title: Reaction of gamma-tocopherol with hypochlorous acid.
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.
authors: School of Chemistry, University of New South Wales, Sydney, NSW, Australia.
authors: Quyen
authors: Q
authors: Nguyen
authors: Peter T
authors: PT
authors: Southwell-Keely
mesh_terms: D006997:Hypochlorous Acid / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D024504:gamma-Tocopherol / Q000737:chemistry*
chemical_list: D006997:Hypochlorous Acid; D024504:gamma-Tocopherol