Hippuric acid

Hippuric acid
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
Melting point

187 - 188 °C

Boiling point

240 °C (dec.)

Hazards
MSDS MSDS from Oxford University
 YesY acid (verify) (what is: YesY/N?)
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 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][2] 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:[3]

Preparation of hippuric acid.png

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.[4] It was also formed by heating benzoic anhydride with glycine,[5] and by heating benzamide with monochloroacetic acid.

See also

References

  1. ^ Pero, RW (2010). "Health consequences of catabolic synthesis of hippuric acid in humans". Current clinical pharmacology 5 (1): 67–73. PMID 19891605. 
  2. ^ http://en.wikipedia.org/wiki/Toluene_%28toxicology%29#Measure_of_exposure
  3. ^ A. W. Ingersoll and S. H. Babcock, "Hippuric acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0328 ; Coll. Vol. 2: 0328 
  4. ^ Dessaignes V. (1853). "Ueber die Regeneration der Hippursäure". Annalen der Chemie und Pharmacie 87 (3): 325–327. doi:10.1002/jlac.18530870311. 
  5. ^ Curtius T. (1884). "Synthese von Hippursäure und Hippursäureäthern". Berichte der deutschen chemischen Gesellschaft 17 (2): 1662–1663. doi:10.1002/cber.18840170225. 

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Look at other dictionaries:

  • Hippuric acid — Hippuric Hip*pu ric, a. [Gr. i ppos horse + o y ron urine: cf. F. hippurique.] (Physiol. Chem.) Obtained from the urine of horses; as, hippuric acid. [1913 Webster] {Hippuric acid}, a white crystalline substance, containing nitrogen, present in… …   The Collaborative International Dictionary of English

  • hippuric acid — hippuric acid. См. бензоилглицин. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • hippuric acid — hipuro rūgštis statusas T sritis chemija formulė C₆H₅CONHCH₂COOH atitikmenys: angl. hippuric acid rus. гиппуровая кислота ryšiai: sinonimas – benzenkarbonilaminoetano rūgštis …   Chemijos terminų aiškinamasis žodynas

  • hippuric acid — A detoxification and excretory product of benzoate found in the urine of humans and many herbivorous animals; used therapeutically in the form of its salts (hippurates of calcium and ammonium). [G. hippos, horse, + ouron, urine] * * * hip·pu·ric… …   Medical dictionary

  • hippuric acid — (ˈ)hi|pyu̇rik noun Etymology: hipp + uric : a white crystalline nitrogenous acid C6H5CONHCH2COOH formed in the liver as a detoxication product of benzoic acid and present in the urine of herbivorous animals and in small quantity in human urine… …   Useful english dictionary

  • hippuric acid — [hɪ pjʊərɪk] noun Biochemistry an organic acid present in the urine of herbivores and other mammals. Origin C19: from Gk hippos horse + ouron urine + ic …   English new terms dictionary

  • hippuric acid — noun A benzoyl derivative of glycine; it occurs in the urine of herbivores …   Wiktionary

  • Hippuric — Hip*pu ric, a. [Gr. i ppos horse + o y ron urine: cf. F. hippurique.] (Physiol. Chem.) Obtained from the urine of horses; as, hippuric acid. [1913 Webster] {Hippuric acid}, a white crystalline substance, containing nitrogen, present in the urine… …   The Collaborative International Dictionary of English

  • hippuric — adjective Of or pertaining to hippuric acid or its derivatives …   Wiktionary

  • hippuric — /hip ūˈrik/ adjective Denoting an acid, first obtained from the urine of horses, occurring in the urine of many animals, particularly in that of herbivores and rarely in that of human beings ORIGIN: ↑hipp and Gr ouron urine …   Useful english dictionary

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