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

doi:10.1016/j.tetlet.2004.08.177

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 journal › Article › peer-review

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 language	English
Pages (from-to)	8107-8109
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2004.08.177
Publication status	Published - Oct 18 2004

Keywords

LC-ESI-MS
Photoproducts
Tolmetin

ASJC Scopus subject areas

Drug Discovery
Biochemistry
Organic Chemistry

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10.1016/j.tetlet.2004.08.177

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title = "Photolysis of NSAIDs. Part 3: Structural elucidation of photoproducts of tolmetin in methanol",

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.",

keywords = "LC-ESI-MS, Photoproducts, Tolmetin",

author = "Sheu, {Ming Thau} and Jender Wu and Chen, {Chih Jui} and Chao, {Su Hui} and An-Bang Wu",

year = "2004",

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TY - JOUR

T1 - Photolysis of NSAIDs. Part 3

T2 - Structural elucidation of photoproducts of tolmetin in methanol

AU - Sheu, Ming Thau

AU - Wu, Jender

AU - Chen, Chih Jui

AU - Chao, Su Hui

AU - Wu, An-Bang

PY - 2004/10/18

Y1 - 2004/10/18

N2 - 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.

AB - 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.

KW - LC-ESI-MS

KW - Photoproducts

KW - Tolmetin

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

Abstract

Keywords

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