Ditocopheryl Sulfides and Disulfides: Synthesis and Antioxidant Profile. Issue 38 (5th June 2019)

• Record Type: Journal Article
• Authors: Viglianisi, Caterina; Vasa, Kristian; Tanini, Damiano; Capperucci, Antonella; Amorati, Riccardo; Valgimigli, Luca; Baschieri, Andrea; Menichetti, Stefano
• Is Part Of: Chemistry. Volume 25:Issue 38(2019)
• Page Start: 9108
• Page End: 9116
• Publication Date: 2019-06-05
• Subjects: antioxidant activity -- organic synthesis -- sulfur -- tocopherols -- vitamin E; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201901537
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Symmetrical ditocopheryl disulfides (Toc )2 S2 and symmetrical and unsymmetrical ditocopheryl sulfides (Toc )2 S were simply prepared under remarkably mild conditions with complete control of the regiochemistry by using δ‐, γ‐, and β‐tocopheryl‐ N ‐thiophthalimides (Toc‐NSPht ) as common starting materials. The roles of sulfur atom(s), H‐bond and aryl ring substitution pattern on the antioxidant profile of these new compounds, which were assembled by linking together two tocopheryl units, are also discussed. Abstract : Two tocopherols and one (or two) S atom(s) : An easy access to all combinations of dicopheryl sulfides and disulfides from the same starting materials and under very mild conditions is reported. The role of sulfur atom(s) on the chain‐breaking antioxidant activity profile of this sulfur derivatives of vitamin E is disclosed.