A beta-2-methoxyethyl alpha-3-[tris(trimethylsiloxy)silyl]propyl itaconate (1) was synthesized successfully as a novel amphiphilic itaconate monomer, and its radical homopolymerization and copolymerization with styrene (St) were investigated. The polymerization rate (Rp) is expressed with Rp = k[1](2.73)[AIBN](0.51). Overall activation energy in the radical homopolymerization was determined to be 52.9 kJ/mol. The 1 copolymerized with St in bulk in a highly alternating tendency. The Q, e values of the 1 were obtained to be 1.05 and 0.69, respectively, and the 1 was found to be a conjugative and electron-accepting monomer. Membranes containing the 1 unit, prepared by the copolymerization of 1 with N-vinylpyrrolidone (NVP) and by the terpolymerization of 1, NVP, and 2-hydroxyethyl methacrylate, showed higher oxygen permeability than corresponding ones without the 1 unit, and also they have better transparency than membranes containing 3-[tris(trimethylsiloxy)silyl]propyl methacrylate unit.