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Ditocopheryl Sulfides and Disulfides: Synthesis and Antioxidant Profile
Caterina Viglianisi1, Kristian Vasa1, Damiano Tanini1
1Department of Chemistry "Ugo Schiff", University of Florence, Via Della Lastruccia 3-13, Sesto Fiorentino, Firenze, Italy.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 25, 2019
Summary
New tocopheryl compounds, ditocopheryl disulfides and sulfides, were synthesized using mild conditions. Their antioxidant properties were investigated, exploring the impact of sulfur atoms and structural variations.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Antioxidant Research
Background:
- Tocopherols (vitamin E) are known antioxidants.
- Developing novel antioxidant compounds is crucial for health and material science.
- Understanding structure-activity relationships of tocopheryl derivatives is important.
Purpose of the Study:
- To synthesize novel symmetrical and unsymmetrical ditocopheryl disulfides and sulfides.
- To investigate the antioxidant properties of these newly synthesized compounds.
- To elucidate the influence of sulfur linkage, hydrogen bonding, and aryl ring substitution on antioxidant activity.
Main Methods:
- Synthesis of tocopheryl-N-thiophthalimides (Toc-NSPht) as precursors.
- Mild reaction conditions for preparing ditocopheryl disulfides ((Toc)2S2) and sulfides ((Toc)2S).
- Regiochemical control during synthesis.
Main Results:
- Successful and simple preparation of symmetrical and unsymmetrical ditocopheryl disulfides and sulfides.
- Demonstrated complete regiochemical control using Toc-NSPht starting materials.
- Initial discussion on the antioxidant profiles influenced by sulfur atoms, H-bond, and aryl ring substitution.
Conclusions:
- Tocopheryl-N-thiophthalimides are versatile precursors for synthesizing ditocopheryl sulfur compounds.
- The synthesized compounds offer a new class of potential antioxidants.
- Further studies are warranted to fully characterize the antioxidant mechanisms and applications.
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