Photolysis of NSAIDs. Part 3: Structural elucidation of photoproducts of tolmetin in methanol

Ming Thau Sheu, Jender Wu, Chih Jui Chen, Su Hui Chao, An-Bang Wu

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Photolysis of tolmetin in methanol produces eight photoproducts via a novel α-cleavage of a ketone, decarboxylation, and oxidation. A sample of 10 mM tolmetin in methanol was photo-irradiated with a Hanovia 200 W high-pressure quartz Hg lamp for four days. In total, eight photoproducts were observed from the HPLC chromatogram. Three major photoproducts were separated, and their structures were elucidated by spectroscopic methods. The structures of all photoproducts were further determined by LC-ESI-MS. A reaction scheme of tolmetin was proposed.

Original languageEnglish
Pages (from-to)8107-8109
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number43
DOIs
Publication statusPublished - Oct 18 2004

Fingerprint

Tolmetin
Photolysis
Non-Steroidal Anti-Inflammatory Agents
Methanol
Decarboxylation
Quartz
Ketones
Electric lamps
High Pressure Liquid Chromatography
Pressure
Oxidation

Keywords

  • LC-ESI-MS
  • Photoproducts
  • Tolmetin

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Photolysis of NSAIDs. Part 3 : Structural elucidation of photoproducts of tolmetin in methanol. / Sheu, Ming Thau; Wu, Jender; Chen, Chih Jui; Chao, Su Hui; Wu, An-Bang.

In: Tetrahedron Letters, Vol. 45, No. 43, 18.10.2004, p. 8107-8109.

Research output: Contribution to journalArticle

Sheu, Ming Thau ; Wu, Jender ; Chen, Chih Jui ; Chao, Su Hui ; Wu, An-Bang. / Photolysis of NSAIDs. Part 3 : Structural elucidation of photoproducts of tolmetin in methanol. In: Tetrahedron Letters. 2004 ; Vol. 45, No. 43. pp. 8107-8109.
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