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Pyruvic acid information


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
Acetoic acid
Acetylcarboxylic acid
Acetocarboxylic acid
Oxoacetol
Identifiers
CAS Number
  • 127-17-3 checkY
3D model (JSmol)
  • Interactive image
Abbreviations Pyr
ChEBI
  • CHEBI:32816 checkY
ChEMBL
  • ChEMBL1162144 checkY
ChemSpider
  • 1031 checkY
DrugBank
  • DB00119 checkY
ECHA InfoCard 100.004.387 Edit this at Wikidata
IUPHAR/BPS
  • 4809
KEGG
  • C00022 ☒N
PubChem CID
  • 1060
UNII
  • 8558G7RUTR checkY
CompTox Dashboard (EPA)
  • DTXSID2021650 Edit this at Wikidata
InChI
  • InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) checkY
    Key: LCTONWCANYUPML-UHFFFAOYSA-N checkY
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[2]
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).
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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]

  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 (inactive 2024-04-10). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
  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.

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Pyruvic acid

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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...

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Keto acid

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prodrug scaffold. Important representatives: pyruvic acid, pervasive intermediate in metabolism. oxaloacetic acid, a component of the Krebs cycle. alpha-ketoglutarate...

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Sodium pyruvate

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Sodium pyruvate is a salt of the conjugate anion form of pyruvic acid, known as pyruvate. It is commonly added to cell culture media as an additional source...

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Methylglyoxal

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compound with the formula CH3C(O)CHO. It is a reduced derivative of pyruvic acid. It is a reactive compound that is implicated in the biology of diabetes...

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Fatty acid

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fatty acids exuded by mammalian skin, together with lactic acid and pyruvic acid, is distinctive and enables animals with a keen sense of smell to differentiate...

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Methyl red

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produce pyruvic acid from glucose metabolism. Some enterics subsequently use the mixed acid pathway to metabolize pyruvic acid to other acids, such as...

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Indole

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synthesis by reacting phenylhydrazine with pyruvic acid followed by decarboxylation of the formed indole-2-carboxylic acid. This has also been accomplished in...

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Phenolic content in wine

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glucoside Cyanidin-3-O-glucoside-pyruvic acid Cyanidin-3-O-acetylglucoside-pyruvic acid Cyanidin-coumaroylglucoside-pyruvic acid Delphinidin Delphinidin 3O...

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Amino acid synthesis

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from pyruvic acid and alpha-ketoglutarate. Enzymes involved in this biosynthesis include acetolactate synthase (also known as acetohydroxy acid synthase)...

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Dicarbonyl

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diesters with diamines gives cyclic diamides. α-Keto-acids and -esters are well known. Pyruvic acid (CH3C(O)CO2H) is the parent α-ketoacid. Its conjugate...

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Ketone body

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in the liver where it is converted into lactic acid, which can, in turn, be oxidized into pyruvic acid, and only then into acetyl-CoA. Ketone bodies have...

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Neuraminic acid

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Neuraminic acid may also be visualized as the product of an aldol-condensation of pyruvic acid and D-mannosamine (2-amino-2-deoxy-mannose). Neuraminic acid does...

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Triose

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glyceraldehyde-3-phosphate and dihydroxyacetone phosphate. Lactic acid and pyruvic acid are later derived from these molecules. "Trioses - Three Carbon...

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Bromopyruvic acid

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Bromopyruvic acid is the organic compound with the formula BrCH2COCO2H. This colorless solid is the brominated derivative of pyruvic acid. It bears structural...

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Pyruvate decarboxylase

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decarboxylation of pyruvic acid to acetaldehyde. It is also called 2-oxo-acid carboxylase, alpha-ketoacid carboxylase, and pyruvic decarboxylase. In anaerobic...

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Phosphoenolpyruvic acid

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the action of the enzyme enolase on 2-phosphoglyceric acid. Metabolism of PEP to pyruvic acid by pyruvate kinase (PK) generates adenosine triphosphate...

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List of carboxylic acids

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Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature...

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Cellular respiration

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process converts one molecule of glucose into two molecules of pyruvate (pyruvic acid), generating energy in the form of two net molecules of ATP. Four molecules...

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Glyoxylic acid

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Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic...

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Red onion

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have a sweeter flavor than white or yellow onions due to low levels of pyruvic acid and sulfur compounds. They are often consumed raw (and can be added to...

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Pyruvate scale

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μmol/gfw (micromoles per gram fresh weight). It is named after pyruvic acid, the alpha-keto acid co-product created in the biochemical pathway that forms...

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Acetolactic acid

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α-Acetolactic acid is produced from two molecules of pyruvic acid by acetolactate synthase. α-Acetolactic acid can also be decarboxylated by alpha-acetolactate...

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Oxidative decarboxylation

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(NAD+). During the reaction, E1 participates in the decarboxylation of pyruvic acid, and then TPP connects the acetyl group after the reaction. The carbonyl...

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Carboxylic acid

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carboxylic acid is an organic acid that contains a carboxyl group (−C(=O)−OH) attached to an R-group. The general formula of a carboxylic acid is often...

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Glycolysis

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post-glycolytic pathways: Fatty acid synthesis Cholesterol synthesis The citric acid cycle which in turn leads to: Amino acid synthesis Nucleotide synthesis...

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