Fructose esters were synthesized from fructose and vinyl esters by transesterification catalyzed by lipase AK in anhydrous pyridine. The efficacy of ester synthesis was enhanced by increasing the length of carbon chain in the vinyl ester. Fructose monoesters and diesters were synthesized and their relative production ratio depended on the chain length of vinyl esters. Vinyl esters with chain length longer than C10 produced only monoacyl fructose which has an acyl moiety attached to C1 carbon of fructose. The monoacyl fructose composed of fatty acid with C10 or longer chains had a strong emulsifying activity on various hydrocarbons and oils.