Dual role of phloretin in inhibiting 2-amino-3-methylimidazole[4,5-f]quinoline (IQ) formation and modulating flavor in a Maillard reaction model system.

IQ (2-amino-3-methylimidazo[4,5-f]quinoline), a heterocyclic aromatic amine (HAA) formed via the Maillard reaction in thermally processed foods, poses safety concerns. Polyphenols can inhibit HAAs and modulate flavor, but their dual efficacy and IQ-flavor interplay are limited. This study identified phloretin as the most potent IQ inhibitor (70.27 % reduction at 0.5 mmol/L) among the nine candidates in chemical model systems; it impacts precursors and key carbonyl intermediates and significantly suppresses pyrazine formation. Chemical calculations confirmed that hydroxyl/carbonyl oxygens and aromatic rings are potential active sites. The correlation of the precursor and intermediate products demonstrated that the distinctive acyclic carbon bridge structure of phloretin enables multiavenue inhibition by reducing precursor reactivity and critically scavenging essential carbonyl compounds, thereby blocking synthetic pathways and reducing IQ/pyrazine yields. This research reveals the structural basis for the synergistic coregulation of safety and flavor by phenolics during the Maillard reaction, providing a new strategy for developing dual-function food additives for hazard mitigation and flavor preservation.

• Publication year

  2025

• Venue

  Food Chemistry

• Publication date

  2025-11-30

• Fields of study

  Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.1016/j.foodchem.2025.147287PMID 41344246
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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