Octanoic acid 2-hydroxymethyl-4-oxo-4//-pyran-5-yl ester (kojic acid 5-O-capryloate, 2), octanoic acid 4-oxo-2-(l-oxooctyloxymethyl)-4//-pyran-5-yl ester (kojic acid 5,7-di-O-dicapryloate, 3), and octanoic acid (5-hydroxy-4-oxo-4//-pyran-2-yl)-methyl ester (kojic acid 7-O-capryloate. 5) were prepared from 5-hydroxy-2-hydroxymethyl-4//-4-pyrone (kojic acid, 1) and caprylic acid. We also describe the synthesis of 11-aminoundecanoic acid (5-hydroxy-4-oxo-4//-pyran-2-yl)-methyl ester (6 ). In solution, the monoesters are non-competitive in hibitors of mushroom tyrosinase (EC 1.14.18.1) (2: IC50 = 107 jiM, 5: IC5 0 = 15 jam, 6 : IC50 = 20 [.im; cf. 1: IC50 = 45 [.im, mixed type inhibition). When tyrosinase is immobilized in a polyvinylalcohol membrane, 5 is a weaker inhibitor than 1 or 2.
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