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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/10 17:57:45」(JST)

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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

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

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 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.

References

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

This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.

UpToDate Contents

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English Journal

The Rebirth of Interest in Renal Tubular Function.

Lowenstein J1, Grantham JJ2.
American journal of physiology. Renal physiology.Am J Physiol Renal Physiol.2016 Mar 2:ajprenal.00055.2016. doi: 10.1152/ajprenal.00055.2016. [Epub ahead of print]
The measurement of glomerular filtration rate by the clearance of inulin or creatinine has evolved over the past fifty years into an estimated value (eGFR) based solely on plasma creatinine concentration. We have examined some of the misconceptions and misunderstanding of the classification of renal
PMID 26936872

Untargeted plasma and tissue metabolomics in rats with chronic kidney disease given AST-120.

Velenosi TJ1, Hennop A1, Feere DA1, Tieu A1, Kucey AS1, Kyriacou P2, McCuaig LE1, Nevison SE1, Kerr MA2, Urquhart BL1,3,4.
Scientific reports.Sci Rep.2016 Mar 2;6:22526. doi: 10.1038/srep22526.
Chronic kidney disease (CKD) results in the accumulation of metabolic waste products that are normally cleared by the kidney, known as uremia. Many of these waste products are from bacteria metabolites in the gut. Accumulation of uremic toxins in plasma and tissue, as well as the gut-plasma-tissue m
PMID 26932318

A urinary metabonomics analysis of long-term effect of acetochlor exposure on rats by ultra-performance liquid chromatography/mass spectrometry.

Li L1, Wang M2, Chen S3, Zhao W1, Zhao Y1, Wang X1, Zhang Y4.
Pesticide biochemistry and physiology.Pestic Biochem Physiol.2016 Mar;128:82-8. doi: 10.1016/j.pestbp.2015.09.013. Epub 2015 Sep 28.
The study was to assess the long-term toxic effects of acetochlor on rats. Two different doses (42.96 and 107.4mg/kgbodyweight/day) of acetochlor were administered to Wistar rats through their food for over 24weeks. Rat urine samples were collected at two time-points for the measurements of the meta
PMID 26969444

Japanese Journal

Discrimination between Campylobacter jejuni and C. coli Using a Macrolide and Quinolone Line Probe Assay (MQ-LiPA)

NIWA Hidekazu,ASAI Yoshio,YAMAI Shiro,ITOH Kikuji
Bioscience and microflora 26(3), 71-74, 2007-07-01
… coli by the hippurate hydrolysis test, three PCR methods using C. … coli by the hippurate hydrolysis test but as C. … These results suggest that MQ-LiPA is an effective method and can replace the hippurate hydrolysis test as other PCR methods. …
NAID 10019729593

血清蛋白結合に関連した臨床検査値の解釈(誌上シンポジウム)

高村徳人,徳永仁,有森和彦
藥學雜誌 127(2), 231-236, 2007-02-01
… BUN data are associated with the amounts of several uremic toxins, 3-carboxy-4-methyl-5-propyl-2-furanpropanate (CMPF), indole-3-acetate (IA), indoxyl sulfate (IS) and hippurate (HA). …
NAID 110006163774

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★リンクテーブル★

リンク元	「馬尿酸」「馬尿酸塩」
拡張検索	「p-aminohippurate sodium」「methenamine hippurate」「aminohippurate」「sodium paraaminohippurate clearance」

「馬尿酸」

Hippuric acid
Names
	IUPAC name Benzoylaminoethanoic acid
	Other names Hippuric acid, N-benzoylglycine, benzoyl glycocoll, benzoyl amidoacetic acid
Identifiers
CAS Registry Number	495-69-2
ChEBI	CHEBI:18089
ChEMBL	ChEMBL461
ChemSpider	451
	InChI InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12) ; Key: QIAFMBKCNZACKA-UHFFFAOYSA-N ; InChI=1/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12); Key: QIAFMBKCNZACKA-UHFFFAOYAD ;
Jmol-3D images	Image
KEGG	C01586
PubChem	464
	SMILES c1ccc(cc1)C(=O)NCC(=O)O ;
UNII	TE0865N2ET
Properties
Chemical 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)
Hazards
Safety data sheet	Material Safety Data Sheet
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references