Stability of Apigeninidin and Its Methoxylated Derivatives in the Presence of Sulfites

3-Deoxyanthocyanin pigments are more stable than anthocyanins and show promising bioactive properties. However, little is known about their stability in the presence of food additives such as sulfites. This work investigates the stability of apigeninidin and its derivatives in the presence of sulfites. Pigment (apigeninidin, 5-mono-, and 5,7-dimethoxyapigeninidin) stability at pH 1.8, 3.0, and 5.0, in the presence of sodium metabisulfite (molar ratio similar to 1:40, pigment/SO2) was monitored over 21 days at room temperature. The structure of sulfite complexation products was monitored using HPLC-MS and NMR spectroscopy. All pigments were significantly bleached within 30 min in the presence of sulfites; the bleaching effect was more severe at pH 5.0 and 3.0 compared to pH 1.8. Apigeninidin was more resistant to bleaching than its methoxylated derivatives. However, all pigments regained some or all of the bleached color within 14-21 days at pH 3.0 and 1.8 in the presence of sulfites, indicating equilibrium favored flavylium cation at these pH values. Formation of colorless sulfonates via bisulfite ion addition at C-4 was responsible for the bleaching effect. Both structure and pH significantly affected stability of 3-deoxyanthocyanidins in the presence of sulfites. The pigments may have potential applications in low pH systems containing sulfites.