Copper(II)-catalyzed oxidation of d-α-tocopherol by oxygen in aqueous solution

Yoshiko Itoh, Chie Miyamoto, Yoshikazu Matsushima, Shigenobu Matsumoto

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

α-Tocopherol (α-Toc) was solubilized in aqueous solutions using 13 solubilizing agents and the products of oxidation by oxygen in the presence and the absence of Cu(II) were analyzed by HPLC. In the presence of Cu(II), the oxidation was accelerated and 5-formyl-7,8-dimethyltocol and α- tocoquinone were the major oxidation products. Their yields greatly increased in the presence of Cu(II). The yields and the rates of formation of the products were dependent on the properties of solubilizing agents and other conditions as well as the presence of Cu(II) or other metal ions. It is suggested that slight changes in the structure of the solubilizing agents affect the course of the reaction.

Original languageEnglish
Pages (from-to)71-76
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume48
Issue number1
Publication statusPublished - 2000 Jan

Fingerprint

Tocopherols
Copper
Metals
High Pressure Liquid Chromatography
Ions
Oxygen
Oxidation
Metal ions
5-formyl-7,8-dimethyltocol

Keywords

  • α-tocoquinone
  • 5-formyl-7,8- dimethyltocol
  • Cu(II) catalysis
  • D-α-tocopherol
  • Oxidation
  • Sodium deoxycholate

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Copper(II)-catalyzed oxidation of d-α-tocopherol by oxygen in aqueous solution. / Itoh, Yoshiko; Miyamoto, Chie; Matsushima, Yoshikazu; Matsumoto, Shigenobu.

In: Chemical and Pharmaceutical Bulletin, Vol. 48, No. 1, 01.2000, p. 71-76.

Research output: Contribution to journalArticle

Itoh, Y, Miyamoto, C, Matsushima, Y & Matsumoto, S 2000, 'Copper(II)-catalyzed oxidation of d-α-tocopherol by oxygen in aqueous solution', Chemical and Pharmaceutical Bulletin, vol. 48, no. 1, pp. 71-76.
Itoh, Yoshiko ; Miyamoto, Chie ; Matsushima, Yoshikazu ; Matsumoto, Shigenobu. / Copper(II)-catalyzed oxidation of d-α-tocopherol by oxygen in aqueous solution. In: Chemical and Pharmaceutical Bulletin. 2000 ; Vol. 48, No. 1. pp. 71-76.
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