Coals and terrigenous sediments with suberinite dominant in organic macerals have been reported to generate certain quantities of low mature and high waxy oils. Evolution and mechanism of the generation, however, is not well constrained due to difficult separation and enrichment of the suberinite from geological samples. This issue was addressed in this paper, by using periderm cork tissues of modern angiosperm Quercus Suberus—a bio-precursor of the suberinite--in bacterial degradation and hydrous thermal simulation experiments. It is showed that the suberin has a multi-stage hydrocarbon generation history. Hydrocarbon generated in bacterial degradation is mainly gas, while is mainly oil in thermal simulation. The oil is greater in amount and generally has two generation peaks, corresponding to VRo at 0.35-0.5% and 0.8-1.1% respectively. The early-generated oil is predominated by oxygenated gum compounds, while the late-generated oil is mainly C12+ high waxy. These features are due to the lipid nature of the suberin. Chemical composition, structure and thermal stability heterogeneity of molecules in the suberin is fundamentally responsible for the multi-stage thermal degradation and hydrocarbon generation.