KINETIC ESR STUDY ON THE REACTION OF VITAMIN-E RADICAL WITH VITAMIN-C AND ITS LIPOPHILIC DERIVATIVES IN CETYLTRIMETHYLAMMONIUM BROMIDE MICELLES

被引：40

作者：

LIU, ZL ^{[1
]}

HAN, ZX ^{[1
]}

YU, KC ^{[1
]}

ZHANG, YL ^{[1
]}

LIU, YC ^{[1
]}

机构：

[1] LANZHOU UNIV, DEPT CHEM, LANZHOU 730000, PEOPLES R CHINA

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1992年 / 5卷 / 01期

关键词：

D O I：

10.1002/poc.610050105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction between alpha-tocopheroxyl radical (VE) and ascorbic acid (VC) and its lipophilic derivatives ascorbyl-6-caprylate (VC-8), 6-laurate (VC-12) and 6-palmitate (VC-16) was studied by stopped-flow ESR spectroscopy in cetyltrimethylammonium bromide (CTAB) micelles. The second-order rate constants for the reaction were found to be 9.0, 3.0, 0.7 and 0.03 x 10(5) l mol-1 s-1 for VC, VC-8, VC-12 and VC-16, respectively, indicating a remarkable influence of the aliphatic side-chain on the reactivity. The lifetime of the reaction intermediate, ascorbate radical anion, was greatly enhanced by the lipophilic side-chain, being 0.4, 5 and 110 s for VC-8-., VC-12-. and VC-16-. respectively. Kinetic analysis shows that the inter- and intramicellar diffusion may be the rate-limiting steps for the reaction carried out in micelles.

引用

页码：33 / 38

页数：6

共 26 条

[1] THEORY OF KINETICS OF MICELLAR EQUILIBRIA AND QUANTITATIVE INTERPRETATION OF CHEMICAL RELAXATION STUDIES OF MICELLAR SOLUTIONS OF IONIC SURFACTANTS [J].

ANIANSSON, EAG ;

WALL, SN ;

ALMGREN, M ;

HOFFMANN, H ;

KIELMANN, I ;

ULBRICHT, W ;

ZANA, R ;

LANG, J ;

TONDRE, C .

JOURNAL OF PHYSICAL CHEMISTRY, 1976, 80 (09) :905-922

[2] C-13 CHEMICAL-SHIFTS OF LONG-CHAIN EPOXIDES, ALCOHOLS AND HYDROPEROXIDES [J].

BASCETTA, E ;

GUNSTONE, FD .

CHEMISTRY AND PHYSICS OF LIPIDS, 1985, 36 (03) :253-261

[3] MECHANISM OF DISPROPORTIONATION OF ASCORBATE RADICALS [J].

BIELSKI, BHJ ;

ALLEN, AO ;

SCHWARZ, HA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (12) :3516-3518

[4] SIMPLE METHOD FOR QUANTIFYING THE DISTRIBUTION OF ORGANIC SUBSTRATES BETWEEN THE MICELLAR AND AQUEOUS PHASES OF SODIUM DODECYL-SULFATE SOLUTION [J].

BURKEY, TJ ;

GRILLER, D ;

LINDSAY, DA ;

SCAIANO, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (07) :1983-1985

[5] MICELLAR SYSTEMS AS DEVICES FOR ENHANCING THE LIFETIMES AND CONCENTRATIONS OF FREE-RADICALS [J].

BURKEY, TJ ;

GRILLER, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (01) :246-249

[6] IS VITAMIN-E THE ONLY LIPID-SOLUBLE, CHAIN-BREAKING ANTIOXIDANT IN HUMAN-BLOOD PLASMA AND ERYTHROCYTE-MEMBRANES [J].

BURTON, GW ;

JOYCE, A ;

INGOLD, KU .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1983, 221 (01) :281-290

[7]

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

[8] INHIBITION-KINETICS OF CHAIN-BREAKING PHENOLIC ANTIOXIDANTS IN SDS MICELLES - EVIDENCE THAT INTERMICELLAR DIFFUSION RATES MAY BE RATE-LIMITING FOR HYDROPHOBIC INHIBITORS SUCH AS ALPHA-TOCOPHEROL [J].

CASTLE, L ;

PERKINS, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6381-6382

[9]

Halliwell B., 1985, FREE RADICAL BIO MED, V1, P331, DOI 10.1016/0748-5514(85)90140-0

[10]

HAN ZX, 1989, THESIS LANZHOU U

← 1 2 3 →