Abstract：
:Seven new antioxidants derived from natural or synthetic phenols have been designed as alternatives to BHT and BHA antioxidants. Influence of various substituents at the ortho, meta and para positions of the aromatic core of phenols on the bond dissociation enthalpy of the ArO-H bond was evaluated using a DFT method B3LYP/6-311++G(2d,2p)//B3LYP/6-311G(d,p). This prediction highlighted the ortho-propenyl group as the best substituent to decrease the bond dissociation enthalpy (BDE) value. The rate constants of hydrogen transfer from these phenols to DPPH radical in a non-polar and non-protic solvent have been measured and were found to be in agreement with the BDE calculations. For o-propenyl derivatives from 2-tert-butyl-4-methylphenol, BHA, creosol, isoeugenol and di-o-propenyl p-cresol, fewer radicals were trapped by a single phenol molecule, i.e. a lower stoichiometric number. Reaction mechanisms involving the evolution of the primary phenoxyl radical ArO are proposed to rationalise these effects.
journal_name
Food Chemjournal_title
Food chemistryauthors
Marteau C,Guitard R,Penverne C,Favier D,Nardello-Rataj V,Aubry JMdoi
10.1016/j.foodchem.2015.09.007subject
Has Abstractpub_date
2016-04-01 00:00:00pages
418-27eissn
0308-8146issn
1873-7072pii
S0308-8146(15)01350-3journal_volume
196pub_type
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