Document Detail


The enantioselective metabolism of 4-isopropenyltoluene in rabbits.
MedLine Citation:
PMID:  7703959     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
4-Isopropenyltoluene (8) was administered orally to rabbits and the following four optically active metabolites, 2-(p-tolyl)propanoic acid (10), p-(1-carboxyethyl)benzoic acid (11), 2-hydroxy-2-(p-tolyl)propanoic acid (12), and 2-(p-tolyl)-1,2-propanediol (13) were isolated from urine in addition to an optically inactive metabolite, 4-isopropenylbenzoic acid (9). The enantiomeric ratios of the metabolites 10 and 11 were respectively R/S = 33:67 and 39:61 (S predominance), whereas those of the metabolites 12 and 13 possessing a tertiary hydroxyl group were R/S = 77:23 and 84:16 respectively (R predominance). The presumed metabolic pathways of 8 in rabbits leading to these metabolites are discussed.
Authors:
T Matsumoto; T Ishida; Y Takeda; J Yagi
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Biological & pharmaceutical bulletin     Volume:  17     ISSN:  0918-6158     ISO Abbreviation:  Biol. Pharm. Bull.     Publication Date:  1994 Nov 
Date Detail:
Created Date:  1995-05-08     Completed Date:  1995-05-08     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9311984     Medline TA:  Biol Pharm Bull     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  1441-5     Citation Subset:  IM    
Affiliation:
Faculty of Integrated Arts and Sciences, University of Tokushima, Japan.
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MeSH Terms
Descriptor/Qualifier:
Animals
Benzoates / urine
Benzoic Acids*
Female
Magnetic Resonance Spectroscopy
Male
Mass Spectrometry
Phenylacetates / urine
Propionates / urine
Propylene Glycols / urine
Rabbits
Spectrophotometry, Infrared
Stereoisomerism
Structure-Activity Relationship
Styrenes / administration & dosage,  metabolism*
Toluene / analogs & derivatives,  urine
Chemical
Reg. No./Substance:
0/Benzoates; 0/Benzoic Acids; 0/Phenylacetates; 0/Propionates; 0/Propylene Glycols; 0/Styrenes; 108-88-3/Toluene; 145679-19-2/4-(1-carboxyethyl)benozic acid; 3333-13-9/4-isopropenyltoluene; 536-66-3/cumic acid; 56031-84-6/2-hydroxy-2-(4-tolyl)propanoic acid; 88416-64-2/2-(4-tolyl)-1,2-propanediol; 938-94-3/2-(4-tolyl)propanoic acid

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


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