Modeling the co-antioxidant behavior of monofunctional phenols. Applications to some relevant compounds

被引：69

作者：

Amorati, R ^{[1
]}

Ferroni, F ^{[1
]}

Pedulli, GF ^{[1
]}

Valgimigli, L ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40127 Bologna, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 25期

关键词：

D O I：

10.1021/jo0351825

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A study on the regeneration of a-tocopherol (vitamin E) by phenolic co-antioxidants in homogeneous hydrocarbon solution is reported. The behavior of some relevant phenols such as BHA, BHT, and trans-resveratrol appears to be nicely predicted by a model based on the knowledge of kinetic and thermochemical data concerning the various reactants. Despite its good reputation as an antioxidant, trans-resveratrol was found only moderately effective (k(inh) = 2.0 x 10(5) M-1 s(-1) in chlorobenzene at 303 K) and unable to recycle vitamin E.

引用

页码：9654 / 9658

页数：5

共 25 条

[1] Determination of antioxidant power of red and white wines by a new electrochemical method and its correlation with polyphenolic content [J].

Alonso, AM ;

Domínguez, C ;

Guillén, DA ;

Barroso, CG .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (11) :3112-3115

[2] A quantitative approach to the recycling of α-tocopherol by coantioxidants [J].

Amorati, R ;

Ferroni, F ;

Lucarini, M ;

Pedulli, GF ;

Valgimigli, L .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26) :9295-9303

[3] Absolute rate constants for the reaction of peroxyl radicals with cardanol derivatives [J].

Amorati, R ;

Pedulli, GF ;

Valgimigli, L ;

Attanasi, OA ;

Filippone, P ;

Fiorucci, C ;

Saladino, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (11) :2142-2146

[4] Determination of the substituent effect on the O-H bond dissociation enthalpies of phenolic antioxidants by the EPR radical equilibration technique [J].

Brigati, G ;

Lucarini, M ;

Mugnaini, V ;

Pedulli, GF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4828-4832

[5]

BURTON GW, 1986, ACCOUNTS CHEM RES, V19, P194, DOI 10.1021/ar00127a001

[6] AUTOXIDATION OF BIOLOGICAL MOLECULES .4. MAXIMIZING THE ANTIOXIDANT ACTIVITY OF PHENOLS [J].

BURTON, GW ;

DOBA, T ;

GABE, EJ ;

HUGHES, L ;

LEE, FL ;

PRASAD, L ;

INGOLD, KU .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7053-7065

[7] Density functional theory calculations for resveratrol [J].

Cao, H ;

Pan, XL ;

Li, C ;

Zhou, C ;

Deng, FY ;

Li, TH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (11) :1869-1871

[8] A METHOD FOR THE COMPARATIVE-ASSESSMENT OF ANTIOXIDANTS AS PEROXYL RADICAL SCAVENGERS [J].

DARLEYUSMAR, VM ;

HERSEY, A ;

GARLAND, LG .

BIOCHEMICAL PHARMACOLOGY, 1989, 38 (09) :1465-1469

[9]

Denisov E.T., 1974, LIQUID PHASE REACTIO

[10] MECHANISMS OF ACTION AND REACTIVITIES OF THE FREE-RADICALS OF INHIBITORS [J].

DENISOV, ET ;

KHUDYAKOV, IV .

CHEMICAL REVIEWS, 1987, 87 (06) :1313-1357

← 1 2 3 →