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Literature DB >> 2761352

Reaction products of alpha-tocopherol with a free radical initiator, 2,2'-Azobis(2,4-dimethylvaleronitrile).

R Yamauchi¹, T Matsui, Y Satake, K Kato, Y Ueno.

Abstract

alpha-Tocopherol was reacted with an alkylperoxyl radical at 37 degrees C in ethanol. 2,2'-Azobis(2,4-dimethylvaleronitrile) was used to generate the alkylperoxyl radicals. The reaction products of alpha-tocopherol were isolated by reverse-phase and normal-phase high performance liquid chromatography, and their structures were characterized by infrared, ultraviolet, 1H and 13C nuclear magnetic resonances and mass spectrometry. They were 8aS-hydroperoxy-alpha-tocopherone, 8aR-hydroperoxy-alpha-tocopherone, a mixture of 7,8-epoxy-8aS-ethoxy-alpha-tocopherone and 7,8-epoxy-8aR-ethoxy-alpha-tocopherone, 8aS-(1R-cyano-1,3-dimethyl)butylperoxy-alpha-tocopherone+ ++, 8aS-(1S-cyano-1,3-dimethyl)butylperoxy-alpha-tocopherone+ ++, a mixture of 8aR-(1R-cyano-1,3-dimethyl)butylperoxy-alpha-tocopherone+ ++ and 8aR-(1S-cyano-1,3-dimethyl)butyl-peroxy-alpha-tocopherone, 4aS,5R-epoxy-8aR-ethoxy-alpha-tocopherone, 4aR,5S-epoxy-8aS-ethoxy-alpha-tocopherone, 4aS,5R-epoxy-8aS-ethoxy-alpha-tocopherone and 4aR,5S-epoxy-8aR-ethoxy-alpha-tocopherone.

Entities: Chemical

Mesh：

Substances：

Year: 1989 PMID： 2761352 DOI： 10.1007/BF02535235

Source DB: PubMed Journal: Lipids ISSN： 0024-4201 Impact factor: 1.880

12 in total

1. Dye-sensitized photooxidation of -tocopherol.

Authors: G W Grams; K Eskins; G E Inglett
Journal: J Am Chem Soc Date: 1972-02-09 Impact factor: 15.419

2. The oxidative dimerization of alpha-,beta-, gamma-, and delta-tocopherols.

Authors: J L Nilsson; G D Daves; K Folkers
Journal: Acta Chem Scand Date: 1968

3. Vitamin E oxidation with free radical initiators. Azobis-isobutyronitrile.

Authors: W A Skinner
Journal: Biochem Biophys Res Commun Date: 1964-04-22 Impact factor: 3.575

4. Microsomal lipid peroxidation.

Authors: J A Buege; S D Aust
Journal: Methods Enzymol Date: 1978 Impact factor: 1.600

5. Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C.

Authors: E Niki; T Saito; A Kawakami; Y Kamiya
Journal: J Biol Chem Date: 1984-04-10 Impact factor: 5.157

6. The antioxidant activity of alpha-tocopherol-bovine serum albumin complex in micellar and liposome autoxidations.

Authors: L R Barclay; A M Bailey; D Kong
Journal: J Biol Chem Date: 1985-12-15 Impact factor: 5.157

7. Radical scavenging reactions of alpha-tocopherol. II. The reaction with some alkyl radicals.

Authors: S Urano; S Yamanoi; Y Hattori; M Matsui
Journal: Lipids Date: 1977-01 Impact factor: 1.880

8. A radical scavenging reaction of alpha-tocopherol with methyl radical.

Authors: S Urano; M Matsuo
Journal: Lipids Date: 1976-05 Impact factor: 1.880

9. Solvent influence on model oxidations of alpha-tocopherol.

Authors: M Sumarno; E Atkinson; C Suarna; J K Saunders; E R Cole; P T Southwell-Keely
Journal: Biochim Biophys Acta Date: 1987-08-15

10. Oxidation of alpha-tocopherol in micelles and liposomes by the hydroxyl, perhydroxyl, and superoxide free radicals.

Authors: K Fukuzawa; J M Gebicki
Journal: Arch Biochem Biophys Date: 1983-10-01 Impact factor: 4.013

10 in total

Review 1. The chemistry and antioxidant properties of tocopherols and tocotrienols.

Authors: A Kamal-Eldin; L A Appelqvist
Journal: Lipids Date: 1996-07 Impact factor: 1.880

2. Reaction of alpha-tocopherol in heated bulk phase in the presence of methyl linoleate (13S)-hydroperoxide or methyl linoleate.

Authors: R Yamauchi; K Goto; K Kato
Journal: Lipids Date: 1998-01 Impact factor: 1.880

10. Formation of α-tocopherol hydroperoxide and α-tocopheroxyl radical: relevance for photooxidative stress in Arabidopsis.

Authors: Aditya Kumar; Ankush Prasad; Pavel Pospíšil
Journal: Sci Rep Date: 2020-11-12 Impact factor: 4.379

10 in total

Reaction products of alpha-tocopherol with a free radical initiator, 2,2'-Azobis(2,4-dimethylvaleronitrile).

1. Dye-sensitized photooxidation of -tocopherol.

2. The oxidative dimerization of alpha-,beta-, gamma-, and delta-tocopherols.

3. Vitamin E oxidation with free radical initiators. Azobis-isobutyronitrile.

4. Microsomal lipid peroxidation.

5. Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C.

6. The antioxidant activity of alpha-tocopherol-bovine serum albumin complex in micellar and liposome autoxidations.

7. Radical scavenging reactions of alpha-tocopherol. II. The reaction with some alkyl radicals.

8. A radical scavenging reaction of alpha-tocopherol with methyl radical.

9. Solvent influence on model oxidations of alpha-tocopherol.

10. Oxidation of alpha-tocopherol in micelles and liposomes by the hydroxyl, perhydroxyl, and superoxide free radicals.

Review 1. The chemistry and antioxidant properties of tocopherols and tocotrienols.

2. Reaction of alpha-tocopherol in heated bulk phase in the presence of methyl linoleate (13S)-hydroperoxide or methyl linoleate.

3. Oxidation products of cyanidin 3-O-beta-D-glucoside with a free radical initiator.

4. Reaction of alpha-tocopherol with alkyl and alkylperoxyl radicals of methyl linoleate.

5. Inhibition of 2,2'-azobis(2,4-dimethylvaleronitrile)-induced lipid peroxidation by sesaminols.

6. Antioxidant stoichiometry and the oxidative fate of vitamin E in peroxyl radical scavenging reactions.

7. Chemiluminescence detection of 8a-hydroperoxy-tocopherone in photooxidized alpha-tocopherol.

8. Oxidation of the α-tocopherol model compound 2,2,5,7,8-pentamethyl-6-chromanol in the presence of alcohols.

9. Iron-catalyzed reaction products of alpha-tocopherol with methyl 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoate.

10. Formation of α-tocopherol hydroperoxide and α-tocopheroxyl radical: relevance for photooxidative stress in Arabidopsis.