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Hippuric acid

 
Sci-Tech Dictionary: hippuric acid
 
(hi′pyu̇r·ik ′as·əd)

(organic chemistry) C6H5CONHCH2·COOH Colorless crystals melting at 188°C; soluble in hot water, alcohol, and ether; used in medicine and as a chemical intermediate.


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Veterinary Dictionary: hippuric acid
 

A compound formed by conjugation of benzoic acid and glycine; it occurs in the urine of herbivorous animals, rarely in human urine.

  • h. acid test — has been tested as a means of assessing hepatic efficiency but is not favored.
 
Wikipedia: Hippuric acid
Top
Hippuric acid
IUPAC name
Other names Hippuric acid, N-benzoylglycine, benzoyl glycocoll, benzoyl amidoacetic acid
Identifiers
CAS number [495-69-2]
PubChem 464
SMILES
Properties
Molecular formula C9H9NO3
Molar mass 179.17 g/mol
Melting point

187 - 188 °C

Boiling point

240 °C (dec.)

Hazards
MSDS MSDS from Oxford University
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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 can also indicate a toluene intoxication. 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.

Contents

Synthesis

A modern synthesis of hippuric acid involves the acylation of glycine with benzoyl chloride:[1]

Reactions

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

Justus von Liebig showed in 1829 that hippuric acid differed from benzoic acid, and in 1839 determined its constitution, while in 1873 Victor Dessaignes synthesized it by the action of benzoyl chloride on the zinc salt of glycine.[2] It was also formed by heating benzoic anhydride with glycine, [3] and by heating benzamide with monochloroacetic acid.

See also

References

  1. ^ A. W. Ingersoll and S. H. Babcock. "Hippuric acid". Org. Synth.; Coll. Vol. 2: 0328. 
  2. ^ Dessaignes V. (1853). "Ueber die Regeneration der Hippursäure". Annalen der Chemie und Pharmacie 87 (3): 325–327. doi:10.1002/jlac.18530870311. 
  3. ^ Curtius T. (1884). "Synthese von Hippursäure und Hippursäureäthern". Berichte der deutschen chemischen Gesellschaft 17 (2): 1662–1663. doi:10.1002/cber.18840170225. 

 
 

 

Copyrights:

Sci-Tech Dictionary. McGraw-Hill Dictionary of Scientific and Technical Terms. Copyright © 2003, 1994, 1989, 1984, 1978, 1976, 1974 by McGraw-Hill Companies, Inc. All rights reserved.  Read more
Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.  Read more
Wikipedia. This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Hippuric acid" Read more