Pyruvic acid

Pyruvic acid
Names
	Preferred IUPAC name 2-Oxopropanoic acid
	Systematic IUPAC name 2-Oxopropionic acid
	Other names Pyruvic acid; α-Ketopropionic acid; Acetylformic acid; Pyroracemic acid; Acetoic acid; Acetylcarboxylic acid; Acetocarboxylic acid; Oxoacetol
Identifiers
CAS Number	127-17-3 ;
3D model (JSmol)	Interactive image;
Abbreviations	Pyr
ChEBI	CHEBI:32816 ;
ChEMBL	ChEMBL1162144 ;
ChemSpider	1031 ;
DrugBank	DB00119 ;
ECHA InfoCard	100.004.387
IUPHAR/BPS	4809;
KEGG	C00022 ;
PubChem CID	1060;
UNII	8558G7RUTR ;
CompTox Dashboard (EPA)	DTXSID2021650 ;
	InChI InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) Key: LCTONWCANYUPML-UHFFFAOYSA-N ;
	SMILES O=C(C(=O)O)C;
Properties
Chemical formula	C3H4O3
Molar mass	88.06 g/mol
Density	1.250 g/cm3
Melting point	11.8 °C (53.2 °F; 284.9 K)
Boiling point	165 °C (329 °F; 438 K)
Acidity (pKa)	2.50
Related compounds
Other anions	Pyruvate; ;
Related keto-acids, carboxylic acids	Acetic acid; Glyoxylic acid; Oxalic acid; Propionic acid; Acetoacetic acid;
Related compounds	Propionaldehyde; Glyceraldehyde; Methylglyoxal; Sodium pyruvate;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Pyruvic acid (IUPAC name: 2-oxopropanoic acid, also called acetoic acid) (CH₃COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH₃COCOO⁻, is an intermediate in several metabolic pathways throughout the cell.

Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or converted to fatty acids through a reaction with acetyl-CoA.^[3] 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 cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking.^[4]

^ ^a ^b Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001 (inactive 2024-04-10). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
^ Dawson, R. M. C.; et al. (1959). Data for Biochemical Research. Oxford: Clarendon Press.
^ Fox, Stuart Ira (2011). Human Physiology (12th ed.). McGraw=Hill. p. 146.^{[ISBN missing]}
^ Ophardt, Charles E. "Pyruvic Acid - Cross Roads Compound". Virtual Chembook. Elmhurst College. Archived from the original on July 31, 2018. Retrieved April 7, 2017.