Related Experiment Video
Updated: Jul 16, 2026

Controlled-release of Chlorine Dioxide in a Perforated Packaging System to Extend the Storage Life and Improve the Safety of Grape Tomatoes
Published on: April 7, 2017
Reaction of gamma-tocopherol with hypochlorous acid
Quyen Nguyen1, Peter T Southwell-Keely
1School of Chemistry, University of New South Wales, Sydney, NSW, Australia.
Abstract:
In addition to being a very good antioxidant, gamma-tocopherol is also an excellent electrophile trap. This is a study of the reactivity of gamma-tocopherol with hypochlorous acid/hypochlorite, a potential biological foe that is both an oxidant and an electrophile. Aqueous sodium hypochlorite (1.72 mmol; pH 7.4) was stirred with gamma-tocopherol (0.12 mmol) in hexane for 2 min at room temperature. The following products were isolated: gamma-tocopheryl quinone (0.6%), tocored (10%), 3-chloro-gamma-tocopheryl quinone (14%), an ether dimer of 3-chloro-gamma-tocopheryl quinone (0.4%), two isomers of 5-(5-gamma-tocopheryl)-gamma-tocopherol (3 and 2% respectively), 5-chloro-gamma-tocopherol (14%) and two chlorinated dimers (14 and 24% respectively) which were identified as diastereomers of (3R,10R)-11a-chloro-2,3,9,10-tetrahydro-3,5,6,10,12,13-hexamethyl-3,10-bis[(4R,8R)-4,8,12-trimethyltridecyl]-1H-pyrano(3,2a)-8H-pyrano(3,2g)-dibenzofuran-14(7aH)(14aH)-one. The chlorinated dimers, 5-chloro-gamma-tocopherol, 3-chloro-gamma-tocopheryl quinone and its ether dimer are new compounds.
Related Concept Videos
Preparation and Reactions of Thiols
Carboxylic Acids to Acid Chlorides
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Reactions at the Benzylic Position: Halogenation
Radical Substitution: Allylic Chlorination
Phase II Reactions: Glutathione Conjugation and Mercapturic Acid Formation
Several distinctive characteristics distinguish glutathione conjugation from other phase II...
