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This study explores the chemical composition of essential oils from two Serbian <i>Bupleurum</i> species (Apiaceae), <i>Bupleurum praealtum</i> L. and <i>Bupleurum affine</i> L., traditionally recognized in Chinese medicine for their therapeutic potential but less studied for their essential oils. Through GC-MS analysis, we identified 230 constituents, revealing distinct profiles between the species. Perillyl 2-methylbutanoate was identified in <i>B. affine</i> oil for the first time, confirmed using synthetic approaches and characterized by advanced spectroscopic techniques, including two-dimensional NMR and spin-simulation of ¹H NMR spectra. Additionally, new natural compounds, including tentatively identified 4-decyl acetate and 4-undecyl acetate, were discovered. The study also reports five stereoisomeric esters of tetradeca-5,7,9,11-tetraen-1-ol. These findings significantly contribute to the understanding of the phytochemical diversity within the genus <i>Bupleurum</i> and underscore potential differences in ecological adaptations or biosynthetic pathways among species.