| Advanced oxidation chemistry of paracetamol. UV/H(2)O(2)-induced hydroxylation/degradation pathways and (15)N-aided inventory of nitrogenous breakdown products. | |
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MedLine Citation:
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PMID: 12182655 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The advanced oxidation chemistry of the antipyretic drug paracetamol (1) with the UV/H(2)O(2) system was investigated by an integrated methodology based on (15)N-labeling and GC-MS, HPLC, and 2D (1)H, (13)C, and (15)N NMR analysis. Main degradation pathways derived from three hydroxylation steps, leading to 1,4-hydroquinone/1,4-benzoquinone, 4-acetylaminocatechol and, to a much lesser extent, 4-acetylaminoresorcine. Oxidation of the primary aromatic intermediates, viz. 4-acetylaminocatechol, 1,4-hydroquinone, 1,4-benzoquinone, and 1,2,4-benzenetriol, resulted in a series of nitrogenous and non-nitrogenous degradation products. The former included N-acetylglyoxylamide, acetylaminomalonic acid, acetylaminohydroxymalonic acid, acetylaminomaleic acid, diastereoisomeric 2-acetylamino-3-hydroxybutanedioic acids, 2-acetylaminobutenedioic acid, 3-acetylamino-4-hydroxy-2-pentenedioic acid, and 2,4-dihydroxy-3-acetylamino-2-pentenedioic acid, as well as two muconic and hydroxymuconic acid derivatives. (15)N NMR spectra revealed the accumulation since the early stages of substantial amounts of acetamide and oxalic acid monoamide. These results provide the first insight into the advanced oxidation chemistry of a 4-aminophenol derivative by the UV/H(2)O(2) system, and highlight the investigative potential of integrated GC-MS/NMR methodologies based on (15)N-labeling to track degradation pathways of nitrogenous species. |
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Authors:
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Davide Vogna; Raffaele Marotta; Alessandra Napolitano; Marco D'Ischia |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 67 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2002 Aug |
Date Detail:
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Created Date: 2002-08-16 Completed Date: 2003-03-13 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 6143-51 Citation Subset: IM |
Affiliation:
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Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Via Cinthia 4, I-80126 Naples, Italy. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acetaminophen
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chemistry*,
radiation effects Analgesics, Non-Narcotic / chemistry*, radiation effects Benzoquinones / chemistry Chemistry, Organic / methods Chromatography, High Pressure Liquid Gas Chromatography-Mass Spectrometry Hydrogen Peroxide / diagnostic use Hydroxylation Magnetic Resonance Spectroscopy Molecular Structure Nitrogen / chemistry* Nitrogen Isotopes / chemistry, diagnostic use Oxidation-Reduction Stereoisomerism Ultraviolet Rays / diagnostic use |
| Chemical | |
Reg. No./Substance:
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0/Analgesics, Non-Narcotic; 0/Benzoquinones; 0/Nitrogen Isotopes; 103-90-2/Acetaminophen; 106-51-4/benzoquinone; 7722-84-1/Hydrogen Peroxide; 7727-37-9/Nitrogen |
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