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Revision as of 11:51, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 02:18, 23 December 2024 edit undoThoughtWarden (talk | contribs)Extended confirmed users950 edits Open access status updates in citations with OAbot #oabotTag: OAbot [2.1]
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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 415528640		| verifiedrevid = 443857913
	| ImageFile = Hippuric acid.png		| ImageFile = Hippuric acid.svg
	| ImageSize =
			| ImageAlt = Structural formula of hippuric acid
	| IUPACName = Benzoylaminoacetic acid
			| ImageFile1 = Hippuric acid.jpg
⚫	| OtherNames = Hippuric acid, N-benzoylglycine, benzoyl glycocoll, benzoyl amidoacetic acid
			| ImageAlt1 = Recrystallised hippuric acid
⚫	| Section1 = {{Chembox Identifiers
			| IUPACName = ''N''-Benzoylglycine
⚫	| UNII_Ref = {{fdacite|correct|FDA}}
			| PIN = Benzamidoacetic acid
		⚫	| OtherNames = {{ubl|Hippuric acid|Benzoyl glycocoll|Benzoyl amidoacetic acid}}
		⚫	| Section1 = {{Chembox Identifiers
		⚫	| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = TE0865N2ET		| UNII = TE0865N2ET
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 495-69-2		| CASNo = 495-69-2
	| PubChem = 464		| PubChem = 464
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID=451		| ChemSpiderID =451
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 18089		| ChEBI = 18089
	| SMILES = c1ccc(cc1)C(=O)NCC(=O)O		| SMILES = OC(=O)CNC(=O)c1ccccc1
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
			| C=9 | H=9 | N=1 | O=3
	| Formula = C<sub>9</sub>H<sub>9</sub>NO<sub>3</sub>
		⚫	| Appearance =
	| MolarMass = 179.17 g/mol
			| Density = 1.371 g/cm<sup>3</sup>
⚫	| Appearance =
	| Density =		| MeltingPtC = 187 to 188
			| MeltingPt_notes =
	| MeltingPt = 187 - 188 °C
	| BoilingPt = 240 °C (dec.)		| BoilingPtC = 240
			| BoilingPt_notes = (decomposes)
	| Solubility =		| Solubility =
⚫	}}
⚫	| Section3 = {{Chembox Hazards
	| ExternalMSDS =
⚫	| MainHazards =
⚫	| FlashPt =
	| Autoignition =
	}}		}}
		⚫	| Section3 = {{Chembox Hazards
			| ExternalSDS =
		⚫	| MainHazards =
		⚫	| FlashPt =
			| AutoignitionPt =
		⚫	}}
	}}		}}
⚫	'''Hippuric acid''' (] ''hippos'', horse, ''ouron'', urine) is a ] found in the ] of ]s and other herbivores. Hippuric acid crystallizes in ] 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 ], however, scientists have called this correlation into question because there are other variables that influence levels of hippuric acid.<ref>http://www.ncbi.nlm.nih.gov/pubmed/19891605</ref><ref>http://en.wikipedia.org/wiki/Toluene_%28toxicology%29#Measure_of_exposure</ref> When many aromatic compounds such as ] and ] are taken internally, they are converted to hippuric acid by reaction with the ], ].
			'''Hippuric acid''' (] ''hippos'', horse, ''ouron'', urine) is a ] and organic compound. It is found in ] and is formed from the combination of ] and ]. Levels of hippuric acid rise with the consumption of ] (such as in ], ] and ]). The ] are first converted to ], and then to hippuric acid and excreted in ].<ref>{{cite HMDB|author1-link=David S. Wishart|url=http://www.hmdb.ca/metabolites/HMDB0000714|title=Showing metabocard for Hippuric acid (HMDB0000714)}}</ref>
		⚫	Hippuric acid crystallizes in ] prisms which are readily soluble in hot water, melt at 187&nbsp;°C, and decompose at about 240&nbsp;°C.<ref name="EB1911">{{EB1911|inline=y|wstitle=Hippuric Acid|volume=13|page=523}}</ref> High concentrations of hippuric acid may also indicate a ]; however, scientists have called this correlation into question because there are other variables that affect levels of hippuric acid.<ref>{{cite journal|pmid=19891605|year=2010|last1=Pero|first1=RW|title=Health consequences of catabolic synthesis of hippuric acid in humans|volume=5|issue=1|pages=67–73|journal=Current Clinical Pharmacology|doi=10.2174/157488410790410588}}</ref> When many aromatic compounds such as ] and ] are taken internally, they are converted to hippuric acid by reaction with the ], ].
	==Synthesis==		==Synthesis==
	A modern synthesis of hippuric acid involves the ] of ] with ]:<ref>{{OrgSynth | title = Hippuric acid | collvol = 2 | collvolpages = 0328 | prep = cv2p0328 | author = A. W. Ingersoll and S. H. Babcock}}</ref>		A modern synthesis of hippuric acid involves the ] of ] with ] ("]").<ref>{{OrgSynth | title = Hippuric acid | collvol = 2 | year = 1932 | volume = 12 | pages = 40 | collvolpages = 328 | prep = cv2p0328 | first1 = A. W. | last1 = Ingersoll | first2 = S. H. | last2 = Babcock | doi = 10.15227/orgsyn.012.0040}}</ref>
			:]
			== Physiology ==
	:]
			Biochemically, hippuric acid is produced from ] and glycine, which occurs in the liver, intestine, and kidneys.<ref>{{cite journal | vauthors = Wikoff WR, Anfora AT, Liu J, Schultz PG, Lesley SA, Peters EC, Siuzdak G|author-link7=Gary Siuzdak | title = Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites | journal = Proc. Natl. Acad. Sci. U.S.A. | volume = 106 | issue = 10 | pages = 3698–3703 | date = March 2009 | pmid = 19234110 | pmc = 2656143 | doi = 10.1073/pnas.0812874106|doi-access=free |bibcode=2009PNAS..106.3698W }}</ref> In terms of mechanism, benzoic acid is converted to ], an acylating agent.<ref>{{cite journal |pmid=8301581 |date=1994 |last1=Chiba |first1=M. |last2=Poon |first2=K. |last3=Hollands |first3=J. |last4=Pang |first4=K. S. |title=Glycine Conjugation Activity of Benzoic Acid and its Acinar Localization in the Perfused Rat Liver |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=268 |issue=1 |pages=409–416 }}</ref>
			Hippuric acid may be formed from the essential amino acid ] through at least two pathways. Phenylalanine undergoes ] to form an ], ], which can tautomerize to a reactive enol. The benzylic carbon is reactive which undergoes ] followed by the competing pathways to either react with the alpha carbon subsequently form an ] intermediate followed by formation of oxalic acid and benzaldehyde, or, peroxidation can react with the ] to form an alpha-keto-beta-peroxylactone intermediate followed by formation of ], ], and ]. Alternatively, under certain conditions, phenylpyruvic acid may undergo a redox mechanism, such as ] donating an electron, to directly release carbon dioxide, followed by carbon monoxide, for the formation of a stable toluene radical which is resolved by an antioxidant such as ascorbate. In all of the aforementioned cases, benzaldehyde undergoes biotransformation via ] to benzoic acid followed by conjugation to glycine for formation of hippurate which undergoes urinary excretion.<ref>{{Cite journal|last1=Hopper|first1=Christopher P.|last2=De La Cruz|first2=Ladie Kimberly|last3=Lyles|first3=Kristin V.|last4=Wareham|first4=Lauren K.|last5=Gilbert|first5=Jack A.|last6=Eichenbaum|first6=Zehava|last7=Magierowski|first7=Marcin|last8=Poole|first8=Robert K.|last9=Wollborn|first9=Jakob|last10=Wang|first10=Binghe|date=2020-12-23|title=Role of Carbon Monoxide in Host–Gut Microbiome Communication|journal=Chemical Reviews|language=en|volume=120|issue=24|pages=13273–13311|doi=10.1021/acs.chemrev.0c00586|pmid=33089988 |s2cid=224824871 |issn=0009-2665}}</ref> Similarly, toluene reacts with CYP450 to form benzaldehyde.<ref>{{Cite journal|last1=Hopper|first1=Christopher P.|last2=Zambrana|first2=Paige N.|last3=Goebel|first3=Ulrich|last4=Wollborn|first4=Jakob|date=2021|title=A brief history of carbon monoxide and its therapeutic origins|journal=Nitric Oxide|language=en|volume=111-112|pages=45–63|doi=10.1016/j.niox.2021.04.001 |pmid=33838343 |s2cid=233205099 |issn=1089-8603}}</ref>
			Hippuric acid has been reported to be a marker for ].<ref>{{cite news |title=Parkinson's smell test explained by science |url=https://www.bbc.com/news/uk-scotland-47627179 |access-date=11 March 2023 |work=BBC News |publisher=BBC |date=20 March 2019}}</ref>
	==Reactions==		==Reactions==
	Hippuric acid is readily ]d by hot caustic ]s to ] and glycine. ] converts it into ], C<sub>6</sub>H<sub>5</sub>C(=O)OCH<sub>2</sub>CO<sub>2</sub>H. Its ethyl ] reacts with ] to form hippuryl hydrazine, C<sub>6</sub>H<sub>5</sub>CONHCH<sub>2</sub>CONHNH<sub>2</sub>, which was used by ] for the preparation of ].		Hippuric acid is readily ]d by hot caustic ]s to ] and glycine. ] converts it into ], C<sub>6</sub>H<sub>5</sub>C(=O)OCH<sub>2</sub>CO<sub>2</sub>H.{{citation needed|date=October 2024}} Its ethyl ] reacts with ] to form hippuryl hydrazine, C<sub>6</sub>H<sub>5</sub>CONHCH<sub>2</sub>CONHNH<sub>2</sub>, which was used by ] for the preparation of ].<ref name="EB1911"/>
	==History==		==History==
			] showed in 1829 that hippuric acid differed from benzoic acid and he named it,<ref>{{cite journal |last1=Liebig |first1=Justus |title=Ueber die Säure, welche in dem Harn der grasfressenden vierfüssigen Thiere enthalten ist |journal=Annalen der Physik und Chemie |date=1829 |volume=17 |issue=11 |pages=389–399 |doi=10.1002/andp.18290931104 |bibcode=1829AnP....93..389L |url=https://zenodo.org/record/1883346 |trans-title=On the acid which is contained in the urine of grass-eating, four-footed animals |language=German}} Liebig named hippuric acid on p. 390: ''"Da ich die Säure aus dem Pferdeharn vorzugsweise untersucht habe, so werde ich sie, in Ermanglung eines passenderen Namens, mit Hippursäure bezeichnen."'' (Since I have especially investigated the acid from horse urine, then, for want of a more suitable name, I will designate it with "hippuric acid".)</ref> and in 1834 he determined its constitution,<ref>Liebig, Justus (1834) (On the composition of hippuric acid), ''Annalen der Physik und Chemie'', '''32''' : 573–574.</ref> while in 1853 French chemist ] (1800–1885) synthesized it by the action of ] on the zinc salt of glycine.<ref>{{cite journal
	] showed in 1829 that hippuric acid differed from benzoic acid, and in 1839 determined its constitution, while in 1873 ] synthesized it by the action of ] on the zinc salt of glycine.<ref>{{cite journal
	| title = Ueber die Regeneration der Hippursäure		| title = Ueber die Regeneration der Hippursäure
			|trans-title=On the regeneration of hippuric acid
	| author = Dessaignes V.		| author = Dessaignes V.
	| journal = Annalen der Chemie und Pharmacie		| journal = Annalen der Chemie und Pharmacie
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	| issue = 3		| issue = 3
	| pages = 325–327		| pages = 325–327
	| year = 1853		| year = 1853
			| url = https://zenodo.org/records/1427048/files/article.pdf
	| url =
	| doi = 10.1002/jlac.18530870311}}</ref> It was also formed by heating ] with glycine, <ref>{{cite journal		| doi = 10.1002/jlac.18530870311}} See also: Dessaignes (1853) ''Comptes rendus'', '''37''' : 251–252.</ref> It was also formed by heating ] with glycine,<ref>{{cite journal
	| title = Synthese von Hippursäure und Hippursäureäthern		| title = Synthese von Hippursäure und Hippursäureäthern
			|trans-title=Synthesis of hippuric acid and hippuric acid esters
	| author = ]		| author = Curtius T.
	| journal = Berichte der deutschen chemischen Gesellschaft		| journal = Berichte der Deutschen Chemischen Gesellschaft
	| volume = 17		| volume = 17
	| issue = 2		| issue = 2
	| pages = 1662–1663		| pages = 1662–1663
	| year = 1884		| year = 1884
	| url =		| url = https://zenodo.org/record/1425365
	| doi = 10.1002/cber.18840170225}}</ref> and by heating ] with ].		| doi = 10.1002/cber.18840170225|author-link=Theodor Curtius
			}}</ref> and by heating ] with ].<ref name="EB1911"/>
	==See also==		==See also==
	* ]		* ]
			* ]
			* ] (three different isomers)
	==References==		==References==
			{{reflist}}
	<references/>
	*{{1911}}
			{{Authority control}}
	]		]
	]		]
			]
			]
	]
	]
	]
	]
	]
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	]