Journal of the Brazilian Chemical Society
Print version ISSN 0103-5053
GIL, Eric de S. et al. Cyclic voltammetry and computational chemistry studies on the evaluation of the redox behavior of parabens and other analogues. J. Braz. Chem. Soc. [online]. 2012, vol.23, n.3, pp. 565-572. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532012000300025.
Parabens are antimicrobial preservatives widely used in pharmaceutical, cosmetic and food industries. The alkyl chain connected to the ester group defines some important physicochemical characteristics of these compounds, including the partition coefficient and redox properties. The voltammetric and computational analyses were carried out in order to evaluate the redox behavior of these compounds and other phenolic analogues. A strong correlation between chemical substituents inductive effects of parabens with redox potentials was observed. Using cyclic voltammetry and glassy carbon working electrode, only one irreversible anodic peak was observed around 0.8 V for methylparaben (MP), ethylparaben (EP), propylparaben (PP), butylparaben (BP), benzylparaben (BzP) and p-substituted phenolic analogues. The electrodonating inductive effect of alkyl groups was demonstrated by the anodic oxidation potential shift to lower values as the carbon number increases and, therefore the parabens (and other phenolic analogues) oxidation processes to the quinonoidic forms showed great dependence on the substituent pattern.
Keywords : preservatives; electroanalysis; computational chemistry; substituent pattern; phenolic compounds.