| The aromatization of cyclohexanecarboxylic acid to hippuric acid: substrate specificity and species differences. | |
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MedLine Citation:
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PMID: 4047028 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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). |
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Authors:
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A M Svardal; R R Scheline |
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Publication Detail:
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Type: Comparative Study; In Vitro; Journal Article |
Journal Detail:
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Title: Molecular and cellular biochemistry Volume: 67 ISSN: 0300-8177 ISO Abbreviation: Mol. Cell. Biochem. Publication Date: 1985 Jul |
Date Detail:
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Created Date: 1985-11-13 Completed Date: 1985-11-13 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 0364456 Medline TA: Mol Cell Biochem Country: NETHERLANDS |
Other Details:
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Languages: eng Pagination: 171-9 Citation Subset: IM |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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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:
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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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