A simple method to prepare unsymmetrical di- tri- and tetrasulfides

Polysulfide-1-oxides react with peroxyl radicals as quickly as hindered phenolic antioxidants and do so by a surprising concerted homolytic substitution

“…22 These compounds, synthesized as described by Harpp 23 and Stensaas, 24 respectively, are solids at ambient temperature and allow direct comparison with petivericin (BnS(O)SBn) and its corresponding disulfide (BnSSBn). The reactivity of di- tert -butyltrisulfide ( t -BuSSS t -Bu) 23 and its 1-oxide ( t -BuS(O)SS t -Bu) 25 – also synthesized as described by Harpp – were also explored. These derivatives lack the activated β C–H in the allyl and benzyl moieties found in the garlic- and petiveria-derived allicin and petivericin, respectively. …”

Determination of the Concentration of Diallyl Trisulfide in Rat Whole Blood Using Gas Chromatography with Electron-Capture Detection and Identification of Its Major Metabolite with Gas Chromatography Mass Spectrometry

“…DATS, an oil-soluble constituent of garlic, has the same biological activities and can be obtained by chemical synthesis. 8,9) A great deal of eŠort has been devoted to measuring the levels of some OSCs and metabolites in vivo. Lachmann et al 10) investigated the pharmacokinetics of the garlic constituents alliin, allicin, and vinyldithiine using 35 S labeling, but this could not distinguish between drug antetype and metabolites and was harmful to volunteers.…”

Applications of Synthetic Organic Tetrasulfides as H2S Donors

“…Both trisulfides and tetrasulfides are synthetically accessible by treating a desired thiol with sulfur dichloride (SCl 2 ) or sulfur monochloride (S 2 Cl 2 ), respectively. 22 We chose to focus on tetrasulfides due to their higher sulfane sulfur content, thus higher H 2 S releasing potential with respect to trisulfides. Treatment of the parent thiol with S 2 Cl 2 and pyridine in anhydrous solvent at −78 °C afforded the desired tetrasulfide in good to excellent yield with no required purification (Table 1).…”