Electrochemical and computational studies of phenolic antioxidants from cashew nut shell liquid

• Published in: Electrochimica acta Vol. 79; pp. 67 - 73
• Main Authors: Maia, Francisco J.N., Clemente, Claudenilson da S., Oliveira, Thiago M.B.F., Lomonaco, Diego, Oliveira, Túlio I.S., Almeida, Mayara O., de Lima-Neto, Pedro, Correia, Adriana N., Mazzeto, Selma E.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 30-09-2012; Elsevier
• Subjects: Antioxidants; Applied sciences; BHT; Cashew nut shell liquid; Coatings. Paints, varnishes and inks; Computation; Computational studies; Convergence; Derivatives; Electrochemical analysis; Electrochemistry; Exact sciences and technology; Liquids; Polymer industry, paints, wood; Shells; Voltammetry; Antioxidants; Cashew nut shell liquid; Electrochemistry; Computational studies; BHT; Frontier orbital; Computer simulation; Orbital interaction; Resorcinol derivatives; Theoretical study; Voltammetry; Vegetal by product; Raw materials; Antioxidant; Modeling; Cyclic voltammetry; Paint and varnish industry; Oxidation potential; Reaction mechanism; Phenols; Oxidation; Electrochemical reaction; Cashew nut; Square wave
• ISSN: 0013-4686; 1873-3859
• DOI: 10.1016/j.electacta.2012.06.086

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► Antioxidant capacity of CNSL compounds was evaluated by electrochemical methods. ► Cardol, cardanol and terc-butylated cardanol, showed better antioxidant activity than BHT. ► Electrochemical methods can be used in the study of antioxidant activity of phenolic compounds.
This work studied the antioxidant action of technical CNSL constituents, cardol (CD) and cardanol (CDN), and its synthetic derivative terc-butylated cardanol (terc-CDN) by electrochemical and computational methods. The electrochemical analyses were performed by square wave voltammetry and cyclic voltammetry in different pHs. The results showed that all compounds presented lower oxidation potentials when compared to the commercial product BHT (Epa=0.989V). Cardol presented the best values (Epa=0.665V), followed by terc-CDN (Epa=0.682V) and CDN (Epa=0.989V). The energy of the HOMO and LUMO orbitals, the Milliken charge and the analysis of molecular convergence obtained by computational methods confirmed the results obtained in electrochemical analysis proving that both techniques can be efficiently applied to this type of study.