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

doi:10.1007/s13738-016-0895-x

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 journal › Article › peer-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 language	English
Pages (from-to)	1777-1783
Number of pages	7
Journal	Journal of the Iranian Chemical Society
Volume	13
Issue number	10
DOIs	https://doi.org/10.1007/s13738-016-0895-x
Publication status	Published - Oct 1 2016
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Chemistry(all)

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10.1007/s13738-016-0895-x

Cite this

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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 An-Bang Wu and Chao, {Su Hui} and Peng, {Yu Tang} and Lee, {Vickie M.H.} and Chen, {Chau Yang}",

note = "Funding Information: The authors thank Cheng{\textquoteright}s Foundation for Pharmaceutical Sciences for financial support. Appreciation is also due to Professor Tsuoh-Min Juang at National Chiao Tung University for carrying out the single-crystal X-ray analysis and Dr. David Hsiao at Institute of Molecular Biology, Academia Sinica for the helpful discussion. Publisher Copyright: {\textcopyright} 2016, Iranian Chemical Society.",

year = "2016",

month = oct,

day = "1",

doi = "10.1007/s13738-016-0895-x",

language = "English",

volume = "13",

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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

N1 - Funding Information: The authors thank Cheng’s Foundation for Pharmaceutical Sciences for financial support. Appreciation is also due to Professor Tsuoh-Min Juang at National Chiao Tung University for carrying out the single-crystal X-ray analysis and Dr. David Hsiao at Institute of Molecular Biology, Academia Sinica for the helpful discussion. Publisher Copyright: © 2016, Iranian Chemical Society.

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

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EP - 1783

JO - Journal of the Iranian Chemical Society

JF - Journal of the Iranian Chemical Society

IS - 10

ER -

Photoproducts of indomethacin

Abstract

Keywords

ASJC Scopus subject areas

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