Intelligent Biopolymer-Based Films for Food Quality Monitoring

pH-responsive indicator films for intelligent food packaging applications are based on the embedding of a natural or synthetic dye in a polymeric substrate, preferably biobased and biodegradable. Although natural colorants like anthocyanins were extensively investigated in this respect, nature-inspired synthetic flavylium compounds could represent an alternative based on their higher stability. In this work, five novel synthetic 4'-aminoflavylium derivatives with different substitution patterns in the benzopyrylium core (compounds <b>1</b>-<b>5</b>) were synthesized and characterized. Polyvinyl alcohol (PVA), as well as chitosan-PVA and chitosan-starch blends, were used to prepare pH-responsive indicator films having inserted each of the synthesized flavylium dyes or a natural onion peel extract. The PVA films with compounds <b>1</b> and <b>3</b>, and the PVA-chitosan film with compound <b>1,</b> exhibited antioxidant activity, highlighting their potential for active packaging applications. All indicator films showed pH responsiveness in the range of 2 to 12 and were subsequently tested in contact with the packaging atmosphere or in direct contact with pork and fish meat, at different temperatures (4 °C, 20 °C, and 40 °C) for 24 h to assess their colorimetric response to progressive spoilage. Although the differences were small, the films with the 7-hydroxy-4'-aminoflavylium derivative exhibited the earliest and most intense color change during storage of meat, starting from direct contact at 4 °C for 24 h, being able to identify the initial stages of meat spoilage, while the performance of the dihydroxy-substituted derivative was attenuated by incorporation in polymer matrices. This behavior was comparable to that of onion peel extract, but the synthetic flavylium derivative was more stable. The results can provide new opportunities for intelligent food packaging applications using biopolymer indicator films with 4'-aminoflavylium derivatives.