We investigated the quantitative structure-activity relationships between hemolytic activity (log 1/H-50) or in vivo mouse intraperitoneal (ip) LD50 using reported data for alpha,beta-unsaturated carbonyl compounds such as (meth) acrylate monomers and their C-13-NMR beta-carbon chemical shift (d). The log 1/H-50 value for methacrylates was linearly correlated with the delta C-beta value. That for (meth) acrylates was linearly correlated with log P, an index of lipophilicity. The ipLD(50) for (meth) acrylates was linearly correlated with delta C-beta but not with log P. For (meth) acrylates, the delta C-beta value, which is dependent on the p-electron density on the beta-carbon, was linearly correlated with PM3-based theoretical parameters (chemical hardness, eta; electronegativity, chi; electrophilicity, omega), whereas log P was linearly correlated with heat of formation (HF). Also, the interaction between (meth) acrylates and DPPC liposomes in cell membrane molecular models was investigated using H-1-NMR spectroscopy and differential scanning calorimetry (DSC). The log 1/H-50 value was related to the difference in chemical shift (Delta delta Ha) (Ha: H (trans) attached to the beta-carbon) between the free monomer and the DPPC liposome-bound monomer. Monomer-induced DSC phase transition properties were related to HF for monomers. NMR chemical shifts may represent a valuable parameter for investigating the biological mechanisms of action of (meth)acrylates.