Cyclopentanone was evaluated for spark-ignition fuel properties to determine potential as a bio-blendstock. Although key properties such as octane numbers and energy density are promising, when blended with commercial gasoline the oxidation stability was significantly reduced. Oxidation stability determination exposes fuel to mild oxidative conditions of 700 kPa oxygen followed by temperature increase to 100 degrees C, resulting in a final pressure of ~ 900 kPa. Oxygen consumption is determined by monitoring for decrease in pressure over time - the results evaluate potential for autoxidation during storage. An increase in oxidation rate from cyclopentanone was not anticipated given the relatively low reactivity of this compound. Detailed hydrocarbon analysis of blends before and after oxidation revealed cyclopentanone was not consumed, but alkenes were oxidized to a significantly higher degree with this compound present. Experiments with surrogate blends of isooctane, cyclopentanone, and linear isomers of hexene demonstrated that cyclopentanone catalyzes alkene oxidation to form epoxides under mild oxidative conditions. This unexpected behavior observed may have implications in low temperature combustion of alkenes when ketone fuels are present, as well as epoxidation chemistry. This study proposes a detailed mechanism for a catalytic cycle evaluated with quantum chemical calculations performed with density functional theory.