass spectrometry detector (HPLC-DAD-MS) was used to gain insight into the possible mechanisms of formation of the carotenoid oxidation products formed by these biomimetic systems.