Pyruvic acid

Pyruvic acid
Names
Preferred IUPAC name
2-Oxopropanoic acid[1]
Systematic IUPAC name
2-Oxopropionic acid
Other names
Pyruvic acid[1]
α-Ketopropionic acid
Acetylformic acid
Pyroracemic acid
Acetylcarboxylic acid
Identifiers
3D model (JSmol)
Abbreviations Pyr
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.387 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) checkY
    Key: LCTONWCANYUPML-UHFFFAOYSA-N checkY
  • O=C(C(=O)O)C
Properties
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[2]
Related compounds
Other anions
 Pyruvate

Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyruvic 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]

  1. ^ 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. ISBN 978-0-85404-182-4.
  2. ^ Dawson, R. M. C.; et al. (1959). Data for Biochemical Research. Oxford: Clarendon Press.
  3. ^ Fox, Stuart Ira (2011). Human Physiology (12th ed.). McGraw=Hill. p. 146.[ISBN missing]
  4. ^ Ophardt, Charles E. "Pyruvic Acid - Cross Roads Compound". Virtual Chembook. Elmhurst College. Archived from the original on July 31, 2018. Retrieved April 7, 2017.