Tyrosinase-Catalyzed Hydroxylation of 4-Hexylresorcinol, an Antibrowning and Depigmenting Agent: A Kinetic Study.

Carmen Vanessa Ortiz-Ruiz, Jose Berna, Jose Neptuno Rodriguez-Lopez, Virginia Tomas, Francisco Garcia-Canovas

Index: J. Agric. Food Chem. 63 , 7032-40, (2015)

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Abstract

4-Hexylresorcinol (HR) is a compound used in the food and cosmetic industries as an antibrowning and lightening agent. Its use is mainly attributed to its inhibitory effect on the enzyme tyrosinase. However, the enzyme hydroxylates HR to an o-diphenol, which it then oxidizes to an o-quinone, which rapidly isomerizes to p-quinone. For tyrosinase to act in this way, the Eox form (oxy-tyrosinase) must be present in the reaction medium, which can be brought about by (a) hydrogen peroxide, (b) ascorbic acid, or (c) catalytic concentrations of o-diphenol and a reductant (NADH) to maintain it constant. This work demonstrates that HR is a substrate of tyrosinase and proposes a mechanism for its action. Its kinetic characterization provides a catalytic constant of 0.85 ± 0.04 s(-1) and a Michaelis constant of 60.31 ± 6.73 μM.