Document Detail


Isolation and structure elucidation of the major photodegradation products of seratrodast.
MedLine Citation:
PMID:  18562149     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Photodegradation of seratrodast ([+/-]-7-(3,5,6-trimethyl-1,4-benzoquinone-2-yl)-7-phenyl-heptanoic acid, SD), a p-benzoquinone anti-asthmatic drug, has been investigated in different solutions. HPLC analysis showed that SD was degradated under UV irradiation at 254 nm to afford three major products (SD1, SD2 and SD3) in methanol and in acetonitrile/H2O solutions, while only two of them (SD2 and SD3) could be detected in acetonitrile solution. Furthermore, SD1 was unstable even when the samples were protected from light, so the acetylated SD1 (Ace-SD1) together with SD2 and SD3 were isolated by semi-preparative reversed-phase HPLC. The structures were elucidated as 6-(2,5-diacetoxy-3,4,6-trimethyl-phenyl)-7-phenyl-hept-6-enoic acid (Ace-SD1), 7-phenyl-6-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-hept-6-enoic acid (SD2) and 5-(5-hydroxy-4,6,7-trimethyl-2-phenyl-benzofuran-3-yl)-pentanoic acid (SD3) based on the spectral data of MS, UV spectrum, IR spectrum and NMR spectrum. Meanwhile, a possible route for the formation of these photoproducts was proposed, which might explain the generation procedure of SD1, SD2 and SD3 during UV irradiation.
Authors:
Jufang Xu; Yihua Zhang; Yuzhu Hu
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Publication Detail:
Type:  Journal Article     Date:  2008-05-13
Journal Detail:
Title:  Journal of pharmaceutical and biomedical analysis     Volume:  48     ISSN:  0731-7085     ISO Abbreviation:  J Pharm Biomed Anal     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-08-26     Completed Date:  2008-11-26     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8309336     Medline TA:  J Pharm Biomed Anal     Country:  England    
Other Details:
Languages:  eng     Pagination:  78-84     Citation Subset:  IM    
Affiliation:
Key Laboratory of Drug Quality Control and Pharmacovigilance, Ministry of Education, Nanjing 210009, China.
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MeSH Terms
Descriptor/Qualifier:
Acetonitriles / chemistry
Anti-Asthmatic Agents / chemistry*,  radiation effects*
Benzoquinones / chemistry*,  radiation effects*
Chromatography, High Pressure Liquid
Heptanoic Acids / chemistry*,  radiation effects*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Methanol / chemistry
Molecular Structure
Photolysis*
Solutions / chemistry
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Ultraviolet Rays
Water / chemistry
Chemical
Reg. No./Substance:
0/Acetonitriles; 0/Anti-Asthmatic Agents; 0/Benzoquinones; 0/Heptanoic Acids; 0/Solutions; 112665-43-7/seratrodast; 67-56-1/Methanol; 75-05-8/acetonitrile; 7732-18-5/Water

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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