Stable homotopy theory - Revision history

en>Trappist the monk: /* References */replace mr template with mr parameter in CS1 templates; using AWB

2014-09-25T22:15:43Z

References: replace mr template with mr parameter in CS1 templates; using AWB

← Older revision		Revision as of 00:15, 26 September 2014
Line 1:		Line 1:
	~~{{chembox~~		The author's title is Christy. To perform domino is some thing I truly appreciate performing. North Carolina is the location he enjoys most but now [http://cpacs.org/index.php?document_srl=90091&mid=board_zTGg26 tarot readings] he is contemplating other choices. Distributing manufacturing is exactly where my primary income arrives from and it's something I really appreciate.<br><br>Feel free [http://www.zavodpm.ru/blogs/glennmusserrvji/14565-great-hobby-advice-assist-allow-you-get-going free psychic readings] to surf to my web blog: clairvoyant psychic ([http://myfusionprofits.com/groups/find-out-about-self-improvement-tips-here/ http://myfusionprofits.com])
	~~\| verifiedrevid = 443847685~~
	~~\| Name = Glyoxylic acid~~
	~~\| ImageFile_Ref = {{chemboximage\|correct\|??}}~~
	~~\| ImageFile = Glyoxylic acid.png~~
	~~\| ImageSize = 150px~~
	~~\| ImageName = Structure of glyoxylic acid~~
	~~\| ImageFile1 = Glyoxylic-acid-3D-balls.png~~
	~~\| ImageSize1 = 160px~~
	~~\| ImageName1 = Ball-and-stick model of glyoxylic acid~~
	~~\| IUPACName = oxoethanoic acid~~
	~~\| OtherNames = formylformic acid; oxoethanoic acid~~
	~~\| Section1 = {{Chembox Identifiers~~
	~~\| PubChem = 760~~
	~~\| KEGG_Ref = {{keggcite\|correct\|kegg}}~~
	~~\| KEGG = C00048~~
	~~\| InChI = 1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)~~
	~~\| InChIKey = HHLFWLYXYJOTON-UHFFFAOYAU~~
	~~\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}~~
	~~\| ChEMBL = 1162545~~
	~~\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}~~
	~~\| StdInChI = 1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)~~
	~~\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}~~
	~~\| StdInChIKey = HHLFWLYXYJOTON-UHFFFAOYSA-N~~
	~~\| CASNo_Ref = {{cascite\|correct\|CAS}}~~
	~~\| CASNo = 298-12-4~~
	~~\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}~~
	~~\| ChemSpiderID = 740~~
	~~\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}~~
	~~\| DrugBank = DB04343~~
	~~\| ChEBI_Ref = {{ebicite\|correct\|EBI}}~~
	~~\| ChEBI = 16891~~
	~~\| SMILES = C(=O)C(=O)O~~
	}}
	~~\| Section2 = {{Chembox Properties~~
	~~\| C=2\|H=2\|O=3~~
	~~\| MeltingPt = 80 °C<ref name=Merck>''[[Merck Index]], 11th Edition, '''4394''~~'~~</ref>~~
	~~\| BoilingPt = 111 °C~~
	~~\| Density = 1.384 g/mL~~
	\| pKa = 3.18,<ref>Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.</ref> 3.32 <ref>pKa Data Compiled by R. Williams, http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf.</ref>
	}}
	~~\| Section4 = {{Chembox Related~~
	~~\| OtherAnions = [[glyoxylate]]~~
	~~\| Function = [[carboxylic acid]]~~s
	~~\| OtherFunctn = [[formic acid]]<br />[[acetic acid]]<br />[[glycolic acid]]<br />[[oxalic acid]]<br />[[propionic acid]]<br />[[pyruvic acid]]~~
	~~\| OtherCpds = [[acetaldehyde]]<br />[[glyoxal]]<br />[[glycolaldehyde]]~~
	}}
	}}

	'''Glyoxylic acid''' or '''oxoacetic acid''' is an [[organic compound]]. Together with [[acetic acid]], [[glycolic acid]], and [[oxalic acid]], glyoxylic acid is one of the C<sub>2</sub> [[carboxylic acid]]s. It is a colourless solid that occurs naturally and is useful industrially.

	~~==Structure and nomenclature==~~
	~~Glyoxylic acid~~ is ~~usually described with the [[chemical formula]] OCHCO<sub>2</sub>H, i.e~~. ~~containing an [[aldehyde]] [[functional group]] (see image in upper right). In fact the aldehyde~~ is ~~not observed in solution or as a solid~~. ~~In general aldehydes with electron-withdrawing substituents often exist mainly as their hydrate. Thus, the formula for glyoxylic acid~~ is ~~really (HO)<sub>2</sub>CHCO<sub>2</sub>H, described as~~ the ~~"monohydrate."~~ ~~This~~ [~~[diol]] exists in equilibrium with the dimeric hemiacetal in solution~~:~~<ref name=Ull>Georges Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{DOI\|10.1002~~/~~14356007.a12_495}}<~~/~~ref> Henry's law constant of glyoxylic acid is K<sub>H</sub> = 1~~.~~09 × 10<sup>4<~~/~~sup> × exp[(40~~.~~0 × 10<sup>3</sup>/R) × (1/T − 1/298)].<ref>{{cite journal\|last~~=Ip\|first=H. S. Simon\|coauthors=Huang, X. H. Hilda, Yu, Jian Zhen\|title=Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid\|journal=Geophysical Research Letters\|volume=36\|issue=1\|doi=10.1029/2008GL036212}}</ref>
	~~:2 (HO)<sub>2</sub>CHCO<sub>2</sub>H <math>\overrightarrow{\leftarrow}</math> O[(HO)CHCO<sub>2</sub>H]<sub>2</sub> + H<sub>2</sub>O~~

	~~==Preparation~~==
	~~The compound is formed by [[organic oxidation]] of [[glyoxal]] with hot [[nitric acid]], the main side product being oxalic acid. [[Ozonolysis]] of [[maleic acid]~~] is ~~also effective~~.~~<ref name=Ull/>~~

	~~The [[conjugate base]] of gloxylic acid~~ is ~~known as glyoxylate~~ and ~~is the form that the compound exists in solution at neutral pH. Glyoxylate is an intermediate of the [[glyoxylate cycle]], which enables [[organism]]~~s~~, such as bacteria,<ref name="Holms">{{cite journal\|author=Holms WH\|year=1987\|title=Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli\|journal=Biochem Soc Symp~~.~~\|volume=54\|pages=17–31\|pmid=3332993}}~~<~~/ref~~> ~~fungi, and plants~~ <~~ref name="Escher and Widmer F"~~>{{cite journal\|author=Escher CL, Widmer F\|year=1997\|title=Lipid mobilization and gluconeogenesis in plants: do glyoxylate cycle enzyme activities constitute a real cycle? A hypothesis\|journal=Biol Chem.\|volume=378\|pages=803–813\|pmid=9377475\|issue=8}}</ref> to convert [[fatty acid]]s into [[carbohydrate]]s. ~~Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.~~

	~~Historically glyoxylic acid was prepared from oxalic acid~~ [[Electrosynthesis\|electrosynthetically]].<ref>{{cite journal\|last=Tafel, Julius; and Friedrichs, Gustav\|title=Elektrolytische Reduction von Carbonsäuren und Carbonsäureestern in schwefelsaurer Lösung\|journal=Berichte der deutschen chemischen Gesellschaft\|year=1904\|volume=37\|issue=3\|pages=3187-3191\|doi=10.1002/cber.190403703116\|url=http://~~onlinelibrary~~.~~wiley~~.~~com~~/~~doi~~/~~10.1002~~/cber.190403703116/abstract\|accessdate=19 December 2013}}</ref><ref>{{cite book\|last=Cohen\|first=Julius\|title=Practical Organic Chemistry 2nd Ed.\|year=1920\|publisher=Macmillan and Co. Limited\|location=London\|pages=102-~~104\|url=http://www.sciencemadness.org/library/books/practical_organic_chemistry.pdf}}</ref>~~

	~~==Reactions and uses==~~
	~~Glyoxylic acid is about 10x stronger acid than acetic acid, with an [[acid dissociation constant]] of 4.7 × 10<sup>−4</sup> (pK<sub>a</sub> = 3.32):~~
	~~:(HO)<sub>2</sub>CHCOOH <math>\overrightarrow{\leftarrow}</math> (HO)<sub>2</sub>CHCO<sub>2</sub><sup>−</sup> + H<sup>+</sup>~~
	~~With base, glyoxylic acid [[disproportionation\|disproportionates]]:~~
	~~:2 OCHCOOH + H<sub>2</sub>O → HOCHCOOH + HOOC–COOH~~

	Even though the aldehyde is a very minor component of its solutions, glyoxylic acid behaves as an aldehyde in its reactions. For example, it gives heterocycles upon [[condensation reaction\|condensation]] with [[urea]] and [[1,2-~~diaminobenzene]].~~

	~~===Phenol derivatives===~~
	~~Its condensation with phenols is versatile. The immediate product is 4~~-~~hydroxy[[mandelic acid]]. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug [[Amoxicillin]]. Reduction of the 4~~-~~hydroxymandelic acid gives [[4~~-~~hydroxyphenylacetic acid~~]~~], a precursor~~ to ~~the drug [[Atenolol]]. Condensations with [[guaiacol]] in place of phenol provides a route~~ to [~~[vanillin]], a net [[formylation]]~~.~~<ref name=Ull~~/~~><ref>{{cite journal\|last=Fatiadi, Alexander; and Schaffer, Robert\|title=An Improved Procedure for Synthesis of~~
	DL-4-~~Hydroxy~~-3-~~methoxymandelic Acid (DL~~-~~"Vanillyl"-mandelic Acid, VMA)\|journal=Journal of Research of the National Bureau of Standards~~ - ~~A. Physics and Chemistry\|year=1974\|volume=78A\|issue=3\|pages=411-412\|doi=10.6028~~/~~jres.078A.024\|url=~~http://nvlpubs.nist.gov/nistpubs/jres/78A/jresv78An3p411_A1b.pdf\|accessdate=19 December 2013}}</ref><ref>{{cite book\|last=Kamlet, Jonas; and Mathieson, Olin\|title=Manufacture of vanillin and its homologues U.S. Patent 2,640,083\|year=1953\|publisher=U.S. Patent Office\|url=https://docs.google.com~~/viewer?url=patentimages.storage.googleapis.com/pdfs/US2640083.pdf}}</ref>~~

	~~==Safety==~~
	~~The compound is not very toxic with an {{LD50}} for rats of 2500 mg/kg.~~

	~~==References==~~
	~~<references/>~~

	~~[[Category:Carboxylic acids]]~~
	~~[[Category:Aldehydes]~~]

en>ChrisGualtieri: /* References */Remove stub template(s). Page is start class or higher. Also check for and do General Fixes + Checkwiki fixes using AWB

2013-12-13T02:53:25Z

References: Remove stub template(s). Page is start class or higher. Also check for and do General Fixes + Checkwiki fixes using AWB

← Older revision		Revision as of 04:53, 13 December 2013
Line 1:		Line 1:
	~~Greetings! I am [http:~~//~~goaskalice.Columbia.edu~~/~~what~~-do-~~genital~~-~~warts~~-~~look Marvella~~] and ~~I feel comfortable when people use the [~~http://~~www~~.~~dynast~~.co.kr/xe/~~?document_srl~~=~~150618 extra resources~~] ~~complete name~~. ~~Puerto Rico~~ is ~~where he'~~s usually ~~been residing but she requirements to move simply because of her family members~~. ~~His wife doesn't like it~~ the ~~std testing at home std testing at home way he does~~ [~~http~~://~~3bbc~~.~~com~~/~~index~~.~~php?do~~=/~~profile-548128~~/~~info~~/ ~~at home std testing~~] ~~but what he really likes performing~~ is ~~to do aerobics~~ and ~~he'~~s ~~been performing it for quite~~ a ~~whilst~~. My ~~at home std test working day job~~ is a [http://~~Www~~.~~myelectronicmd~~.com/~~get_reference~~.~~php?Id~~=~~1296~~&~~condition=ANAL%20HERPES%20SIMPLEX%20VIRUS~~&~~symname=A~~&~~typ~~=3 ~~librarian]~~.<br><br>~~My web site~~: ~~over~~ the ~~counter std test~~ ([http://~~musical~~.~~sehan~~.ac.kr/?~~document_srl~~=~~2110508 please click the following post~~])		{{chembox
			\| verifiedrevid = 443847685
			\| Name = Glyoxylic acid
			\| ImageFile_Ref = {{chemboximage\|correct\|??}}
			\| ImageFile = Glyoxylic acid.png
			\| ImageSize = 150px
			\| ImageName = Structure of glyoxylic acid
			\| ImageFile1 = Glyoxylic-acid-3D-balls.png
			\| ImageSize1 = 160px
			\| ImageName1 = Ball-and-stick model of glyoxylic acid
			\| IUPACName = oxoethanoic acid
			\| OtherNames = formylformic acid; oxoethanoic acid
			\| Section1 = {{Chembox Identifiers
			\| PubChem = 760
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
			\| KEGG = C00048
			\| InChI = 1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
			\| InChIKey = HHLFWLYXYJOTON-UHFFFAOYAU
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
			\| ChEMBL = 1162545
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
			\| StdInChI = 1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
			\| StdInChIKey = HHLFWLYXYJOTON-UHFFFAOYSA-N
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| CASNo = 298-12-4
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID = 740
			\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
			\| DrugBank = DB04343
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
			\| ChEBI = 16891
			\| SMILES = C(=O)C(=O)O
			}}
			\| Section2 = {{Chembox Properties
			\| C=2\|H=2\|O=3
			\| MeltingPt = 80 °C<ref name=Merck>''[[Merck Index]], 11th Edition, '''4394'''</ref>
			\| BoilingPt = 111 °C
			\| Density = 1.384 g/mL
			\| pKa = 3.18,<ref>Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.</ref> 3.32 <ref>pKa Data Compiled by R. Williams, http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf.</ref>
			}}
			\| Section4 = {{Chembox Related
			\| OtherAnions = [[glyoxylate]]
			\| Function = [[carboxylic acid]]s
			\| OtherFunctn = [[formic acid]]<br />[[acetic acid]]<br />[[glycolic acid]]<br />[[oxalic acid]]<br />[[propionic acid]]<br />[[pyruvic acid]]
			\| OtherCpds = [[acetaldehyde]]<br />[[glyoxal]]<br />[[glycolaldehyde]]
			}}
			}}

			'''Glyoxylic acid''' or '''oxoacetic acid''' is an [[organic compound]]. Together with [[acetic acid]], [[glycolic acid]], and [[oxalic acid]], glyoxylic acid is one of the C<sub>2</sub> [[carboxylic acid]]s. It is a colourless solid that occurs naturally and is useful industrially.

			==Structure and nomenclature==
			Glyoxylic acid is usually described with the [[chemical formula]] OCHCO<sub>2</sub>H, i.e. containing an [[aldehyde]] [[functional group]] (see image in upper right). In fact the aldehyde is not observed in solution or as a solid. In general aldehydes with electron-withdrawing substituents often exist mainly as their hydrate. Thus, the formula for glyoxylic acid is really (HO)<sub>2</sub>CHCO<sub>2</sub>H, described as the "monohydrate." This [[diol]] exists in equilibrium with the dimeric hemiacetal in solution:<ref name=Ull>Georges Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{DOI\|10.1002/14356007.a12_495}}</ref> Henry's law constant of glyoxylic acid is K<sub>H</sub> = 1.09 × 10<sup>4</sup> × exp[(40.0 × 10<sup>3</sup>/R) × (1/T − 1/298)].<ref>{{cite journal\|last=Ip\|first=H. S. Simon\|coauthors=Huang, X. H. Hilda, Yu, Jian Zhen\|title=Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid\|journal=Geophysical Research Letters\|volume=36\|issue=1\|doi=10.1029/2008GL036212}}</ref>
			:2 (HO)<sub>2</sub>CHCO<sub>2</sub>H <math>\overrightarrow{\leftarrow}</math> O[(HO)CHCO<sub>2</sub>H]<sub>2</sub> + H<sub>2</sub>O

			==Preparation==
			The compound is formed by [[organic oxidation]] of [[glyoxal]] with hot [[nitric acid]], the main side product being oxalic acid. [[Ozonolysis]] of [[maleic acid]] is also effective.<ref name=Ull/>

			The [[conjugate base]] of gloxylic acid is known as glyoxylate and is the form that the compound exists in solution at neutral pH. Glyoxylate is an intermediate of the [[glyoxylate cycle]], which enables [[organism]]s, such as bacteria,<ref name="Holms">{{cite journal\|author=Holms WH\|year=1987\|title=Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli\|journal=Biochem Soc Symp.\|volume=54\|pages=17–31\|pmid=3332993}}</ref> fungi, and plants <ref name="Escher and Widmer F">{{cite journal\|author=Escher CL, Widmer F\|year=1997\|title=Lipid mobilization and gluconeogenesis in plants: do glyoxylate cycle enzyme activities constitute a real cycle? A hypothesis\|journal=Biol Chem.\|volume=378\|pages=803–813\|pmid=9377475\|issue=8}}</ref> to convert [[fatty acid]]s into [[carbohydrate]]s. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.

			Historically glyoxylic acid was prepared from oxalic acid [[Electrosynthesis\|electrosynthetically]].<ref>{{cite journal\|last=Tafel, Julius; and Friedrichs, Gustav\|title=Elektrolytische Reduction von Carbonsäuren und Carbonsäureestern in schwefelsaurer Lösung\|journal=Berichte der deutschen chemischen Gesellschaft\|year=1904\|volume=37\|issue=3\|pages=3187-3191\|doi=10.1002/cber.190403703116\|url=http://onlinelibrary.wiley.com/doi/10.1002/cber.190403703116/abstract\|accessdate=19 December 2013}}</ref><ref>{{cite book\|last=Cohen\|first=Julius\|title=Practical Organic Chemistry 2nd Ed.\|year=1920\|publisher=Macmillan and Co. Limited\|location=London\|pages=102-104\|url=http://www.sciencemadness.org/library/books/practical_organic_chemistry.pdf}}</ref>

			==Reactions and uses==
			Glyoxylic acid is about 10x stronger acid than acetic acid, with an [[acid dissociation constant]] of 4.7 × 10<sup>−4</sup> (pK<sub>a</sub> = 3.32):
			:(HO)<sub>2</sub>CHCOOH <math>\overrightarrow{\leftarrow}</math> (HO)<sub>2</sub>CHCO<sub>2</sub><sup>−</sup> + H<sup>+</sup>
			With base, glyoxylic acid [[disproportionation\|disproportionates]]:
			:2 OCHCOOH + H<sub>2</sub>O → HOCHCOOH + HOOC–COOH

			Even though the aldehyde is a very minor component of its solutions, glyoxylic acid behaves as an aldehyde in its reactions. For example, it gives heterocycles upon [[condensation reaction\|condensation]] with [[urea]] and [[1,2-diaminobenzene]].

			===Phenol derivatives===
			Its condensation with phenols is versatile. The immediate product is 4-hydroxy[[mandelic acid]]. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug [[Amoxicillin]]. Reduction of the 4-hydroxymandelic acid gives [[4-hydroxyphenylacetic acid]], a precursor to the drug [[Atenolol]]. Condensations with [[guaiacol]] in place of phenol provides a route to [[vanillin]], a net [[formylation]].<ref name=Ull/><ref>{{cite journal\|last=Fatiadi, Alexander; and Schaffer, Robert\|title=An Improved Procedure for Synthesis of
			DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)\|journal=Journal of Research of the National Bureau of Standards - A. Physics and Chemistry\|year=1974\|volume=78A\|issue=3\|pages=411-412\|doi=10.6028/jres.078A.024\|url=http://nvlpubs.nist.gov/nistpubs/jres/78A/jresv78An3p411_A1b.pdf\|accessdate=19 December 2013}}</ref><ref>{{cite book\|last=Kamlet, Jonas; and Mathieson, Olin\|title=Manufacture of vanillin and its homologues U.S. Patent 2,640,083\|year=1953\|publisher=U.S. Patent Office\|url=https://docs.google.com/viewer?url=patentimages.storage.googleapis.com/pdfs/US2640083.pdf}}</ref>

			==Safety==
			The compound is not very toxic with an {{LD50}} for rats of 2500 mg/kg.

			==References==
			<references/>

			[[Category:Carboxylic acids]]
			[[Category:Aldehydes]]

en>Jakob.scholbach: /* References */ polish

2010-04-29T15:17:05Z

References: polish

New page

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← Older revision		Revision as of 00:15, 26 September 2014
Line 1:		Line 1:
	~~{{chembox~~		The author's title is Christy. To perform domino is some thing I truly appreciate performing. North Carolina is the location he enjoys most but now [http://cpacs.org/index.php?document_srl=90091&mid=board_zTGg26 tarot readings] he is contemplating other choices. Distributing manufacturing is exactly where my primary income arrives from and it's something I really appreciate.<br><br>Feel free [http://www.zavodpm.ru/blogs/glennmusserrvji/14565-great-hobby-advice-assist-allow-you-get-going free psychic readings] to surf to my web blog: clairvoyant psychic ([http://myfusionprofits.com/groups/find-out-about-self-improvement-tips-here/ http://myfusionprofits.com])
	~~\| verifiedrevid = 443847685~~
	~~\| Name = Glyoxylic acid~~
	~~\| ImageFile_Ref = {{chemboximage\|correct\|??}}~~
	~~\| ImageFile = Glyoxylic acid.png~~
	~~\| ImageSize = 150px~~
	~~\| ImageName = Structure of glyoxylic acid~~
	~~\| ImageFile1 = Glyoxylic-acid-3D-balls.png~~
	~~\| ImageSize1 = 160px~~
	~~\| ImageName1 = Ball-and-stick model of glyoxylic acid~~
	~~\| IUPACName = oxoethanoic acid~~
	~~\| OtherNames = formylformic acid; oxoethanoic acid~~
	~~\| Section1 = {{Chembox Identifiers~~
	~~\| PubChem = 760~~
	~~\| KEGG_Ref = {{keggcite\|correct\|kegg}}~~
	~~\| KEGG = C00048~~
	~~\| InChI = 1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)~~
	~~\| InChIKey = HHLFWLYXYJOTON-UHFFFAOYAU~~
	~~\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}~~
	~~\| ChEMBL = 1162545~~
	~~\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}~~
	~~\| StdInChI = 1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)~~
	~~\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}~~
	~~\| StdInChIKey = HHLFWLYXYJOTON-UHFFFAOYSA-N~~
	~~\| CASNo_Ref = {{cascite\|correct\|CAS}}~~
	~~\| CASNo = 298-12-4~~
	~~\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}~~
	~~\| ChemSpiderID = 740~~
	~~\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}~~
	~~\| DrugBank = DB04343~~
	~~\| ChEBI_Ref = {{ebicite\|correct\|EBI}}~~
	~~\| ChEBI = 16891~~
	~~\| SMILES = C(=O)C(=O)O~~
	}}
	~~\| Section2 = {{Chembox Properties~~
	~~\| C=2\|H=2\|O=3~~
	~~\| MeltingPt = 80 °C<ref name=Merck>''[[Merck Index]], 11th Edition, '''4394''~~'~~</ref>~~
	~~\| BoilingPt = 111 °C~~
	~~\| Density = 1.384 g/mL~~
	\| pKa = 3.18,<ref>Dissociation Constants Of Organic Acids and Bases (600 compounds), http://zirchrom.com/organic.htm.</ref> 3.32 <ref>pKa Data Compiled by R. Williams, http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf.</ref>
	}}
	~~\| Section4 = {{Chembox Related~~
	~~\| OtherAnions = [[glyoxylate]]~~
	~~\| Function = [[carboxylic acid]]~~s
	~~\| OtherFunctn = [[formic acid]]<br />[[acetic acid]]<br />[[glycolic acid]]<br />[[oxalic acid]]<br />[[propionic acid]]<br />[[pyruvic acid]]~~
	~~\| OtherCpds = [[acetaldehyde]]<br />[[glyoxal]]<br />[[glycolaldehyde]]~~
	}}
	}}

	'''Glyoxylic acid''' or '''oxoacetic acid''' is an [[organic compound]]. Together with [[acetic acid]], [[glycolic acid]], and [[oxalic acid]], glyoxylic acid is one of the C<sub>2</sub> [[carboxylic acid]]s. It is a colourless solid that occurs naturally and is useful industrially.

	~~==Structure and nomenclature==~~
	~~Glyoxylic acid~~ is ~~usually described with the [[chemical formula]] OCHCO<sub>2</sub>H, i.e~~. ~~containing an [[aldehyde]] [[functional group]] (see image in upper right). In fact the aldehyde~~ is ~~not observed in solution or as a solid~~. ~~In general aldehydes with electron-withdrawing substituents often exist mainly as their hydrate. Thus, the formula for glyoxylic acid~~ is ~~really (HO)<sub>2</sub>CHCO<sub>2</sub>H, described as~~ the ~~"monohydrate."~~ ~~This~~ [~~[diol]] exists in equilibrium with the dimeric hemiacetal in solution~~:~~<ref name=Ull>Georges Mattioda and Yani Christidis “Glyoxylic Acid” Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{DOI\|10.1002~~/~~14356007.a12_495}}<~~/~~ref> Henry's law constant of glyoxylic acid is K<sub>H</sub> = 1~~.~~09 × 10<sup>4<~~/~~sup> × exp[(40~~.~~0 × 10<sup>3</sup>/R) × (1/T − 1/298)].<ref>{{cite journal\|last~~=Ip\|first=H. S. Simon\|coauthors=Huang, X. H. Hilda, Yu, Jian Zhen\|title=Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid\|journal=Geophysical Research Letters\|volume=36\|issue=1\|doi=10.1029/2008GL036212}}</ref>
	~~:2 (HO)<sub>2</sub>CHCO<sub>2</sub>H <math>\overrightarrow{\leftarrow}</math> O[(HO)CHCO<sub>2</sub>H]<sub>2</sub> + H<sub>2</sub>O~~

	~~==Preparation~~==
	~~The compound is formed by [[organic oxidation]] of [[glyoxal]] with hot [[nitric acid]], the main side product being oxalic acid. [[Ozonolysis]] of [[maleic acid]~~] is ~~also effective~~.~~<ref name=Ull/>~~

	~~The [[conjugate base]] of gloxylic acid~~ is ~~known as glyoxylate~~ and ~~is the form that the compound exists in solution at neutral pH. Glyoxylate is an intermediate of the [[glyoxylate cycle]], which enables [[organism]]~~s~~, such as bacteria,<ref name="Holms">{{cite journal\|author=Holms WH\|year=1987\|title=Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli\|journal=Biochem Soc Symp~~.~~\|volume=54\|pages=17–31\|pmid=3332993}}~~<~~/ref~~> ~~fungi, and plants~~ <~~ref name="Escher and Widmer F"~~>{{cite journal\|author=Escher CL, Widmer F\|year=1997\|title=Lipid mobilization and gluconeogenesis in plants: do glyoxylate cycle enzyme activities constitute a real cycle? A hypothesis\|journal=Biol Chem.\|volume=378\|pages=803–813\|pmid=9377475\|issue=8}}</ref> to convert [[fatty acid]]s into [[carbohydrate]]s. ~~Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.~~

	~~Historically glyoxylic acid was prepared from oxalic acid~~ [[Electrosynthesis\|electrosynthetically]].<ref>{{cite journal\|last=Tafel, Julius; and Friedrichs, Gustav\|title=Elektrolytische Reduction von Carbonsäuren und Carbonsäureestern in schwefelsaurer Lösung\|journal=Berichte der deutschen chemischen Gesellschaft\|year=1904\|volume=37\|issue=3\|pages=3187-3191\|doi=10.1002/cber.190403703116\|url=http://~~onlinelibrary~~.~~wiley~~.~~com~~/~~doi~~/~~10.1002~~/cber.190403703116/abstract\|accessdate=19 December 2013}}</ref><ref>{{cite book\|last=Cohen\|first=Julius\|title=Practical Organic Chemistry 2nd Ed.\|year=1920\|publisher=Macmillan and Co. Limited\|location=London\|pages=102-~~104\|url=http://www.sciencemadness.org/library/books/practical_organic_chemistry.pdf}}</ref>~~

	~~==Reactions and uses==~~
	~~Glyoxylic acid is about 10x stronger acid than acetic acid, with an [[acid dissociation constant]] of 4.7 × 10<sup>−4</sup> (pK<sub>a</sub> = 3.32):~~
	~~:(HO)<sub>2</sub>CHCOOH <math>\overrightarrow{\leftarrow}</math> (HO)<sub>2</sub>CHCO<sub>2</sub><sup>−</sup> + H<sup>+</sup>~~
	~~With base, glyoxylic acid [[disproportionation\|disproportionates]]:~~
	~~:2 OCHCOOH + H<sub>2</sub>O → HOCHCOOH + HOOC–COOH~~

	Even though the aldehyde is a very minor component of its solutions, glyoxylic acid behaves as an aldehyde in its reactions. For example, it gives heterocycles upon [[condensation reaction\|condensation]] with [[urea]] and [[1,2-~~diaminobenzene]].~~

	~~===Phenol derivatives===~~
	~~Its condensation with phenols is versatile. The immediate product is 4~~-~~hydroxy[[mandelic acid]]. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug [[Amoxicillin]]. Reduction of the 4~~-~~hydroxymandelic acid gives [[4~~-~~hydroxyphenylacetic acid~~]~~], a precursor~~ to ~~the drug [[Atenolol]]. Condensations with [[guaiacol]] in place of phenol provides a route~~ to [~~[vanillin]], a net [[formylation]]~~.~~<ref name=Ull~~/~~><ref>{{cite journal\|last=Fatiadi, Alexander; and Schaffer, Robert\|title=An Improved Procedure for Synthesis of~~
	DL-4-~~Hydroxy~~-3-~~methoxymandelic Acid (DL~~-~~"Vanillyl"-mandelic Acid, VMA)\|journal=Journal of Research of the National Bureau of Standards~~ - ~~A. Physics and Chemistry\|year=1974\|volume=78A\|issue=3\|pages=411-412\|doi=10.6028~~/~~jres.078A.024\|url=~~http://nvlpubs.nist.gov/nistpubs/jres/78A/jresv78An3p411_A1b.pdf\|accessdate=19 December 2013}}</ref><ref>{{cite book\|last=Kamlet, Jonas; and Mathieson, Olin\|title=Manufacture of vanillin and its homologues U.S. Patent 2,640,083\|year=1953\|publisher=U.S. Patent Office\|url=https://docs.google.com~~/viewer?url=patentimages.storage.googleapis.com/pdfs/US2640083.pdf}}</ref>~~

	~~==Safety==~~
	~~The compound is not very toxic with an {{LD50}} for rats of 2500 mg/kg.~~

	~~==References==~~
	~~<references/>~~

	~~[[Category:Carboxylic acids]]~~
	~~[[Category:Aldehydes]~~]