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The electrochemistry of aqueous solutions of 4-methoxy-1,2-benzoquinone
Journal article   Peer reviewed

The electrochemistry of aqueous solutions of 4-methoxy-1,2-benzoquinone

S.I. Bailey, I.M. Ritchie and H-G Zhang
Bioelectrochemistry and Bioenergetics, Vol.19(3), pp.521-531
1988
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Abstract

Using cyclic voltammetry, the electrochemistry of aqueous solutions of 4-methoxy-1,2-benzoquinone was investigated over the pH range 0–8. From the variation of half-wave potential with pH, it was inferred that the quinone was reduced to the hydroquinone; no acid-base reactions involving either the quinone or hydroquinone were observed. At low pH ( < 3), the cyclic voltammogram of the benzoquinone changed rapidly to a second pair of peaks at lower potentials. These were shown to be due to 2-hydroxy-1,4-benzoquinone, formed by hydrolysis of the original compound. The other hydrolysis product, methanol, was detected chromatographically. The hydrolysis reaction was shown to be first order both with respect to the 1,2-benzoquinone and protons. At pH 6 and above, 4-methoxy-1,2-benzoquinone showed a second type of decomposition whose rate was approximately first order in hydroxide ion. Using electrochemical and spectroscopic measurements, it was also demonstrated that 4-methoxy-1,2-benzoquinone was formed during the tyrosinase-catalysed oxidation of 4-methoxyphenol. This confirms that this quinone could be involved in the melanocytoxic action of 4-methoxyphenol.

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Citation topics
1 Clinical & Life Sciences
1.219 Cancer Drugs
1.219.1527 Naphthoquinone Derivatives
Web Of Science research areas
Biochemistry & Molecular Biology
Biophysics
ESI research areas
Biology & Biochemistry
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