Editing Pyruvic acid (section)

{{short description|Simplest of the alpha-keto acids}}
{{chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 464364811
| Name           = Pyruvic acid
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1    = Brenztraubensäure.svg
| ImageClassL1   = skin-invert-image
| ImageFileR1    = Pyruvic-acid-3D-balls.png
| PIN            = 2-Oxopropanoic acid<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 748 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| SystematicName = 2-Oxopropionic acid
| OtherNames     = Pyruvic acid<ref name=iupac2013 /><br />α-Ketopropionic acid<br />Acetylformic acid<br />Pyroracemic acid<br/>Acetylcarboxylic acid
| Section1       = {{Chembox Identifiers
| IUPHAR_ligand = 4809
| PubChem = 1060
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8558G7RUTR
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1162144
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LCTONWCANYUPML-UHFFFAOYSA-N
| Abbreviations = Pyr
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 127-17-3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1031
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00119
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 32816
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C00022
| SMILES = O=C(C(=O)O)C
}}
| Section2       = {{Chembox Properties
| Formula = C<sub>3</sub>H<sub>4</sub>O<sub>3</sub>
| MolarMass = 88.06{{nbsp}}g/mol
| Density = 1.250{{nbsp}}g/cm<sup>3</sup>
| MeltingPtC = 11.8
| BoilingPtC = 165
| pKa = 2.50<ref>{{cite book|last=Dawson|first=R. M. C.|display-authors=etal|title=Data for Biochemical Research|location= Oxford|publisher= Clarendon Press|date= 1959}}</ref>
}}
| Section4       = {{Chembox Related
| OtherAnions = [[Pyruvate]]<br /> [[File:Pyruvate_skeletal.svg|99px]]<br />[[File:Pyruvate-3D-balls.png|100px]]
| OtherFunction_label = [[keto-acid]]s, [[carboxylic acid]]s
| OtherFunction = {{ubl
 | [[Acetic acid]]
 | [[Glyoxylic acid]]
 | [[Oxalic acid]]
 | [[Propionic acid]]
 | [[Acetoacetic acid]]
}}
| OtherCompounds = {{ubl
 | [[Propionaldehyde]]
 | [[Glyceraldehyde]]
 | [[Methylglyoxal]]
 | [[Sodium pyruvate]]
}}
}}
}}

'''Pyruvic acid''' (CH<sub>3</sub>COCOOH) is the simplest of the [[keto acids|alpha-keto acids]], with a [[carboxylic acid]] and a [[ketone]] functional group. '''Pyruvate''', the [[conjugate acid|conjugate base]], CH<sub>3</sub>COCOO<sup>−</sup>, is an [[metabolic intermediate|intermediate]] in several [[metabolic pathway]]s throughout the cell.

Pyruvic acid can be made from [[glucose]] through [[glycolysis]], converted back to [[carbohydrate]]s (such as glucose) via [[gluconeogenesis]], or converted to [[fatty acid]]s through a reaction with [[acetyl-CoA]].<ref>{{cite book|first=Stuart Ira|last= Fox|title= Human Physiology|edition=12th|publisher=McGraw=Hill|date=2011|page=146}}{{ISBN missing}}</ref> It can also be used to construct the amino acid [[alanine]] and can be converted into [[ethanol]] or [[lactic acid]] via [[fermentation]].

Pyruvic acid supplies energy to [[cell (biology)|cells]] through the [[citric acid cycle]] (also known as the Krebs cycle) when oxygen is present ([[aerobic respiration]]), and alternatively [[lactic acid fermentation|ferments]] to produce [[lactic acid|lactate]] when oxygen is lacking.<ref>{{cite web|last1=Ophardt|first1=Charles E.|title=Pyruvic Acid - Cross Roads Compound|url=http://chemistry.elmhurst.edu/vchembook/603pyruvic.html|website=Virtual Chembook|publisher=Elmhurst College|access-date=April 7, 2017|archive-date=July 31, 2018|archive-url=https://web.archive.org/web/20180731021548/http://chemistry.elmhurst.edu/vchembook/603pyruvic.html}}</ref>