Chapter 12. Phenols as Antioxidants

  1. Zvi Rappoport
  1. L. Ross C. Barclay and
  2. Melinda R. Vinqvist

Published Online: 7 OCT 2003

DOI: 10.1002/0470857277.ch12



How to Cite

Barclay, L. R. C. and Vinqvist, M. R. (2003) Phenols as Antioxidants, in Phenols (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470857277.ch12

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Department of Chemistry, Mount Allison University, Sackville, New Brunswick, Canada, E4L 1G8. Fax: (506) 364-2313

Publication History

  1. Published Online: 7 OCT 2003
  2. Published Print: 22 JUL 2003

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471497370

Online ISBN: 9780470857274



This chapter contains sections titled:

  • Introduction

  • Kinetics and Mechanism

    • Autoxidation

    • Inhibition by Phenols

      • Antioxidant Activity and Stoichiometric Factor—H-atom Transfer and Electron Transfer Mechanisms

      • Reaction Products of Antioxidants: α-Toc

  • Efficiencies of Phenolic Antioxidants

    • Some Experimental Methods

      • Reaction of Phenolic Antioxidants with Peroxyl Radicals

        • Inhibited Oxygen Uptake (IOU) Measurement Techniques

        • Product Studies—Hydroperoxide Products

      • Reaction of Phenolic Antioxidants with Other Radical Sites

      • Overall Assessment of Strategies to Determine Antioxidant Activities

    • Structural Effects on Efficiencies of Antioxidants

      • Monohydroxy Phenols: Substituent Effects

      • Dihydroxy Phenols: Catechols and 1,4-hydroquinones—Intramolecular Hydrogen Bonding Revisited

    • Media Effects

      • Solvent Effects

        • Solvent Interactions with the Attacking Radicals

        • Solvent Interactions with Phenolic Antioxidants—Effects on Antioxidant Mechanisms

      • Antioxidants in Heterogeneous Systems: Lipid Peroxidation and Inhibition in Micelles and Lipid Membranes

        • Monohydroxy Phenols. Factors Controlling Antioxidant Activities in Membranes. The Unique Behavior of α-Toc

        • Di- and Polyhydroxy Phenols in Membranes. Ubiquinols and Flavonoids

  • Chemical Calculations on Phenols

    • Introduction

    • Application to Antioxidants

      • Antioxidant Mechanisms by Phenols: Hydrogen Atom Transfer (HAT) and Single Electron Transfer (SET)

      • Calculations of Substituent Effects for Monophenols

      • Calculations of More Complex Polyhydroxy Phenols

  • Future Prospects for Antioxidants

  • References