title: Synthesis of eugenol esters by lipase-catalyzed reaction in solvent-free system.
abstract: Enzymatic esterification of eugenol is a matter of great scientific and technological interest due to the well-known drawbacks of the chemical-catalyzed route as well as the potential use of produced compounds as natural antimicrobials. This work reports the maximization of eugenil acetate production by esterification of eugenol and acetic anhydride in a solvent-free system using Novozym 435 as catalyst. The antimicrobial activity of eugenol and eugenil acetate was also determined. The operating conditions that maximized eugenil acetate production were 50 °C, eugenol to acetic anhydride of 1:3, 150 rpm, and 5.5 wt% of enzyme, with a conversion of 99 %. A kinetic study was performed to assess the influence of substrates molar ratio, enzyme concentration, and temperature on eugenil acetate yield. Results show that an excess of anhydride, low enzyme concentration (1 wt%), and 60 °C afforded nearly complete conversion after 6 h of reaction. The highest antimicrobial activity of eugenil acetate was observed against Acinetobacter sp. (48.66 mm) at concentration of 20 μL. Results indicate that the esterification of eugenol improved its antimicrobial properties. New experimental data on enzymatic esterification of eugenol and acetic anhydride are reported in this work, showing a promising perspective to overcome the inconvenient of the chemical-catalyzed route for obtaining antimicrobial natural compounds.
authors.affiliation: Department of Food Engineering, URI, Campus de Erechim, Av. Sete de Setembro, 1621, Erechim, Rio Grande do Sul 99700-000, Brazil.
authors.forename: V
authors.initials: V
authors.lastname: Chiaradia
authors.forename: N
authors.initials: N
authors.lastname: Paroul
authors.forename: R L
authors.initials: RL
authors.lastname: Cansian
authors.forename: C V
authors.initials: CV
authors.lastname: Júnior
authors.forename: M R
authors.initials: MR
authors.lastname: Detofol
authors.forename: L A
authors.initials: LA
authors.lastname: Lerin
authors.forename: J Vladimir
authors.initials: JV
authors.lastname: Oliveira
authors.forename: D
authors.initials: D
authors.lastname: Oliveira
mesh_terms: D000089:Acetic Anhydrides / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055162:Biocatalysis; D002175:Candida / Q000201:enzymology; D060326:Chemistry Techniques, Synthetic; D004800:Enzymes, Immobilized / Q000737:chemistry / Q000378:metabolism; D004951:Esterification; D004952:Esters; D005054:Eugenol / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D007700:Kinetics; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D013696:Temperature
chemical_list: D000089:Acetic Anhydrides; D000900:Anti-Bacterial Agents; D004800:Enzymes, Immobilized; D004952:Esters; C031800:acetic anhydride; D005054:Eugenol; D008049:Lipase