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

Pyruvic acid (

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

In 1834, Théophile-Jules Pelouze distilled tartaric acid and isolated glutaric acid and another unknown organic acid. Jöns Jacob Berzelius characterized this other acid the following year and named pyruvic acid because it was distilled using heat.^[5][6] The correct molecular structure was deduced by the 1870s.^[7]

Pyruvic acid is a colorless liquid with a smell similar to that of

]

CH₃COCl + KCN → CH₃COCN + KCl

CH₃COCN → CH₃COCOOH

Biochemistry

This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. Find sources: "Pyruvic acid" – news · newspapers · books · scholar · JSTOR (December 2023) (Learn how and when to remove this template message)

Pyruvate is an important

Pyruvate is a key intersection in the network of metabolic pathways. Pyruvate can be converted into carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine, and to ethanol. Therefore, it unites several key metabolic processes.^{[citation needed]}

Pyruvic acid production by glycolysis

In the last step of

]

phosphoenolpyruvate	pyruvate kinase		pyruvic acid
	ADP	ATP
	ADP	ATP
	PEP carboxykinase

Compound C00074 at KEGG Pathway Database. Enzyme 2.7.1.40 at KEGG Pathway Database. Compound C00022 at KEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles.^{[§ 1]}

[[File:

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

|alt=Glycolysis and Gluconeogenesis edit]]

Glycolysis and Gluconeogenesis edit

1. ^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

Decarboxylation to acetyl CoA

Pyruvate decarboxylation by the pyruvate dehydrogenase complex produces acetyl-CoA.

pyruvate	pyruvate dehydrogenase complex		acetyl-CoA
	CoA + NAD+	CO2 + NADH + H+

Carboxylation to oxaloacetate

Carboxylation by pyruvate carboxylase produces oxaloacetate.

pyruvate	pyruvate carboxylase		oxaloacetate
	ATP + CO2	ADP + Pi

Transamination to alanine

Transamination by alanine transaminase produces alanine.

pyruvate	alanine transaminase		alanine
	glutamate	α-ketoglutarate
	glutamate	α-ketoglutarate

Reduction to lactate

Reduction by lactate dehydrogenase produces lactate.

pyruvate	lactate dehydrogenase		lactate
	NADH	NAD+
	NADH	NAD+

Environmental chemistry

Pyruvic acid is an abundant carboxylic acid in secondary organic aerosols.^[12]

Uses

Pyruvate is sold as a weight-loss supplement, though credible science has yet to back this claim. A systematic review of six trials found a statistically significant difference in body weight with pyruvate compared to placebo. However, all of the trials had methodological weaknesses and the magnitude of the effect was small. The review also identified adverse events associated with pyruvate such as diarrhea, bloating, gas, and increase in low-density lipoprotein (LDL) cholesterol. The authors concluded that there was insufficient evidence to support the use of pyruvate for weight loss.^[13]

There is also in vitro as well as in vivo evidence in hearts that pyruvate improves metabolism by NADH production stimulation and increases cardiac function.^[14][15]

See also

• Pyruvate scale
• Uvitonic acid

Notes

References

• Cody, G. D.; Boctor, N. Z.; Filley, T. R.; Hazen, R. M.; Scott, J. H.; Sharma, A.; Yoder, H. S. Jr (2000). "Primordial Carbonylated Iron-Sulfur Compounds and the Synthesis of Pyruvate". Science. 289 (5483): 1337–1340.
  S2CID 14911449
  .

External links

• Pyruvic acid mass spectrum

Wikimedia Commons has media related to Pyruvic acid.