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Ultraviolet-photoproduct of acetaminophen: Structure determination and evaluation of ecotoxicological effect

Paper ID Volume ID Publish Year Pages File Format Full-Text
26746 43974 2012 7 PDF Available
Title
Ultraviolet-photoproduct of acetaminophen: Structure determination and evaluation of ecotoxicological effect
Abstract

This study was focused on photodegradation of acetaminophen (AA) exposed to ultraviolet (UV) irradiation at 254 nm delivered by a system similar to that used for sterilization in sewage treatment plants. The degradation of AA during irradiation for up to 96 h was monitored by means of high-performance liquid chromatography (HPLC). Based on the mass/charge ratio (m/z) of the protonated ion and the mass fragmentation pattern in electrospray ionization time-of-flight mass spectrometry (ESI-TOF/MS/MS), the photoproduct was identified as 1-(2-amino-5-hydroxyphenyl)ethanone (1). Examination of toxicity by means of a luminescent bacteria test (ISO11348) indicated that AA solution was nontoxic, whereas photo-exposed AA solution was toxic (EC50: 29.46 mg/L). The toxicity of synthetic compound 1 was shown to account for a substantial part of the toxicity of photo-exposed AA. These results indicate the importance of investigating not only parent compounds, but also photoproducts the risk assessment of pharmaceuticals in aquatic environments.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Photodegradation of acetaminophen and the generation of its photoproduct by UV irradiation were examined. ► The photoproduct was 1-(2-amino-5-hydroxyphenyl)ethanone. ► Acetaminophen solution had no effect on aquatic organisms. ► Photo-exposed acetaminophen solution showed marked toxicity for aquatic organisms. ► Synthetic 1-(2-amino-5-hydroxyphenyl)ethanone showed toxicity stronger than acetaminophen solution.

Keywords
AA, acetaminophen; UV, ultraviolet; STP, sewage treatment plant; HPLC, high-performance liquid chromatography; ESI-TOF/MS/MS, electrospray ionization time-of-flight mass spectrometry; EC50, median effective concentration; S.D., standard deviation; PA, p-a
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Ultraviolet-photoproduct of acetaminophen: Structure determination and evaluation of ecotoxicological effect
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 249, 1 December 2012, Pages 29–35
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us