Adaptive chaos, a concept rooted in chaos theory, describes the dynamic and non-linear behaviour of biological systems that enables adaptability and resilience under fluctuating conditions. This study investigates the potential role of phytochemicals, specifically flavonoids, as chemical promoters of adaptive chaos in biological systems. Using mathematical and bioinformatics modelling, we analyzed 23 representative flavonoids to determine their ability to induce adaptive chaos through receptor-ligand interactions. Ordinary differential equations were employed to simulate binding dynamics and evaluate oscillatory patterns and entropy variations, providing insights into the chaotic properties of these interactions. Key findings highlight that flavonoids such as quercetin, catechin, epicatechin, kaempferol, and apigenin, exhibit distinct capacities to modulate chaotic dynamics, enhancing cellular flexibility and stability. Quercetin emerged as the most effective inducer of adaptive chaos, characterized by high entropy, fractal dimensions and Lyapunov exponents, indicating superior responsiveness to perturbations. Catechin and epicatechin demonstrated targeted effects, particularly in stabilizing mitochondrial oscillations and modulating immune system dynamics, while kaempferol and apigenin maintained moderate adaptability. Correlation analysis further linked flavonoid-induced adaptive chaos with their prevalence in scientific literature, supporting the translational relevance of these compounds in therapeutic applications. The results suggest that flavonoids act as hormetic agents that stabilize oscillatory dynamics, promoting homeostasis and resilience in pathological states such as inflammation and mitochondrial dysfunction. This study introduces a novel approach for integrating chaos theory into biochemical modelling, providing a framework for future investigations into the dynamic regulatory roles of phytochemicals in health recovery and disease management.