Pyruvic acid

Jump to: navigation, search
Template:Chembox E number
Pyruvic acid
IUPAC name 2-oxopropanoic acid
Other names α-ketopropionic acid; acetylformic acid; pyroracemic acid; Pyr
3D model (JSmol)
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
Molar mass 88.06 g/mol
Density 1.250 g/cm³
Melting point
Boiling point
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

WikiDoc Resources for Pyruvic acid


Most recent articles on Pyruvic acid

Most cited articles on Pyruvic acid

Review articles on Pyruvic acid

Articles on Pyruvic acid in N Eng J Med, Lancet, BMJ


Powerpoint slides on Pyruvic acid

Images of Pyruvic acid

Photos of Pyruvic acid

Podcasts & MP3s on Pyruvic acid

Videos on Pyruvic acid

Evidence Based Medicine

Cochrane Collaboration on Pyruvic acid

Bandolier on Pyruvic acid

TRIP on Pyruvic acid

Clinical Trials

Ongoing Trials on Pyruvic acid at Clinical

Trial results on Pyruvic acid

Clinical Trials on Pyruvic acid at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Pyruvic acid

NICE Guidance on Pyruvic acid


FDA on Pyruvic acid

CDC on Pyruvic acid


Books on Pyruvic acid


Pyruvic acid in the news

Be alerted to news on Pyruvic acid

News trends on Pyruvic acid


Blogs on Pyruvic acid


Definitions of Pyruvic acid

Patient Resources / Community

Patient resources on Pyruvic acid

Discussion groups on Pyruvic acid

Patient Handouts on Pyruvic acid

Directions to Hospitals Treating Pyruvic acid

Risk calculators and risk factors for Pyruvic acid

Healthcare Provider Resources

Symptoms of Pyruvic acid

Causes & Risk Factors for Pyruvic acid

Diagnostic studies for Pyruvic acid

Treatment of Pyruvic acid

Continuing Medical Education (CME)

CME Programs on Pyruvic acid


Pyruvic acid en Espanol

Pyruvic acid en Francais


Pyruvic acid in the Marketplace

Patents on Pyruvic acid

Experimental / Informatics

List of terms related to Pyruvic acid

Please Take Over This Page and Apply to be Editor-In-Chief for this topic: There can be one or more than one Editor-In-Chief. You may also apply to be an Associate Editor-In-Chief of one of the subtopics below. Please mail us [1] to indicate your interest in serving either as an Editor-In-Chief of the entire topic or as an Associate Editor-In-Chief for a subtopic. Please be sure to attach your CV and or biographical sketch.


Pyruvic acid (CH3COCO2H) is an alpha-keto acid. Pyruvate plays an important role in biochemical processes. The carboxylate anion of pyruvic acid is known as pyruvate.


Pyruvic acid is a colorless liquid with a smell similar to that of acetic acid. It is miscible with water, and soluble in ethanol and diethyl ether. In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and potassium hydrogen sulfate, or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:


Biochemical role

Pyruvate is an important chemical compound in biochemistry. It is the output of the aerobic metabolism of glucose known as glycolysis. One molecule of glucose breaks down into two molecules of pyruvic acid, which are then used to provide further energy, in one of two ways. Pyruvic acid is converted into acetyl-coenzyme A, which is the main input for a series of reactions known as the Krebs cycle. Pyruvate is also converted to oxaloacetate by an anaplerotic reaction which replenishes Krebs cycle intermediates; alternatively, the oxaloacetate is used for gluconeogenesis. These reactions are named after Hans Adolf Krebs, the biochemist awarded the 1953 Nobel Prize for physiology, jointly with Fritz Lipmann, for research into metabolic processes. The cycle is also called the citric acid cycle, because citric acid is one of the intermediate compounds formed during the reactions.

If insufficient oxygen is available, the acid is broken down anaerobically, creating lactic acid in animals and ethanol in plants. Pyruvate from glycolysis is converted by anaerobic respiration to lactate using the enzyme lactate dehydrogenase and the coenzyme NADH in lactate fermentation, or to acetaldehyde and then to ethanol in alcoholic fermentation.

Pyruvic acid is a key intersection in the network of metabolic pathways. Pyruvic acid can be converted to 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.

The pyruvic acid derivative bromopyruvic acid is being studied for potential cancer treatment applications, by Young Hee Ko at Johns Hopkins University and others in ways that would support the Warburg hypothesis on the cause(s) of cancer.

Pyruvate production by glycolysis

In glycolysis, phosphoenolpyruvate (PEP) is converted to pyruvate by pyruvate kinase. This reaction is strongly exergonic and irreversible; in gluconeogenesis it takes two enzymes, pyruvate carboxylase and PEP carboxykinase to catalyze the reverse transformation of pyruvate to PEP. The arrow indicating a reverse reaction in the Figure below is incorrect.

phosphoenolpyruvate {{{forward_enzyme}}} pyruvate
Phosphoenolpyruvate wpmp.png   Pyruvate wpmp.png
{{{minor_forward_substrate(s)}}} {{{minor_forward_product(s)}}}
  Pyruvate kinase

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

Pyruvate decarboxylation to acetyl CoA

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

pyruvate {{{forward_enzyme}}} acetyl-CoA
Pyruvate wpmp.png   Acetyl co-A wpmp.png
{{{minor_forward_substrate(s)}}} {{{minor_forward_product(s)}}}

Note that decarboxylation is only one of several possible reactions for pyruvate.

Role in the origin of life

Current evolutionary theory on the origin of life posits that the first organisms were anaerobic because the atmosphere of prebiotic Earth was almost devoid of oxygen. As such, requisite biochemical materials must have preceded life and recent experiments indicate that pyruvate can be synthesized abiotically. In vitro, iron sulfide at sufficient pressure and temperature catalyzes the formation of pyruvic acid. Thus, argues Günter Wächtershäuser, the mixing of iron-rich crust with hydrothermal vent fluid is suspected of providing the fertile basis for the formation of life.

External links


  • George D. Cody, Nabil Z. Boctor, Timothy R. Filley, Robert M. Hazen, James H. Scott, Anurag Sharma, Hatten S. Yoder Jr., "Primordial Carbonylated Iron-Sulfur Compounds and the Synthesis of Pyruvate," Science, 289 (5483) (25 August 2000) pp. 1337 - 1340. [2]

Cost Effectiveness of Pyruvic acid

| group5 = Clinical Trials Involving Pyruvic acid | list5 = Ongoing Trials on Pyruvic acid at Clinical Trials.govTrial results on Pyruvic acidClinical Trials on Pyruvic acid at Google

| group6 = Guidelines / Policies / Government Resources (FDA/CDC) Regarding Pyruvic acid | list6 = US National Guidelines Clearinghouse on Pyruvic acidNICE Guidance on Pyruvic acidNHS PRODIGY GuidanceFDA on Pyruvic acidCDC on Pyruvic acid

| group7 = Textbook Information on Pyruvic acid | list7 = Books and Textbook Information on Pyruvic acid

| group8 = Pharmacology Resources on Pyruvic acid | list8 = AND (Dose)}} Dosing of Pyruvic acidAND (drug interactions)}} Drug interactions with Pyruvic acidAND (side effects)}} Side effects of Pyruvic acidAND (Allergy)}} Allergic reactions to Pyruvic acidAND (overdose)}} Overdose information on Pyruvic acidAND (carcinogenicity)}} Carcinogenicity information on Pyruvic acidAND (pregnancy)}} Pyruvic acid in pregnancyAND (pharmacokinetics)}} Pharmacokinetics of Pyruvic acid

| group9 = Genetics, Pharmacogenomics, and Proteinomics of Pyruvic acid | list9 = AND (pharmacogenomics)}} Genetics of Pyruvic acidAND (pharmacogenomics)}} Pharmacogenomics of Pyruvic acidAND (proteomics)}} Proteomics of Pyruvic acid

| group10 = Newstories on Pyruvic acid | list10 = Pyruvic acid in the newsBe alerted to news on Pyruvic acidNews trends on Pyruvic acid

| group11 = Commentary on Pyruvic acid | list11 = Blogs on Pyruvic acid

| group12 = Patient Resources on Pyruvic acid | list12 = Patient resources on Pyruvic acidDiscussion groups on Pyruvic acidPatient Handouts on Pyruvic acidDirections to Hospitals Treating Pyruvic acidRisk calculators and risk factors for Pyruvic acid

| group13 = Healthcare Provider Resources on Pyruvic acid | list13 = Symptoms of Pyruvic acidCauses & Risk Factors for Pyruvic acidDiagnostic studies for Pyruvic acidTreatment of Pyruvic acid

| group14 = Continuing Medical Education (CME) Programs on Pyruvic acid | list14 = CME Programs on Pyruvic acid

| group15 = International Resources on Pyruvic acid | list15 = Pyruvic acid en EspanolPyruvic acid en Francais

| group16 = Business Resources on Pyruvic acid | list16 = Pyruvic acid in the MarketplacePatents on Pyruvic acid

| group17 = Informatics Resources on Pyruvic acid | list17 = List of terms related to Pyruvic acid


cs:Kyselina pyrohroznová da:Pyruvat de:Brenztraubensäure de:Pyruvate id:Asam piruvat it:acido piruvico lv:Pirovīnogskābe lb:Pyruvat hu:Piroszőlősav nl:Pyrodruivenzuur fi:Pyruvaatti sv:Pyrodruvsyra