+)-/ra».i-Dihydroquercetin (taxifolin, 1) equilibrates with approximately 10% of its less stable (+)-«j diastereomer (epitaxifolin, 2) in hot aqueous or alcoholic solution by C-2 epimerization. The reaction is postulated to proceed through an optically active quinone methide formed by heterocyclic ring opening. Racemization and isomerization to alphitonin (2benzy 1-2,3' ,4,4' ,6-pentahydroxy-3 -coumaranone, 3) at elevated temperatures or with acid/base catalysts are attributable to slow deprotonation at C-3 and formation of an achiral ct-diketone intermediate. Dibasic sodium phosphate converts dihydroquercetin to the dihydrate of a hemisodium salt.
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