Hippuric acid

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Hippuric acid
Hippuric acid.png
Identifiers
CAS number 495-69-2 YesY
PubChem 464
ChemSpider 451 YesY
UNII TE0865N2ET YesY
KEGG C01586 YesY
ChEBI CHEBI:18089 YesY
ChEMBL CHEMBL461 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H9NO3
Molar mass 179.17 g/mol
Density 1,371 g/cm3
Melting point 187 to 188 °C (369 to 370 °F; 460 to 461 K)
Boiling point 240 °C (464 °F; 513 K) (decomposes)
Hazards
MSDS Material Safety Data Sheet
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Hippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C and decompose at about 240 °C. High concentrations of hippuric acid may also indicate a toluene intoxication; however, scientists have called this correlation into question because there are other variables that influence levels of hippuric acid.[1] When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.

Synthesis[edit]

A modern synthesis of hippuric acid involves the acylation of glycine with benzoyl chloride:[2]

Preparation of hippuric acid.png

Reactions[edit]

Hippuric acid is readily hydrolysed by hot caustic alkalis to benzoic acid and glycine. Nitrous acid converts it into benzoyl glycolic acid, C6H5C(=O)OCH2CO2H. Its ethyl ester reacts with hydrazine to form hippuryl hydrazine, C6H5CONHCH2CONHNH2, which was used by Theodor Curtius for the preparation of azoimide.

History[edit]

Justus von Liebig showed in 1829 that hippuric acid differed from benzoic acid, and in 1839 determined its constitution, while in 1853 Victor Dessaignes synthesized it by the action of benzoyl chloride on the zinc salt of glycine.[3] It was also formed by heating benzoic anhydride with glycine,[4] and by heating benzamide with monochloroacetic acid.

See also[edit]

References[edit]

  1. ^ Pero, RW (2010). "Health consequences of catabolic synthesis of hippuric acid in humans". Current clinical pharmacology 5 (1): 67–73. doi:10.2174/157488410790410588. PMID 19891605. 
  2. ^ A. W. Ingersoll and S. H. Babcock, "Hippuric acid", Org. Synth. ; Coll. Vol. 2: 0328 
  3. ^ Dessaignes V. (1853). "Ueber die Regeneration der Hippursäure". Annalen der Chemie und Pharmacie 87 (3): 325–327. doi:10.1002/jlac.18530870311. 
  4. ^ Curtius T. (1884). "Synthese von Hippursäure und Hippursäureäthern". Berichte der deutschen chemischen Gesellschaft 17 (2): 1662–1663. doi:10.1002/cber.18840170225.