Document Detail


The aromatization of cyclohexanecarboxylic acid to hippuric acid: substrate specificity and species differences.
MedLine Citation:
PMID:  4047028     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The ability to convert cyclohexanecarboxylic acid to hippuric acid has been studied in liver from guinea pigs, rabbits, rats and mice using a gas chromatographic - mass spectrometric method employing selected ion monitoring. Guinea pig liver showed the highest activity, giving values double of those found in rabbit liver and five times those in rat liver. Only very weak activity was found in mouse liver. (Hydroxymethyl)cyclohexane, cyclohexanealdehyde and alpha-hydroxyethylcyclohexane, which are structurally related to cyclohexanecarboxylic acid but lack the carboxyl group, were not aromatized by guinea pig liver mitochondria. This finding indicates that the carboxyl group is essential for aromatization. Absence of aromatization was also found with the homologs cyclohexaneacetic acid and cyclohexanepropionic acid and with the di-acids trans-1,2- and trans-1,4-cyclohexanedicarboxylic acid. The effect of a methyl group in cyclohexanecarboxylic acid depended on its position. 2-Methyl-1-cyclohexanecarboxylic acid was not aromatized, however the 3- and 4-methyl derivatives underwent aromatization and subsequent conjugation with glycine. The rates of formation of m-methyl- and p-methylhippuric acid were 16% and 9%, respectively, of that found for hippuric acid from cyclohexanecarboxylic acid (8.0 nmol/min/mg protein).
Authors:
A M Svardal; R R Scheline
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Publication Detail:
Type:  Comparative Study; In Vitro; Journal Article    
Journal Detail:
Title:  Molecular and cellular biochemistry     Volume:  67     ISSN:  0300-8177     ISO Abbreviation:  Mol. Cell. Biochem.     Publication Date:  1985 Jul 
Date Detail:
Created Date:  1985-11-13     Completed Date:  1985-11-13     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0364456     Medline TA:  Mol Cell Biochem     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  171-9     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Animals
Benzoates / metabolism,  pharmacology
Benzoic Acid
Biotransformation
Chemical Phenomena
Chemistry
Cyclohexanecarboxylic Acids / metabolism*
Enzymes / metabolism
Guinea Pigs
Hippurates / metabolism*
Liver / drug effects,  metabolism*
Male
Mice
Rabbits
Rats
Species Specificity
Substrate Specificity
Chemical
Reg. No./Substance:
0/Benzoates; 0/Cyclohexanecarboxylic Acids; 0/Enzymes; 0/Hippurates; 495-69-2/hippuric acid; 65-85-0/Benzoic Acid; 98-89-5/cyclohexanecarboxylic acid

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


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