Thermo-Oxidative Decomposition of Lovage (Levisticum officinale) and Davana (Artemisia pallens) Essential Oils under Simulated Tobacco Heating Product Conditions

Abstract

Summary The thermo-oxidative decomposition of lovage (Levisticum officinale) and davana (Artemisia pallens) essential oils has been studied by pyrolysis-gas chromatography/mass spectrometry in 9% oxygen and 91% nitrogen atmosphere at 300 °C to simulate low-temperature tobacco heating conditions. Both lovage and davana oils contain numerous chemical substances; the main components of both oils are various oxygen-containing compounds. Isobenzofuranones are the most important constituents of lovage oil, and their relative intensity changed significantly during oxidative pyrolysis. (Z)-ligustilide underwent two kinds of decomposition reactions: an aromatization reaction resulting in the formation of butylidenephthalide and the scission of the lactone ring with the elimination of carbon dioxide or carbon monoxide. Davanone is the main component of davana oil, which did not decompose considerably during low-temperature oxidative pyrolysis. However, the relative yield of the second most intensive component, bicyclogermacrene, reduced markedly due to bond rearrangement reactions. Davana ether underwent oxidation reactions leading to the formation of various furanic compounds. The changes in the composition of both essential oils could be interpreted in terms of bond splitting, intramolecular rearrangement mechanisms and oxidation reactions of several constituents during low-temperature oxidative pyrolysis. The applied thermo-oxidative method was found to be suitable to study the stability of the essential oils and monitor the decomposition products under simulated tobacco heating conditions. In spite of the complicated composition of the essential oils, no evidence for interaction between the oil components was found. [Beitr. Tabakforsch. Int. 29 (2020) 27–43]