Synthesis, characterization and bioactivity evaluation of diallyl disulfide

Abstract

Diallyl disulfide was synthesized by phase transfer catalyst (PTC) during microwave irradiation. The effects of different factors, such as the power of microwave irradiation, the time of microwave irradiation, PTC reagents amount and the mole ratio of reactants, on the yield of product were investigated. The structure of diallyl disulfide was characterized by infrared spectra, mass spectra and ¹H nuclear magnetic resonance. The bioactivity of diallyl disulfide was evaluated by cell viability assay on HepG2 hepatoma cells. The results show that the optimal reaction conditions are as follows: tetrabutylammonium bromide (TBAB) selected as a PTC, the mass ratio of TBAB to sodium disulfide of 0.021:1, the power of irradiation of 195 W, the reaction time of 12 min, and the mole ratio of sodium disulfide to allyl chloride of 0.65:1. The yield of diallyl disulfide is 82.2%. The synthetical diallyl disulfide appears to be cytotoxic to HepG2 hepatoma cells in a dose-dependent manner.

Keywords

diallyl disulfide / microwave irradiation / phase transfer catalyst / bioactivity