Photoproducts of indomethacin

Pen Yuan Lin, Fu An Chen, An Bang Wu, Su Hui Chao, Yu Tang Peng, Vickie M H Lee, Chau Yang Chen

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

In a photochemical chamber, a sample of 27.9 mM indomethacin (IN) in methanol was exposed to a Philips 400-W UV lamp for 5 days in normal atmosphere. Four photoproducts were separated using high-performance liquid chromatography, and their structures were elucidated by various spectroscopic methods, including liquid chromatography–electrospray ionization–mass spectrometry. A reaction scheme of IN in methanol is proposed: The photochemical reaction routes occur mainly via esterification and decarboxylation, followed by oxidation with singlet oxygen to produce an aldehyde. A β-hydroxy-γ-lactone was also formed through a photochemical [2 + 2] cycloaddition, and its structure was confirmed by single-crystal X-ray diffraction.

Original languageEnglish
Pages (from-to)1777-1783
Number of pages7
JournalJournal of the Iranian Chemical Society
Volume13
Issue number10
DOIs
Publication statusPublished - Oct 1 2016

Keywords

  • Indomethacin
  • LC–ESI–MS
  • Photoproduct
  • β-Hydroxy-γ-lactone

ASJC Scopus subject areas

  • Chemistry(all)

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