Synthesis and mass spectrometry of new compounds related to the tocopherols and plastoquinones

Seven new isomers of α-tocopherol acetate have been synthesized from di- and trimethylated phenols. The compounds synthesized are: 2,5,6,7-tetramethyl-8-acetoxy-2-(4′,8′,12′-trimethyltridecyl) chroman (“ortho tocopherol acetate”), 7, and the six possible structural isomers of dimethylphytyl-1-methoxy-4-acetoxy-benzene, 12, 13, 14, 15, 18, and 19. Upon mass spectral determination, the seven synthetic compounds and natural α-tocopherol acetate produced the same fragment ions, the only differences in the spectra being in the relative intensities of some of the fragments.