Curcuminoids, key bioactive compounds in turmeric, exhibit significant health benefits but suffer from poor bioavailability, limiting their therapeutic potential.Cyclodextrin (CD) encapsulation is a promising strategy to enhance bioavailability, yet studies primarily focus on curcumin (CUR), with limited exploration of other major curcuminoids such as demethoxycurcumin (DMC) and bisdemethoxycurcumin (BDMC).This study provides a comprehensive comparative anal. of the encapsulation behavior of CUR, DMC, and BDMC within β-cyclodextrin (β-CD) using a combination of phase solubility anal., NMR spectroscopy (1D-1H NMR, 2D-NOESY and DOSY), and mol. dynamics (MD) simulations. 1H NMR, NOESY spectra and diffusion studies revealed the strongest inclusion complex formation for BDMC, confirmed by phase stability constants (K).Mol. dynamics simulations further quantified the interaction strength through radial distribution functions (RDFs), close contact analyses, and hydrogen bonding patterns, highlighting the absence of -OCH3 groups in BDMC as a key factor for enhanced interaction.These findings provide crucial mechanistic insights into curcuminoids encapsulation, suggesting BDMC as a superior candidate for β-CD formulations, with implications for developing more effective nutraceutical and drug delivery systems.