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 journalArticle

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

Fingerprint

Indomethacin
Methanol
Ultraviolet lamps
Singlet Oxygen
Cycloaddition
Photochemical reactions
Esterification
High performance liquid chromatography
Lactones
Aldehydes
Spectrometry
Single crystals
X ray diffraction
Oxidation
Liquids
Decarboxylation

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Lin, P. Y., Chen, F. A., Wu, A. B., Chao, S. H., Peng, Y. T., Lee, V. M. H., & Chen, C. Y. (2016). Photoproducts of indomethacin. Journal of the Iranian Chemical Society, 13(10), 1777-1783. https://doi.org/10.1007/s13738-016-0895-x

Photoproducts of indomethacin. / Lin, Pen Yuan; Chen, Fu An; Wu, An Bang; Chao, Su Hui; Peng, Yu Tang; Lee, Vickie M H; Chen, Chau Yang.

In: Journal of the Iranian Chemical Society, Vol. 13, No. 10, 01.10.2016, p. 1777-1783.

Research output: Contribution to journalArticle

Lin, PY, Chen, FA, Wu, AB, Chao, SH, Peng, YT, Lee, VMH & Chen, CY 2016, 'Photoproducts of indomethacin', Journal of the Iranian Chemical Society, vol. 13, no. 10, pp. 1777-1783. https://doi.org/10.1007/s13738-016-0895-x
Lin PY, Chen FA, Wu AB, Chao SH, Peng YT, Lee VMH et al. Photoproducts of indomethacin. Journal of the Iranian Chemical Society. 2016 Oct 1;13(10):1777-1783. https://doi.org/10.1007/s13738-016-0895-x
Lin, Pen Yuan ; Chen, Fu An ; Wu, An Bang ; Chao, Su Hui ; Peng, Yu Tang ; Lee, Vickie M H ; Chen, Chau Yang. / Photoproducts of indomethacin. In: Journal of the Iranian Chemical Society. 2016 ; Vol. 13, No. 10. pp. 1777-1783.
@article{c5c030ef02434f0888d99e739826907c,
title = "Photoproducts of indomethacin",
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.",
keywords = "Indomethacin, LC–ESI–MS, Photoproduct, β-Hydroxy-γ-lactone",
author = "Lin, {Pen Yuan} and Chen, {Fu An} and Wu, {An Bang} and Chao, {Su Hui} and Peng, {Yu Tang} and Lee, {Vickie M H} and Chen, {Chau Yang}",
year = "2016",
month = "10",
day = "1",
doi = "10.1007/s13738-016-0895-x",
language = "English",
volume = "13",
pages = "1777--1783",
journal = "Journal of the Iranian Chemical Society",
issn = "1735-207X",
publisher = "Iranian Chemical Society",
number = "10",

}

TY - JOUR

T1 - Photoproducts of indomethacin

AU - Lin, Pen Yuan

AU - Chen, Fu An

AU - Wu, An Bang

AU - Chao, Su Hui

AU - Peng, Yu Tang

AU - Lee, Vickie M H

AU - Chen, Chau Yang

PY - 2016/10/1

Y1 - 2016/10/1

N2 - 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.

AB - 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.

KW - Indomethacin

KW - LC–ESI–MS

KW - Photoproduct

KW - β-Hydroxy-γ-lactone

UR - http://www.scopus.com/inward/record.url?scp=84982272592&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84982272592&partnerID=8YFLogxK

U2 - 10.1007/s13738-016-0895-x

DO - 10.1007/s13738-016-0895-x

M3 - Article

AN - SCOPUS:84982272592

VL - 13

SP - 1777

EP - 1783

JO - Journal of the Iranian Chemical Society

JF - Journal of the Iranian Chemical Society

SN - 1735-207X

IS - 10

ER -