Aluminium ion-promoted radical-scavenging reaction of methylated hydroquinone derivatives

Ikuo Nakanishi, Kei Ohkubo, Yukihiro Ogawa, Ken Ichiro Matsumoto, Toshihiko Ozawa, Shunichi Fukuzumi

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The effect of the aluminium ion (Al3+) on the scavenging reaction of a 2,2-diphenyl-1-picrylhydrazyl radical (DPPH), as a reactivity model of reactive oxygen species, with hydroquinone (QH2) and its methylated derivatives (MenQH2, n = 1-4) was investigated using stopped-flow and electrochemical techniques in a hydroalcoholic medium. The second-order rate constants (k) for the DPPH-scavenging reaction of the hydroquinones increased with the increasing number of methyl substituents. Upon addition of Al3+, the k values significantly increased depending on the concentration of Al3+. Such an accelerating effect of Al3+ on the DPPH-scavenging rates of the hydroquinones results from the remarkable positive shift of the one-electron reduction potential (Ered) of DPPH in the presence of Al3+. These results demonstrate that Al3+, a strong Lewis acid, can act as a radical-scavenging promoter by stabilising the one-electron reduced species of the radical, although Al3+ is reported not only to act as a pro-oxidant but also to strongly interact with biomolecules, showing toxicities.

Original languageEnglish
Pages (from-to)7956-7961
Number of pages6
JournalOrganic and Biomolecular Chemistry
Issue number33
StatePublished - 2016

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© 2016 The Royal Society of Chemistry.


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