Preparation and Characterization of Urushiol Methylene Acetal Derivatives with Various Degrees of Unsaturation in Alkyl Side Chain

Abstract

Preparation of urushiol derivatives was carried out in response to the drug industry's increasing demand for new synthetic anticancer agents. Urushiol methylene acetal derivatives were synthesized in high yields by reaction of urushiol with methylene chloride under the catalytic action of NaOH. Four kinds of urushiol methylene acetal monomers were separated by silica-gel column and preparative HPLC, and their structures were elucidated by extensive spectroscopic methods, including 1D-NMR and 2D-NMR (1H, 13C-NMR, 1H-1HCOSY, HSQC, and HMBC) as well as TOF-MS. They were identified as 3-[pentadecyl] benzene methylene ether (compound 1), 3-[8′-pentadecatrienyl] benzene methylene ether (compound 2), 3-[8′,11′-pentadecatrienyl] benzene methylene ether (compound 3), and 3-[8′,11′,14′-pentadecatrienyl] benzene methylene ether (compound 4). This research provides a theoretical reference for exploration of these interesting and potentially bioactive compounds.