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Caffeic acid (CA) as a strong antioxidant has lower solubility in nonpolar media, which limits its application in the food industry. To increase the lipophilicity of CA, 1-caffeoylglycerol (1-CG) was synthesized by lipasecatalyzed transesterification of alkyl caffeates in solvent-free system and its antioxidant capacity was investigated. Methyl caffeate was screened as the appropriate substrate from tested alkyl caffeates with a yield of 90.63%. Ethyl acetate was used for extracting 1-CG from enzymatic reactants and could be easily recycled. The produced 1-CG had 2.5-and 10-fold lower values of half maximal inhibitory concentration (IC 50 ) (10.86 and 3.99 μM) than butylated hydroxyanisole by 1,1-diphenyl-2-picrylhydrazyl radical scavenging and β-carotene-linoleic acid assays, respectively. Thus, 1-CG is an excellent antioxidant for application in the functional food industry. Using alkyl caffeates and glycerol as substrates to produce 1-CG catalyzed by immobilized lipase in a solvent-free system is a simple, selective, and safe bioprocess that can readily be achieved in the food industry, and the product 1-CG could be widely applied in food, nutraceutical, and biotechnological products.

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