The Origin of Terpinen-4-ol in the Steam Distillates ofMelaleuca argentea, M. dissitifloraandM. linariifolia

The presence of terpinen-4-ol in the steam distillates from Melaleuca argentea, M. dissitiflora and M. linariifolia can be linked to high levels of (+)-sabinene and cis- and trans-sabinene hydrate in the leaf material. Incorporation of 18O into the terpinen-4-ol from steam distillates performed in H2 18O confirms the generation of the terpinen-4-yl carbocation intermediate from (+)-sabinene and cis- and trans-sabinene hydrate. This same mechanism is also operating during leaf aging.