Add time:08/10/2019         Source:sciencedirect.com

The oxygen exchange reactions of kojic acid and γ-pyrone were carried out in aqueous neutral, acidic and basic solutions. The incorporation of 18O in kojic acid is similar to that of γ-pyrone and the incorporation into the ring oxygen was observed. The exchange reactions of pyromeconic acid, maltol, allo-maltol, 5-methoxykojic acid, 6-methylkojic acid and 6-hydroxymethylkojic acid also proceed in an alkaline medium. The results obtained show that the ring opening is sensitive to the position and nature of a substituent on the γ-pyrone ring. A compound, having an electron-withdrawing group at the 2 or 6-position of the γ-pyrone ring incorporated more 18O than a compound having an electron-releasing group. The mechanism of oxygen exchange reaction is discussed together with resonance effect of kojiate anion.

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