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Per-2,3-acetyl-β-cyclodextrin is first synthesized by selective modification and used as core molecule for preparing a star-shaped macromolecular antioxidant (β-CD-DBHMP) via a two-step method. β-CD-DBHMP is characterized by 1H-NMR, MALDI-TOF MS, and TGA. The performance of β-CD-DBHMP as antioxidant for natural rubber is determined by OIT and accelerated thermal aging test, and its extraction resistance is also investigated. The results show that β-CD-DBHMP with a Mn of 4.03 × 103 g · mol−1 is successfully obtained, and it possesses high thermal stability with an initial weight loss temperature of 290 °C. Moreover, β-CD-DBHMP is superior to DBHMP for the stabilization of NR against thermal oxidation, and exhibits better extraction resistance. Its possible antioxidative mechanism is also discussed. [ABSTRACT FROM AUTHOR]