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Revision as of 06:18, 29 June 2011 editZéroBot (talk | contribs)704,777 editsm r2.7.1) (robot Adding: fr:Acide urocanique← Previous edit		Latest revision as of 14:22, 25 October 2024 edit undoMonkbot (talk | contribs)Bots3,695,952 editsm Task 20: replace {lang-??} templates with {langx|??} ‹See Tfd› (Replaced 1);Tag: AWB
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	{{chembox		{{chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 397901863		| verifiedrevid = 436802684
	|ImageFile=Urocanic acid.svg		| ImageFile =Urocanic acid.svg
	|ImageSize=		| ImageSize =
	|IUPACName=(''E'')-3-(1''H''-imidazol-4-yl)prop-2-enoic acid		| PIN = (2''E'')-3-(1''H''-imidazol-4-yl)prop-2-enoic acid
	|OtherNames=		| OtherNames = (''E'')-3-(1''H''-imidazol-4-yl)acrylic acid
	|Section1= {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=104-98-3		| CASNo =104-98-3
	| PubChem=1178
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| SMILES=C1=C(NC=N1)C=CC(=O)O
			| UNII = G8D26XJJ3B
⚫	| MeSHName=Urocanic+acid
			| PubChem =1178
⚫	}}
			| ChEBI_Ref = {{ebicite|changed|EBI}}
	|Section2= {{Chembox Properties
			| ChEBI = 30817
⚫	| Formula=C<sub>6</sub>H<sub>6</sub>N<sub>2</sub>O<sub>2</sub>
		⚫	| MeSHName =Urocanic+acid
⚫	| MolarMass=138.124 g/mol
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| Appearance=
			| ChemSpiderID = 643824
	| Density=
		⚫	| SMILES = c1c(nc1)/C=C/C(=O)O
	| MeltingPt=225°C
			| InChI = 1/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
	| BoilingPt=
			| InChIKey = LOIYMIARKYCTBW-OWOJBTEDBA
	| Solubility=
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = LOIYMIARKYCTBW-OWOJBTEDSA-N
	}}		}}
	|Section3= {{Chembox Hazards		|Section2={{Chembox Properties
		⚫	| Formula =C<sub>6</sub>H<sub>6</sub>N<sub>2</sub>O<sub>2</sub>
	| MainHazards=
		⚫	| MolarMass =138.124 g/mol
	| FlashPt=
			| Appearance =
	| Autoignition=
			| Density =
			| MeltingPtC = 225
			| BoilingPt =
			| Solubility =
	}}		}}
			|Section3={{Chembox Hazards
			| MainHazards =
			| FlashPt =
			| AutoignitionPt =
		⚫	}}
	}}		}}
	'''Urocanic acid''' is an intermediate in the ] of <small>L</small>-].		'''Urocanic acid''' (formally '''''trans''-Urocanic acid''') is an intermediate in the ] of <small>L</small>-]. The ] isomer is rare.
	==Metabolism==		==Metabolism==
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	Inherited deficiency of urocanase leads to elevated levels of urocanic acid in the urine, a condition known as ].		Inherited deficiency of urocanase leads to elevated levels of urocanic acid in the urine, a condition known as ].
			An important role for the onset of ] and asthma has been attributed to ], a skin precursor of urocanic acid.<ref>{{cite journal | vauthors = Park KD, Pak SC, Park KK | title = The Pathogenetic Effect of Natural and Bacterial Toxins on Atopic Dermatitis | journal = Toxins | volume = 9 | issue = 1 | pages = 3 | date = December 2016 | pmid = 28025545 | pmc = 5299398 | doi = 10.3390/toxins9010003 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Irvine AD, McLean WH, Leung DY | title = Filaggrin mutations associated with skin and allergic diseases | journal = The New England Journal of Medicine | volume = 365 | issue = 14 | pages = 1315–27 | date = October 2011 | pmid = 21991953 | doi = 10.1056/nejmra1011040 }}</ref>
⚫	==Function==
	Urocanic acid was detected in animal sweat and skin where, among other possible functions, it acts as an endogenous sunscreen or photoprotectant against ]-induced DNA damage. Urocanic acid is found predominantly in the ] of the skin and it is likely that most of it is derived from ] catabolism (a histidine-rich protein). When exposed to UVB irradiation, trans-urocanic acid is converted ''in vitro'' and ''in vivo'' to the cis isomer. The cis form is known to activate ].
			Urocanic acid is thought to be a significant attractant of the nematode parasite '']'',<ref>{{Cite journal|doi=10.1073/pnas.0610193104|title=Urocanic acid is a major chemoattractant for the skin-penetrating parasitic nematode Strongyloides stercoralis|year=2007|last1=Safer|first1=D.|last2=Brenes|first2=M.|last3=Dunipace|first3=S.|last4=Schad|first4=G.|journal=Proceedings of the National Academy of Sciences|volume=104|issue=5|pages=1627–1630|pmid=17234810|pmc=1785286|doi-access=free}}</ref> in part because of relatively high levels in the plantar surfaces of the feet, the site through which this parasite often enters the body.
		⚫	== Function ==
			Urocanic acid was detected in animal sweat and skin where, among other possible functions, it acts as an endogenous sunscreen or photoprotectant against ]-induced DNA damage. Urocanic acid is found predominantly in the ] of the skin and it is likely that most of it is derived from filaggrin catabolism (a histidine-rich protein). When exposed to UVB irradiation, trans-urocanic acid is converted ''in vitro'' and ''in vivo'' to ] (cis-UCA).<ref name="pmid20442934">{{cite journal | vauthors = Egawa M, Nomura J, Iwaki H | title = The evaluation of the amount of cis- and trans-urocanic acid in the stratum corneum by Raman spectroscopy | journal = Photochemical and Photobiological Sciences | volume = 9 | issue = 5 | pages = 730–3 | date = May 2010 | pmid = 20442934 | doi = 10.1039/b9pp00143c | doi-access = free }}</ref> The cis form is known to activate ].<ref name="pmid16452825">{{cite journal | vauthors = Schwarz T | title = Mechanisms of UV-induced immunosuppression | journal = The Keio Journal of Medicine | volume = 54 | issue = 4 | pages = 165–71 | date = December 2005 | pmid = 16452825 | doi = 10.2302/kjm.54.165| url = http://www.kjm.keio.ac.jp/past/54/4/165.pdf | doi-access = free }}</ref>
			Some studies attribute filaggrin an important role in keeping the skin surface slightly acidic, through a breaking down mechanism to form histidine and subsequently trans-urocanic acid,<ref>{{cite journal | vauthors = Jungersted JM, Scheer H, Mempel M, Baurecht H, Cifuentes L, Høgh JK, Hellgren LI, Jemec GB, Agner T, Weidinger S | title = Stratum corneum lipids, skin barrier function and filaggrin mutations in patients with atopic eczema | journal = Allergy | volume = 65 | issue = 7 | pages = 911–8 | date = July 2010 | pmid = 20132155 | doi = 10.1111/j.1398-9995.2010.02326.x | s2cid = 24679127 }}</ref> however others have shown that the filaggrin–histidine–urocanic acid cascade is not essential for skin acidification.<ref>{{cite journal | vauthors = Fluhr JW, Elias PM, Man MQ, Hupe M, Selden C, Sundberg JP, Tschachler E, Eckhart L, Mauro TM, Feingold KR | title = Is the filaggrin-histidine-urocanic acid pathway essential for stratum corneum acidification? | journal = The Journal of Investigative Dermatology | volume = 130 | issue = 8 | pages = 2141–4 | date = August 2010 | pmid = 20376063 | pmc = 4548931 | doi = 10.1038/jid.2010.74 }}</ref>
	==History==		==History==
	Urocanic acid was first isolated in 1874 by the chemist M. Jaffé from the urine of a dog,<ref>{{cite journal | last1 = Jaffé | first1 = M. | year = 1874 | title = Concerning a new constituent in the urine of dogs | url = | journal = Ber. Deut. Chem. Ges. | volume = 7 | issue = | pages = 1669–1673 }}</ref> hence the name ({{lang-la|urina}} = urine, and ''canis'' = dog).		Urocanic acid was first isolated in 1874 by the chemist ] from the urine of a dog,<ref>{{cite journal | vauthors = Jaffe M | doi = 10.1002/cber.187500801267 | title = Ueber die Urocaninsäure | trans-title = About urocanic acid | language = German | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 8 | issue = 1 | date = 1875 | pages = 811–813 | url = https://zenodo.org/record/1425082 }}</ref><ref name = "Jaffe_1874">{{cite journal | vauthors = Jaffe M | doi = 10.1002/cber.187400702225 | title = Ueber einen neuen Bestandtheil des Hundeharns | trans-title = Concerning a new constituent in the urine of dogs | language = German | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 7 | issue = 2 | date = 1874 | pages = 1669–1673 | url = https://zenodo.org/record/1425064 }}</ref> hence the name ({{langx|la|urina}} = urine, and ''canis'' = dog).
	==See also==		== See also ==
			* ]
	* ]		* ]
	==References==		== References ==
			{{reflist|32em}}
	<references/>
	==External links==		== External links ==
	* - An overview of disorders of histidine metabolism, including urocanic aciduria.		* - An overview of disorders of histidine metabolism, including urocanic aciduria.
	{{Amino acid metabolism intermediates}}		{{Amino acid metabolism intermediates}}
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