title: Synthesis and Characterization of a Novel Phenolic Lipid for Use as Potential Lipophilic Antioxidant and as a Prodrug of Butyric Acid.
abstract: Ferulic acid was modified to produce a novel phenolipid containing butyl chains. Ferulic acid was esterified with butanol to produce butyl ferulate which was further dihydroxylated followed by esterification with butyric anhydride to produce the phenolipid containing butyric acid. IR, NMR and MS techniques confirmed the structure of the synthesized structured lipophilic phenolic compound. The synthesized compound was tested for in vitro antioxidant and antimicrobial activities. The produced phenolipid showed moderate antioxidant activity in DPPH (2, 2-diphenyl-1-picrylhydrazyl) radical scavenging assay but in linoleic acid oxidation method, it exhibited good activity compared with the parent compound and the reference compounds. The prepared derivative could find applications as antioxidant in lipophilic systems and also as a potential prodrug of butyric acid. It also showed antibacterial effect against the four bacterial strains studied. The drug-likeness properties of the prepared molecule calculated were in the acceptable ranges according to Lipinski's rule of 5 and suggest that it has potential to cross the blood-brain barrier.
authors.affiliation: Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology.
authors.forename: Shiva Shanker
authors.initials: SS
authors.lastname: Kaki
authors.forename: Konda Reddy
authors.initials: KR
authors.lastname: Kunduru
authors.forename: Sanjit
authors.initials: S
authors.lastname: Kanjilal
authors.forename: Rachapudi Badari
authors.initials: RB
authors.lastname: Narayana Prasad
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001812:Blood-Brain Barrier; D000440:Butanols / Q000737:chemistry; D002087:Butyrates / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D003373:Coumaric Acids / Q000737:chemistry; D024881:Drug Resistance, Bacterial; D004951:Esterification; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011355:Prodrugs / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000975:Antioxidants; D000440:Butanols; D002087:Butyrates; D003373:Coumaric Acids; D062385:Hydroxybenzoates; D008055:Lipids; D011355:Prodrugs; C004999:ferulic acid; C017616:phenolic acid