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Reaction of γ-Tocopherol with Hypochlorous Acid

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Lipids

Abstract

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 (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-γ-tocopherol, 3-chloro-γ-tocopheryl quinone and its ether dimer are new compounds.

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Acknowledgments

Thanks are due to Dr. K. Fisher for running the mass spectra, to Mrs. H. Stender for the NMR spectra, and to Dr. J. Brophy for helpful discussions.

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Authors and Affiliations

  1. School of Chemistry, University of New South Wales, Sydney, NSW, 2052, Australia

    Quyen Nguyen & Peter T. Southwell-Keely

  2. 157 Hopetoun Avenue, Vaucluse, NSW, 2030, Australia

    Peter T. Southwell-Keely

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  1. Quyen Nguyen
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  2. Peter T. Southwell-Keely
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Correspondence to Peter T. Southwell-Keely.

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Nguyen, Q., Southwell-Keely, P.T. Reaction of γ-Tocopherol with Hypochlorous Acid. Lipids 42, 171–178 (2007). https://doi.org/10.1007/s11745-006-3016-2

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  • DOI: https://doi.org/10.1007/s11745-006-3016-2

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