In oil-in-water emulsions, the physical location of antioxidants has been postulated to be one of the most important factors impacting activity. The purpose of this research was to examine how the esterification of various hydrocarbon chains (C4, C8, or C12) onto chlorogenic acid (CGA) influenced physical properties and antioxidant activity in menhaden oil-in-water emulsions. Both surface activity and partitioning of CGA and its hydrocarbon esters into the lipid phase of oil-in-water emulsions increased with increasing size of the hydrocarbon chain. When CGA and its esters were added to a menhaden oil-in-water emulsion at concentration that resulted in equal free radical scavenging activity, CGA, butyl CGA and octyl CGA had similar antioxidant activity while dodecyl CGA was ineffective. These results suggest that phenolic antioxidants conjugated with hydrocarbon chains are more highly associated with lipid emulsions droplets, but these changes in physical properties did not increase antioxidant activity.