Synthesis and evaluation of antioxidant and antifungal activities of novel ricinoleate-based lipoconjugates of phenolic acids

► Synthesis of four castor oil fatty acid-based lipoconjugates of phenolic acids. ► Lipoconjugates are evaluated for antioxidant and antimicrobial activities. ► Lipoconjugates possess good antioxidant and interesting antifungal properties. ► These could be used as potential lipophilic antioxidants for the storage of lipids. Syntheses of four castor oil fatty acid-based novel lipoconjugates of phenolic acids were carried out following Mitsunobu methodology. The lipid part consists of methyl ricinoleate and its saturated analogue, methyl-12-hydroxystearate and the phenolic moieties are ferulic and vanillic acid. Synthesised compounds are evaluated for antioxidant activity using three in vitro assays (DPPH radical scavenging assay, DSC studies for oxidative induction temperature of linoleic acid and autoxidation of linoleic acid in Tween 20 micellar medium) and compared with three widely used antioxidants in the food industry, BHT, α-tocopherol, and dodecyl gallate. Synthesised compounds are found to exhibit good antiradical activity. These compounds also exhibited very good antifungal activity against studied fungal strains. All these results suggested the applicability of the synthesised compounds as potent lipophilic antioxidants for combating oxidative stress.