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Revision as of 10:27, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').← Previous edit		Latest revision as of 22:19, 20 December 2024 edit undoBernanke's Crossbow (talk | contribs)Extended confirmed users7,810 edits →Reactions and uses: polym
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			{{Short description|Acetic acid bearing an aldehyde group}}
	{{chembox		{{chembox
			|Watchedfields = changed
	| verifiedrevid = 415510077
			|verifiedrevid = 443847685
	| Name = Glyoxylic acid
			|Name = Glyoxylic acid
	| ImageFile_Ref = {{chemboximage|correct|??}}
			|ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile = Glyoxylic acid.png
			|ImageFile = Glyoxylic acid.png
	| ImageSize = 150px
			|ImageSize = 150px
	| ImageName = Structure of glyoxylic acid
			|ImageAlt = Skeletal formula of glyoxylic acid
	| ImageFile1 = Glyoxylic-acid-3D-balls.png
			|ImageFile1 = Glyoxylic acid 3D spacefill.png
	| ImageSize1 = 160px
			|ImageSize1 = 160px
	| ImageName1 = Ball-and-stick model of glyoxylic acid
			|ImageAlt1 = Space-filling model of glyoxylic acid
	| IUPACName = oxoethanoic acid
			|PIN = Oxoacetic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 748 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
	| OtherNames = formylformic acid; oxoethanoic acid
			|SystematicName = Oxoethanoic acid
	| Section1 = {{Chembox Identifiers
			|OtherNames = Glyoxylic acid<ref name=iupac2013/><br />2-Oxoacetic acid<br />Formylformic acid
	| PubChem = 760
			|Section1={{Chembox Identifiers
	| KEGG_Ref = {{keggcite|correct|kegg}}
			|CASNo_Ref = {{cascite|correct|CAS}}
	| KEGG = C00048
			|CASNo = 298-12-4
	| InChI = 1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
			|PubChem = 760
	| InChIKey = HHLFWLYXYJOTON-UHFFFAOYAU
			|Beilstein = 741891
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
			|ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 1162545
			|ChEBI = 16891
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| StdInChI = 1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
			|ChEMBL = 1162545
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| StdInChIKey = HHLFWLYXYJOTON-UHFFFAOYSA-N
			|ChemSpiderID = 740
	| CASNo_Ref = {{cascite|correct|CAS}}
			|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| CASNo = 298-12-4
			|DrugBank = DB04343
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|EINECS = 206-058-5
	| ChemSpiderID = 740
			|Gmelin = 25752
	| DrugBank = DB04343
			|KEGG_Ref = {{keggcite|correct|kegg}}
	| ChEBI = 16891
			|KEGG = C00048
	| SMILES = C(=O)C(=O)O
			|UNII_Ref = {{fdacite|correct|FDA}}
			|UNII = JQ39C92HH6
			|InChI = 1/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
			|InChIKey = HHLFWLYXYJOTON-UHFFFAOYAU
			|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
			|SMILES = C(=O)C(=O)O
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=2|H=2|O=3		|C=2 | H=2 | O=3
			|MeltingPtC = 80
	| MeltingPt = 80 °C<ref name=Merck>''], 11th Edition, '''4394'''</ref>
			|MeltingPt_ref = <ref name=Merck>''], 11th Edition, '''4394'''</ref>
	| BoilingPt = 111 °C
	| Density =		|BoilingPtC = 111
			|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, {{cite web |url=http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf |title=Archived copy |access-date=2010-06-02 |url-status=dead |archive-url=https://web.archive.org/web/20100602043012/http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf |archive-date=2010-06-02 }}.</ref>
			}}
			|Section3={{Chembox Related
			|OtherAnions = ]
			|OtherFunction_label = ]s
			|OtherFunction = ]<br />]<br />]<br />]<br />]<br />]
			|OtherCompounds = ]<br />]<br />]
	}}		}}
	| Section4 = {{Chembox Related
	| OtherAnions = ]
	| Function = ]s
	| OtherFunctn = ]<br />]<br />]<br />]<br />]<br />]
	| OtherCpds = ]<br />]<br />]
	}}
	}}		}}
	'''Glyoxylic acid''' or '''oxoacetic acid''' is an ]. Together with acetic acid, ], and oxalic acid, glyoxylic acid is one of the C<sub>2</sub> ]s. It is a colourless solid that occurs naturally and is useful industrially.		'''Glyoxylic acid''' or '''oxoacetic acid''' is an ]. Together with ], ], and ], glyoxylic acid is one of the C<sub>2</sub> ]s. It is a colourless solid that occurs naturally and is useful industrially.
	==Structure and nomenclature==		==Structure and nomenclature==
			The structure of glyoxylic acid is shown as having an ] ]. The aldehyde is only a minor component of the form most prevalent in some situations. Instead, glyoxalic acid often exists as a hydrate or a cyclic ]. For example, in the presence of water, the ] rapidly converts to a ] (described as the "monohydrate"). The ] (''K'') is 300 for the formation of '''dihydroxyacetic acid''' at room temperature:<ref>{{cite journal |last1= Sørensen |first1= P. E. |last2= Bruhn |first2= K. |last3= Lindeløv |first3= F. |title= Kinetics and equilibria for the reversible hydration of the aldehyde group in glyoxylic acid. |journal= Acta Chem. Scand. |year= 1974 |volume= 28 |pages= 162–168 |doi= 10.3891/acta.chem.scand.28a-0162 |doi-access= free }}</ref> Dihydroxyacetic acid has been characterized by ].<ref>{{cite journal |doi=10.1107/S1600536807025792 |title=Quinoxaline–dihydroxyacetic acid (1/1) |year=2007 |last1=Czapik |first1=Agnieszka |last2=Gdaniec |first2=Maria |journal=Acta Crystallographica Section E: Structure Reports Online |volume=63 |issue=7 |pages=o3081 }}</ref>
	Glyoxylic acid is usually described with the ] OCHCO<sub>2</sub>H, i.e. containing an ] ] (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 ] 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>
	:2 (HO)<sub>2</sub>CHCO<sub>2</sub>H <math>\overrightarrow{\leftarrow}</math> O<sub>2</sub> + H<sub>2</sub>O
			:]
	==Preparation==
	The compound is formed by ] of ] with hot ], the main side product being oxalic acid. ] of ] is also effective.<ref name=Ull/>
			In aqueous solution, this monohydrate exists in equilibrium with a hemi] dimer form:<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>
	The ] 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 ], which enables ]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 ]s into ]s. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.
			:]
	==Reactions and uses==
	Glyoxylic acid is about 10x stronger acid than acetic acid, with an ] of 4.7&nbsp;&times;&nbsp;10<sup>&minus;4</sup>:
	:(HO)<sub>2</sub>CHCOOH <math>\overrightarrow{\leftarrow}</math> (HO)<sub>2</sub>CHCO<sub>2</sub><sup>&minus;</sup> + H<sup>+</sup>
	With base, glyoxylic acid ]:
	:2 OCHCOOH + H<sub>2</sub>O → HOCH<sub>2</sub>COOH + HOOC&ndash;COOH
			In isolation, the aldehyde structure has as a major ] a cyclic ]ed structure with the aldehyde carbonyl in close proximity to the ] hydrogen:<ref>{{cite journal |journal= Journal of Molecular Spectroscopy |volume= 104 |issue= 1 |year= 1984 |pages= 25–39 |title= Vibrational spectra of glyoxylic acid monomers |first1= Richard L. |last1= Redington |first2= Chin-Kang Jim |last2= Liang |doi= 10.1016/0022-2852(84)90242-X |bibcode= 1984JMoSp.104...25R }}</ref>
	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 ] with ] and ].
			:]
			The ] constant of glyoxylic acid is K<sub>H</sub> = 1.09 × 10<sup>4</sup> × exp.<ref>{{cite journal|last=Ip|first=H. S. Simon|author2=Huang, X. H. Hilda |author3=Yu, Jian Zhen |title=Effective Henry's law constants of glyoxal, glyoxylic acid, and glycolic acid|journal=Geophysical Research Letters|volume=36|issue=1|pages=L01802|doi=10.1029/2008GL036212|bibcode=2009GeoRL..36.1802I|year=2009|s2cid=129747490 |url=http://repository.ust.hk/ir/bitstream/1783.1-6115/1/HLCpaper2ndrevision.pdf}}</ref>
			==Preparations==
			{{Anchor|Glyoxylate}}
			The ] of glyoxylic acid is known as '''glyoxylate''' and is the form that the compound exists in solution at neutral pH. Glyoxylate is the byproduct of the ] process in biosynthesis of several amidated ]s.
			For the historical record, glyoxylic acid was prepared from oxalic acid ]:<ref>{{cite journal|author1=Tafel, Julius |author2=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=https://zenodo.org/record/1426114}}</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> in organic synthesis, ] cathodes were applied for preparing glyoxylic acid from ] in a sulfuric acid electrolyte.<ref>{{cite book|url=https://books.google.com/books?id=ArsfQZig_9AC&pg=PA573|page=574|title=Materials Handbook: A Concise Desktop Reference|author=François Cardarelli|publisher=Springer|year=2008|isbn=978-1-84628-668-1}}</ref>
			:]
			Hot ] can ] ] to glyoxylic; however this reaction is highly exothermic and prone to thermal runaway. In addition, oxalic acid is the main side product.
			Also, ] of ] is effective.<ref name=Ull/>
			== Biological role ==
			Glyoxylate is an intermediate of the ], which enables ]s, such as bacteria,<ref name="Holms">{{cite journal|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|author=Holms WH}}</ref> fungi, and plants <ref name="Escher and Widmer F">{{cite journal|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|issue=8|pages=803–813|pmid=9377475|vauthors=Escher CL, Widmer F}}</ref> to convert ]s into ]s. The glyoxylate cycle is also important for induction of plant defense mechanisms in response to fungi.<ref>{{Cite journal| doi = 10.1016/j.fgb.2013.06.008| pmid = 23850601| issn = 1087-1845| volume = 58–59| pages = 33–41| last1 = Dubey| first1 = Mukesh K.| last2 = Broberg| first2 = Anders| last3 = Sooriyaarachchi| first3 = Sanjeewani| last4 = Ubhayasekera| first4 = Wimal| last5 = Jensen| first5 = Dan Funck| last6 = Karlsson| first6 = Magnus| title = The glyoxylate cycle is involved in pleotropic phenotypes, antagonism and induction of plant defence responses in the fungal biocontrol agent Trichoderma atroviride| journal = Fungal Genetics and Biology|date=September 2013}}</ref> The glyoxylate cycle is initiated through the activity of isocitrate lyase, which converts isocitrate into glyoxylate and succinate. Research is being done to co-opt the pathway for a variety of uses such as the biosynthesis of succinate.<ref>{{Cite journal| doi = 10.1016/j.ymben.2013.07.004| pmid = 23876414| issn = 1096-7176| volume = 20| pages = 9–19| last1 = Zhu| first1 = Li-Wen| last2 = Li| first2 = Xiao-Hong| last3 = Zhang| first3 = Lei| last4 = Li| first4 = Hong-Mei| last5 = Liu| first5 = Jian-Hua| last6 = Yuan| first6 = Zhan-Peng| last7 = Chen| first7 = Tao| last8 = Tang| first8 = Ya-Jie| title = Activation of glyoxylate pathway without the activation of its related gene in succinate-producing engineered Escherichia coli| journal = Metabolic Engineering|date=November 2013}}</ref>
			=== In humans ===
			Glyoxylate is produced via two pathways: through the oxidation of glycolate in peroxisomes or through the catabolism of hydroxyproline in mitochondria.<ref name=":0">{{Cite journal| doi = 10.1007/s00109-012-0930-z| pmid = 22729392| issn = 0946-2716| volume = 90| issue = 12| pages = 1497–1504| last1 = Belostotsky| first1 = Ruth| last2 = Pitt| first2 = James Jonathon| last3 = Frishberg| first3 = Yaacov| title = Primary hyperoxaluria type III—a model for studying perturbations in glyoxylate metabolism| journal = Journal of Molecular Medicine| date = 2012-12-01| hdl = 11343/220107| s2cid = 11549218| hdl-access = free}}</ref> In the peroxisomes, glyoxylate is converted into glycine by AGT1 or into oxalate by glycolate oxidase. In the mitochondria, glyoxylate is converted into glycine by AGT2 or into glycolate by glyoxylate reductase. A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase.<ref name=":1">{{Cite journal| doi = 10.1016/j.jhep.2010.07.036| pmid = 21093948| issn = 0168-8278| volume = 54| issue = 3| pages = 513–520| last1 = Schnedler| first1 = Nina| last2 = Burckhardt| first2 = Gerhard| last3 = Burckhardt| first3 = Birgitta C.| title = Glyoxylate is a substrate of the sulfate-oxalate exchanger, sat-1, and increases its expression in HepG2 cells| journal = Journal of Hepatology|date=March 2011}}</ref>
			[[File:Glyoxylate_metabolism_in_hepatocytes.jpg|center|thumb|600x600px|Oxalate and glyoxylate metabolism in hepatocytes.
			AGT1 and 2, alanine:glyoxylate aminotransferase 1 and 2; GO, glycolate oxidase; GR, glyoxylate reductase; HKGA, 4-hydroxy-2-ketoglutarate lyase; LDH, lactate dehydrogenase
			]]
			=== In plants ===
			In addition to being an intermediate in the ], glyoxylate is also an important intermediate in the ] pathway. Photorespiration is a result of the side reaction of RuBisCO with O<sub>2</sub> instead of CO<sub>2</sub>. While at first considered a waste of energy and resources, photorespiration has been shown to be an important method of regenerating carbon and CO<sub>2</sub>, removing toxic phosphoglycolate, and initiating defense mechanisms.<ref>{{Cite web| title = photorespiration| access-date = 2017-03-09| url = http://www2.mcdaniel.edu/Biology/botf99/photodark/photorespiration.htm| archive-date = 2006-12-11| archive-url = https://web.archive.org/web/20061211100043/http://www2.mcdaniel.edu/Biology/botf99/photodark/photorespiration.htm| url-status = dead}}</ref><ref name=":2">{{Cite journal| doi = 10.1199/tab.0130| issn = 1543-8120| volume = 8| last1 = Peterhansel| first1 = Christoph| last2 = Horst| first2 = Ina| last3 = Niessen| first3 = Markus| last4 = Blume| first4 = Christian| last5 = Kebeish| first5 = Rashad| last6 = Kürkcüoglu| first6 = Sophia| last7 = Kreuzaler| first7 = Fritz| title = Photorespiration| journal = The Arabidopsis Book| date = 2010-03-23| pmid = 22303256| pmc = 3244903| page=e0130}}</ref> In photorespiration, glyoxylate is converted from glycolate through the activity of glycolate oxidase in the peroxisome. It is then converted into glycine through parallel actions by SGAT and GGAT, which is then transported into the mitochondria.<ref>{{Cite journal| doi = 10.1016/j.jphotobiol.2014.11.009| pmid = 25528301| issn = 1011-1344| volume = 142| pages = 110–117| last1 = Zhang| first1 = Zhisheng| last2 = Mao| first2 = Xingxue| last3 = Ou| first3 = Juanying| last4 = Ye| first4 = Nenghui| last5 = Zhang| first5 = Jianhua| last6 = Peng| first6 = Xinxiang| title = Distinct photorespiratory reactions are preferentially catalyzed by glutamate:glyoxylate and serine:glyoxylate aminotransferases in rice| journal = Journal of Photochemistry and Photobiology B: Biology|date=January 2015}}</ref><ref name=":2" /> It has also been reported that the pyruvate dehydrogenase complex may play a role in glycolate and glyoxylate metabolism.<ref>{{Cite journal| doi = 10.1016/j.phytochem.2013.07.009| pmid = 23916564| issn = 0031-9422| volume = 95| pages = 168–176| last1 = Blume| first1 = Christian| last2 = Behrens| first2 = Christof| last3 = Eubel| first3 = Holger| last4 = Braun| first4 = Hans-Peter| last5 = Peterhansel| first5 = Christoph| title = A possible role for the chloroplast pyruvate dehydrogenase complex in plant glycolate and glyoxylate metabolism| journal = Phytochemistry|date=November 2013| bibcode = 2013PChem..95..168B}}</ref>
			[[File:Photorespiration_in_arabidopsis.jpg|center|thumb|600x600px|Basic overview of photorespiration in Arabidopsis.
			GGAT, glyoxylate:glutamate aminotransferase; GLYK, glycerate kinase; GO, glycolate oxidase; HPR, hydroxypyruvate reductase; PGLP, phosphoglycolate phosphatase; Rubisco, RuBP carboxylase/oxygenase; SGAT, serine:glyoxylate aminotransferase; SHM, serine hydroxymethyltransferase
			]]
			== Disease relevance ==
			{{primary sources|date=March 2017}}
			=== Diabetes ===
			Glyoxylate is thought to be a potential early marker for ].<ref name=":3" /> One of the key conditions of diabetes pathology is the production of ]s (AGEs) caused by the ].<ref>{{Cite journal| doi = 10.3389/fendo.2012.00170| issn = 1664-2392| volume = 3| pages = 170| last1 = Nguyen| first1 = Dung V.| last2 = Shaw| first2 = Lynn C.| last3 = Grant| first3 = Maria B.| title = Inflammation in the pathogenesis of microvascular complications in diabetes| journal = Frontiers in Endocrinology| date = 2012-12-21| pmid = 23267348| pmc = 3527746| doi-access = free}}</ref> AGEs can lead to further complications of diabetes, such as tissue damage and cardiovascular disease.<ref>{{Cite journal| doi = 10.1007/s00592-012-0412-3| issn = 0940-5429| volume = 50| issue = 2| pages = 101–110| last1 = Piarulli| first1 = Francesco| last2 = Sartore| first2 = Giovanni| last3 = Lapolla| first3 = Annunziata| title = Glyco-oxidation and cardiovascular complications in type 2 diabetes: a clinical update| journal = Acta Diabetologica|date=April 2013| pmid = 22763581| pmc = 3634985}}</ref> They are generally formed from reactive aldehydes, such as those present on reducing sugars and ]s. In a study, glyoxylate levels were found to be significantly increased in patients who were later diagnosed with Type II diabetes.<ref name=":3">{{Cite journal| doi = 10.1155/2014/685204| issn = 2314-6745| volume = 2014| last1 = Nikiforova| first1 = Victoria J.| last2 = Giesbertz| first2 = Pieter| last3 = Wiemer| first3 = Jan| last4 = Bethan| first4 = Bianca| last5 = Looser| first5 = Ralf| last6 = Liebenberg| first6 = Volker| last7 = Ruiz Noppinger| first7 = Patricia| last8 = Daniel| first8 = Hannelore| last9 = Rein| first9 = Dietrich| title = Glyoxylate, a New Marker Metabolite of Type 2 Diabetes| journal = Journal of Diabetes Research| date = 2014| pmid = 25525609| pmc = 4265698| pages=685204| doi-access = free}}</ref> The elevated levels were found sometimes up to three years before the diagnosis, demonstrating the potential role for glyoxylate to be an early predictive marker.
			=== Nephrolithiasis ===
			Glyoxylate is involved in the development of ], a key cause of ] (commonly known as ]). Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (sat-1), a ] responsible for ] transportation, allowing it to increase sat-1 ] expression and as a result oxalate efflux from the cell. The increased oxalate release allows the buildup of ] in the ], and thus the eventual formation of kidney stones.<ref name=":1" />
			The disruption of glyoxylate ] provides an additional mechanism of hyperoxaluria development. Loss of function mutations in the ] gene leads to a loss of the ], an ] in the ] to glyoxylate pathway. The glyoxylate resulting from this pathway is normally stored away to prevent ] to oxalate in the ]. The disrupted pathway, however, causes a buildup of ] which can also be transported to the cytosol and converted into glyoxylate through a different ]. These glyoxylate molecules can be oxidized into oxalate increasing its concentration and causing hyperoxaluria.<ref name=":0" />
			== Reactions and uses ==
			Glyoxylic acid is about ten times stronger an acid than ], with an ] of 4.7&nbsp;×&nbsp;10<sup>−4</sup> (p''K''<sub>a</sub> = 3.32):
			:OCHCO<sub>2</sub>H {{eqm}} {{chem|OCHCO|2|−}} + H<sup>+</sup>
			Heated glyoxylic acid ] in a ], forming ] and ]:<ref name=Ull/>
			:2 OCHCO<sub>2</sub>H + H<sub>2</sub>O → HOCH<sub>2</sub>CO<sub>2</sub>H + HO<sub>2</sub>CCO<sub>2</sub>H
			Glyoxylic acid gives heterocycles upon ] with ] and ].<ref name=Ull/>
			Gloxylate ]s polymerize in base, forming a poly-methyleneoxy ] with pendant ester groups.<ref name=Ull/>
	===Phenol derivatives===		===Phenol derivatives===
			In general, glyoxylic acid undergoes an ] reaction with ], a versatile step in the synthesis of several other compounds.
	Its condensation with phenols is versatile. The immediate product is 4-hydroxy]. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug ]. Reduction of the 4-hydroxymandelic acid gives 4-hydroxy], a precursor to the drug ]. Condensations with ] in place of phenol provides a route to ], a net formylation.<ref name=Ull/>
			The immediate product with ] itself is ]. This species reacts with ammonia to give hydroxyphenylglycine, a precursor to the drug ]. Reduction of the 4-hydroxymandelic acid gives ], a precursor to the drug ].
			The sequence of reactions, in which glyoxylic acid reacts with ] the phenolic component followed by oxidation and ], provides a route to ] as a net ] process.<ref name=Ull/><ref>{{cite journal|author1=Fatiadi, Alexander |author2=Schaffer, Robert|title=An Improved Procedure for Synthesis of <small>DL</small>-4-Hydroxy-3-methoxymandelic Acid (<small>DL</small>-"Vanillyl"-mandelic Acid, VMA)|journal=Journal of Research of the National Bureau of Standards Section A|year=1974|volume=78A|issue=3|pages=411–412|doi=10.6028/jres.078A.024|pmid=32189791|pmc=6742820 |doi-access=free}}</ref><ref>{{cite book|author1=Kamlet, Jonas |author2=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|author1-link=Jonas Kamlet}}</ref>
			===Hopkins Cole reaction===
			Glyoxylic acid is a component of the ], used to check for the presence of ] in proteins.<ref>{{cite book|author=R.A. Joshi|title=Question Bank of Biochemistry|url=https://books.google.com/books?id=Acf9BkEqJWYC&pg=PA64|year=2006|publisher=New Age International|isbn=978-81-224-1736-4|page=64}}</ref>
			===Hair-strengthening cosmetics===
			Glyoxylic acid enters the composition of cosmetic creams used for “Brazilian” hair-straightening treatment. Glyoxylic acid is used in cosmetic products in replacement of ] to avoid ] by this latter. Since the wider use of these products several persons developed acute ] induced by the ] of ] in their ]s.<ref name="HairStraightening2022" /> Toxicity studies on mice have further demonstrated that the transcutaneous absorption of glyoxylic acid after topical application causes the ] of ] in the ] at a much higher level than ].<ref name="Robert2024" />
			===Environmental chemistry===
			Glyoxylic acid is one of several ketone- and aldehyde-containing carboxylic acids that together are abundant in ]s. In the presence of water and sunlight, glyoxylic acid can undergo ] oxidation. Several different reaction pathways can ensue, leading to various other carboxylic acid and aldehyde products.<ref>{{cite journal | title= Aqueous Photochemistry of Glyoxylic Acid |first1= Alexis J. |last1= Eugene |first2= Sha-Sha |last2= Xia |first3= Marcelo I. |last3= Guzman |journal= J. Phys. Chem. A |year= 2016 |volume= 120 |issue= 21 |pages= 3817–3826 |doi= 10.1021/acs.jpca.6b00225 |pmid= 27192089 |bibcode= 2016JPCA..120.3817E |doi-access= free }}</ref>
	==Safety==		==Safety==
			For a long time, the compound was not considered to be highly ] in ]s ({{LD50}} of 2500&nbsp;mg/kg for ]s). However, recent observations of acute ] following exposure to ] products indicate that it is toxic.<ref name="HairStraightening2022">{{cite journal | last1=Abu-Amer | first1=Nabil | last2=Silberstein | first2=Natalie | last3=Kunin | first3=Margarita | last4=Mini | first4=Sharon | last5=Beckerman | first5=Pazit | date=2022-07-11 | title=Acute kidney injury following exposure to formaldehyde-free hair-straightening products | journal=Case Reports in Nephrology and Dialysis | publisher=S. Karger AG | volume=12 | issue=2 | issn=2296-9705 | doi=10.1159/000525567 | doi-access=free | pages=112–116| pmc=9386411 }}</ref> After ] ], glyoxylic acid contained in hair-strengthening creams causes ] ]. In contrast to ], glyoxylic acid can dramatically increase urine ] ].<ref name="Robert2024">{{Cite journal |last1=Robert |first1=Thomas |last2=Tang |first2=Ellie |last3=Kervadec |first3=Jennifer |last4=Desmons |first4=Aurore |last5=Hautem |first5=Jean-Yves |last6=Zaworski |first6=Jeremy |last7=Daudon |first7=Michel |last8=Letavernier |first8=Emmanuel |year=2024-08-26 |title=Hair-straightening cosmetics containing glyoxylic acid induce crystalline nephropathy |url=https://linkinghub.elsevier.com/retrieve/pii/S0085253824006197 |journal=Kidney International |doi=10.1016/j.kint.2024.07.032 |issn=0085-2538}}</ref>
	The compound is not very toxic with an {{LD50}} for rats of 2500 mg/kg.
			== See also ==
			* ]
	==References==		==References==
	<references/>		<references/>
			{{Authority control}}
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