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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/28 14:46:01」(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 hydrazoic acid.

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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1. ポルフィリン症：概要 porphyrias an overview
2. 先天性代謝異常：代謝性救急疾患 inborn errors of metabolism metabolic emergencies
3. 単純性および混合性酸塩基障害 simple and mixed acid base disorders
4. 嚢胞性線維症：肝胆道系疾患 cystic fibrosis hepatobiliary disease
5. 酸塩基障害におけるカリウムバランス potassium balance in acid base disorders

English Journal

Consumption of Hibiscus sabdariffa L. aqueous extract and its impact on systemic antioxidant potential in healthy subjects.

Frank T, Netzel G, Kammerer DR, Carle R, Kler A, Kriesl E, Bitsch I, Bitsch R, Netzel M.SourcePrivate Consultant, 65812 Bad Soden, Germany.
Journal of the science of food and agriculture.J Sci Food Agric.2012 Aug 15;92(10):2207-18. doi: 10.1002/jsfa.5615. Epub 2012 Feb 13.
BACKGROUND: To evaluate health benefits attributed to Hibiscus sabdariffa L. a randomized, open-label, two-way crossover study was undertaken to compare the impact of an aqueous H. sabdariffa L. extract (HSE) on the systemic antioxidant potential (AOP; assayed by ferric reducing antioxidant power (F
PMID 22331521

The glycine deportation system and its pharmacological consequences.

Beyoğlu D, Idle JR.AbstractThe glycine deportation system is an essential component of glycine catabolism in man whereby 400 to 800mg glycine per day are deported into urine as hippuric acid. The molecular escort for this deportation is benzoic acid, which derives from the diet and from gut microbiota metabolism of dietary precursors. Three components of this system, involving hepatic and renal metabolism, and renal active tubular secretion help regulate systemic and central nervous system levels of glycine. When glycine levels are pathologically high, as in congenital nonketotic hyperglycinemia, the glycine deportation system can be upregulated with pharmacological doses of benzoic acid to assist in normalization of glycine homeostasis. In congenital urea cycle enzymopathies, similar activation of the glycine deportation system with benzoic acid is useful for the excretion of excess nitrogen in the form of glycine. Drugs which can substitute for benzoic acid as substrates for the glycine deportation system have adverse reactions that may involve perturbations of glycine homeostasis. The cancer chemotherapeutic agent ifosfamide has an unacceptably high incidence of encephalopathy. This would appear to arise as a result of the production of toxic aldehyde metabolites which deplete ATP production and sequester NADH in the mitochondrial matrix, thereby inhibiting the glycine deportation system and causing de novo glycine synthesis by the glycine cleavage system. We hypothesize that this would result in hyperglycinemia and encephalopathy. This understanding may lead to novel prophylactic strategies for ifosfamide encephalopathy. Thus, the glycine deportation system plays multiple key roles in physiological and neurotoxicological processes involving glycine.
Pharmacology & therapeutics.Pharmacol Ther.2012 Aug;135(2):151-67. Epub 2012 May 11.
The glycine deportation system is an essential component of glycine catabolism in man whereby 400 to 800mg glycine per day are deported into urine as hippuric acid. The molecular escort for this deportation is benzoic acid, which derives from the diet and from gut microbiota metabolism of dietary pr
PMID 22584143

Japanese Journal

Direct inhibition and down-regulation by uremic plasma components of hepatic uptake transporter for sn-38, an active metabolite of irinotecan, in humans

Fujita Ken-ichi,Sugiura Tomoko,Okumura Hidenori,Umeda Saki,Nakamichi Noritaka,Watanabe Yusuke,Suzuki Hiromichi,Sunakawa Yu,Shimada Ken,Kawara Kaori,Sasaki Yasutsuna,Kato Yukio
Pharmaceutical Research 31(1), 204-215, 2014-01
… Methods: We evaluated SN-38 uptake and its inhibition by uremic toxins, 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF), indoxyl sulfate (Indox), hippuric acid (HA) and indole acetate (IA), with cryopreserved human hepatocytes and HEK293 cells stably expressing hepatic uptake transporters, organic anion transporting polypeptides (OATPs). …
NAID 120005385991

Correlation between Serum Levels of Protein-Bound Uremic Toxins in Hemodialysis Patients Measured by LC/MS/MS

Itoh Yoshiharu,Ezawa Atsuko,Kikuchi Kaori,Tsuruta Yoshinari,Niwa Toshimitsu
Mass Spectrometry 2(Special_Issue), S0017-S0017, 2013
… Serum concentration of protein-bound uremic toxins such as indoxyl sulfate, indoxyl glucuronide, indoleacetic acid, p-cresyl sulfate, p-cresyl glucuronide, phenyl sulfate, phenyl glucuronide, phenylacetic acid, phenylacetylglutamine, hippuric acid, 4-ethylphenyl sulfate, and 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid (CMPF) in hemodialysis patients were simultaneously measured by liquid chromatography/tandem mass spectrometry. …
NAID 130003380185

有機溶剤中毒予防のための尿中馬尿酸の光学的検知の研究 : 馬尿酸溶液の近赤外吸光スペクトルの検討

西田亘児,小川充洋,斎藤淳夫 [他],范宇亭,本井幸介,山越健弘,山越憲一
電子情報通信学会技術研究報告. MBE, MEとバイオサイバネティックス 111(57), 9-13, 2011-05-13
有機溶剤として広く用いられるトルエンの最終代謝物は馬尿酸であり,トルエン作業者の尿中には馬尿酸が含まれる.この尿中馬尿酸はトルエン暴露の指標となるため,トルエン作業者には尿検査が義務づけられている.現在,こうした計測のためにはHPLCなどが用いられているが,本研究では,簡便で即時にできる検査の開発を目指し,近赤外吸光スペクトラム計測に着目した.今回,馬尿酸水溶液の近赤外吸光スペクトルを計測し,純水 …
NAID 110008726107

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★リンクテーブル★

リンク元	「馬尿酸」「hippurate」
拡張検索	「aminohippuric acid」

「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) (decomposes)
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