Cyclic Voltammetry and Computational Chemistry Studies on the Evaluation of the Redox Behavior of Parabens and other Analogues
Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
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Data(s) |
05/11/2013
05/11/2013
2012
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Resumo |
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. |
Identificador |
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, SAO PAULO, v. 23, n. 3, pp. 565-572, MAR, 2012 0103-5053 http://www.producao.usp.br/handle/BDPI/41812 10.1590/S0103-50532012000300025 |
Idioma(s) |
eng |
Publicador |
SOC BRASILEIRA QUIMICA SAO PAULO |
Relação |
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY |
Direitos |
closedAccess Copyright SOC BRASILEIRA QUIMICA |
Palavras-Chave | #PRESERVATIVES #ELECTROANALYSIS #COMPUTATIONAL CHEMISTRY #SUBSTITUENT PATTERN #PHENOLIC COMPOUNDS #DOPED DIAMOND ELECTRODE #ZETA VALENCE QUALITY #PHENOLIC ANTIOXIDANTS #PERTURBATION-THEORY #HARTREE-FOCK #BASIS-SETS #DENSITY #EFFICIENT #CHEMISTRY, MULTIDISCIPLINARY |
Tipo |
article original article publishedVersion |