Abstract: To address the challenge of easy oxidative decomposition of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP), two stable tobacco flavor materials, DDMP carbonate diester and DDMP carbonate triester, were synthesized using DDMP as the raw material. The structure of the target products was characterized using ¹H NMR, ¹³C NMR and HRMS techniques. Thermal gravimetric and pyrolysis analyses of DDMP carbonate diester and DDMP carbonate triester were performed using on-line pyrolysis gas chromatography/mass spectrometry (Py-GC-MS) technology. The results showed that: 1) Between 200-300 ℃, both DDMP carbonate diester and DDMP carbonate triester rapidly lost weight as a result of broken carbonate bond. 2) The main decomposition products of DDMP carbonate diester and DDMP carbonate triester were DDMP, furan and pyran compounds. 3) After adding DDMP carbonate diester and DDMP carbonate triester compounds to unflavored cigarettes, the transfer rates of DDMP in the mainstream smoke of the above cigarettes were 4.95% and 4.69%, respectively. In addition, the transfer rates of DDMP remained essentially the same within 90 days. This method could improve the flavor release stability of DDMP in cigarettes.