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Reaction of γ‐Tocopherol with Hypochlorous Acid
Author(s) -
Nguyen Quyen,
SouthwellKeely Peter T.
Publication year - 2007
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-006-3016-2
Subject(s) - chemistry , hypochlorous acid , tocopherol , quinone , hypochlorite , medicinal chemistry , electrophile , dimer , organic chemistry , antioxidant , vitamin e , catalysis
In addition to being a very good antioxidant, γ‐tocopherol is also an excellent electrophile trap. This is a study of the reactivity of γ‐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 γ‐tocopherol (0.12 mmol) in hexane for 2 min at room temperature. The following products were isolated: γ‐tocopheryl quinone (0.6%), tocored (10%), 3‐chloro‐γ‐tocopheryl quinone (14%), an ether dimer of 3‐chloro‐γ‐tocopheryl quinone (0.4%), two isomers of 5‐(5‐γ‐tocopheryl)‐γ‐tocopherol (3 and 2% respectively), 5‐chloro‐γ‐tocopherol (14%) and two chlorinated dimers (14 and 24% respectively) which were identified as diastereomers of (3 R ,10 R )‐11a‐chloro‐2,3,9,10‐tetrahydro‐3,5,6,10,12,13‐hexamethyl‐3,10‐ bis [(4 R ,8 R )‐4,8,12‐trimethyltridecyl]‐1 H ‐pyrano(3,2a)‐8 H ‐pyrano(3,2g)‐dibenzofuran‐14(7a H )(14a H )‐one. The chlorinated dimers, 5‐chloro‐γ‐tocopherol, 3‐chloro‐γ‐tocopheryl quinone and its ether dimer are new compounds.