biostudies-literatureQiu JJapan Society for the Promotion of Science5386-5397https://www.ebi.ac.uk/biostudies/studies/S-EPMC9393869biostudies-literatureUnknown126(32)1,2,4-Trioxolanes, known as secondary ozonides (SOZs), are key products of ozonolysis of biogenic terpenoids. Functionalized terpenoid-derived SOZs are readily taken up into atmospheric aerosols; however, their condensed-phase fates remain unknown. Here, we report the results of a time-dependent mass spectrometric investigation into the liquid-phase fates of C₁₀ and C₁₃ SOZs synthesized by ozonolysis of a C₁₀ monoterpene alcohol (α-terpineol) in water:acetone (1:1 = vol:vol) mixtures. Isomerization of Criegee intermediates and bimolecular reaction of Criegee intermediates with acetone produced C₁₀ and C₁₃ SOZs, respectively, which were detected as their Na⁺-adducts by positive-ion electrospray mass spectrometry. Use of CD<suThe journal of physical chemistry. AStability of Terpenoid-Derived Secondary Ozonides in Aqueous Organic Media.PMC939386919H01154Qiu JFujita MTonokura KEnami SfalseStability of Terpenoid-Derived Secondary Ozonides in Aqueous Organic Media.1,2,4-Trioxolanes, known as secondary ozonides (SOZs), are key products of ozonolysis of biogenic terpenoids. Functionalized terpenoid-derived SOZs are readily taken up into atmospheric aerosols; however, their condensed-phase fates remain unknown. Here, we report the results of a time-dependent mass spectrometric investigation into the liquid-phase fates of C₁₀ and C₁₃ SOZs synthesized by ozonolysis of a C₁₀ monoterpene alcohol (α-terpineol) in water:acetone (1:1 = vol:vol) mixtures. Isomerization of Criegee intermediates and bimolecular reaction of Criegee intermediates with acetone produced C₁₀ and C₁₃ SOZs, respectively, which were detected as their Na⁺-adducts by positive-ion electrospray mass spectrometry. Use of CD<su2022-01-01T00:00:00Z2022 Aug2025-04-22T01:45:50.762Z2025-04-05T20:07:13.527ZS-EPMC93938693592108610.1021/acs.jpca.2c04077