Pyruvic Acid

HCID 1060CAS 127-17-3
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(=O)C(=O)O
InChIKey
LCTONWCANYUPML-UHFFFAOYSA-N
Molecular formula
C3H4O3
Average molar mass
88.06 g/mol
Monoisotopic mass
88.01604399

Overview

Pyruvic acid is a 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis. It has a role as a cofactor and a fundamental metabolite. It is functionally related to a propionic acid. It is a conjugate acid of a pyruvate.

Names & identifiers

Preferred name
Pyruvic Acid
IUPAC
2-oxopropanoic acid
English name
Pyruvic acid
Molecular formula
C3H4O3
Molecular weight
88.06

Names & synonyms

Pyruvic acid2-Oxopropanoic acid127-17-3acetylformic acidPyroracemic acid2-Oxopropionic acidPropanoic acid, 2-oxo-alpha-ketopropionic acid2-Ketopropionic acid2-Oxopropansaeure2-Oxopropionsaeurealpha-Oxopropionsaeure
Show more names
pyruvicFEMA 29702-oxo-propanoicaciNSC 179Pyruvia AcidACID PYRUVATE
2-oxo-propionic acidacide pyruviquea-Ketopropionic acidCH3COCOOHFEMA No. 2970BrenztraubensaeureDTXSID2021650NSC-179

Database identifiers

CAS
127-17-3
PubChem CID
1060
DTXSID
DTXSID2021650
ChEBI
CHEBI:32816
UNII
8558G7RUTR
EC Number
204-824-3
Nikkaji
J2.015J

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Other Biomolecules
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106]
SpringerMaterials PropertiesCoriolis coupling
FragrancesFragrance Ingredient (Pyruvic acid) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Physicochemical properties

Melting point
11 · 11-12 °C (lit.)
Boiling point
165 °C · 165 °C (lit.)
Density
1.267 g/mL · 1.267 g/mL at 25 °C (lit.)
vapor pressure
1.72 hPa · 1.72hPa at 25℃
FEMA
2970 · 2970 | PYRUVIC ACID
refractive index
20 · n20/D 1.428(lit.)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1823 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: Propanoic acid, 2-oxo-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 13-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23815

Pyruvic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary · 1 item

Causes degenerative changes to brain in acute cerebral studies of rats; [RTECS] Polymerizes and decomposes on standing unless pure and stored in airtight container; [Merck Index] Safe when used as a flavoring agent in food; [JECFA] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesSkin Corr. 1B (100%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesPyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation.
Toxicity Summary · 1 item

Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. This inotropic effect is striking in hearts stunned by ischemia/reperfusion. The inotropic effect of pyruvate requires intracoronary infusion. Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. Pyruvate dehydrogenase is inactivated in ischemia myocardium. Yet another is reduction of cytosolic inorganic phosphate concentration. Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
UZ0829800
ridadr
UN 3265 8/PG 2
hs_code
29335995

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Pyruvic acid or pyruvate is a key intermediate in the glycolytic and pyruvate dehydrogenase pathways, which are involved in biological energy production. Pyruvate is widely found in living organisms. It is not an essential nutrient since it can be synthesized in the cells of the body. Certain fruits and vegetables are rich in pyruvate. For example, an average-size red apple contains approximately 450 milligrams. Dark beer and red wine are also rich sources of pyruvate. Recent research suggests that pyruvate in high concentrations may have a role in cardiovascular therapy, as an inotropic agent. Supplements of this dietary substance may also have bariatric and ergogenic applications.

Mechanism of Action · 1 item

Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. This inotropic effect is striking in hearts stunned by ischemia/reperfusion. The inotropic effect of pyruvate requires intracoronary infusion. Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. Pyruvate dehydrogenase is inactivated in ischemia myocardium. Yet another is reduction of cytosolic inorganic phosphate concentration. Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione.

Metabolism/Metabolites · 2 items

In the liver, pyruvate is metabolized via several pathways.

In the liver, pyruvate is metabolized via several pathways.

Absorption, Distribution and ExcretionPyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation.
Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular

Uses & manufacturing

Uses · 2 items

Intermediate in sugar metabolism and alcoholic fermentation; [Merck Index] Used as flavoring agent or adjuvant; [FDA]

For nutritional supplementation, also for treating dietary shortage or imbalance

Use Classification · 6 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationPropanoic acid, 2-oxo-: ACTIVE
Applications · 5 items

UsesIntermediate in sugar metabolism and in enzymatic carbohydrate degradation (alcoholic fermentation) where it is converted to acetaldehyde and CO2 by carboxylase. In muscle, Pyruvic acid (derived from glycogen) is reduced to lactic acid during exertion, which is reoxidized and partially retransformed to glycogen during rest. The liver can convert Pyruvic acid to alanine by amination. A diagnostic agent for Parkinson disease.

OccurrenceIsolated from cane sugar fermentation broth and from a few plants; also reported found in peppermint, raw asparagus, leaves and stalk of celery, onion, rutabaga, milk, cream, buttermilk, wheaten bread, blue cheeses, cheddar cheese, cottage cheese, provolone cheese, yogurt, beef, Virginia tobacco, beer, white wine, botrytised wine, cocoa and sake.

UsesPyruvic acid is used as a component in culture broths and media as commercial red seaweed polysaccharide. It is involved in the construction of amino acid alanine as well as supplies energy to living cells via citric acid cycle (Krebs cycle). It reacts with N-acetyl mannosamine by an aldol-type condensation to prepare sialic acid. It is employed to study the cultivation of soil bacteria as micro colonies using soil substrate membrane system. It finds application in liquid chromatography and in the determination of organic acids in red wine.

Usespyruvic acid is an alpha hydroxy acid that can be irritating and is considered difficult to work with. It has a larger molecular size than the most commonly used AHAs. Sodium pyruvate is more commonly used, and is an organic salt.

General DescriptionPyruvic acid is the key component formed during the hydrolysis of flavor-precursors called S-alk(en)yl-L-cysteine-sulfoxides in onion tissues by allinase during maceration or chopping. The amount of pyruvic acid formed is used as a measure for onion pungency.

Preparation methods · 1 item

PreparationBy distillation of tartaric acid in the presence of potassium acid sulfate as a dehydrating agent; from acetyl chloride and potassium cyanide to yield the nitrile, which is subsequently acid hydrolyzed to the acid; pyruvic acid must be rectified under vacuum.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]
Additional notes · 1 item

DefinitionPyruvic acid is an important organic chemical intermediate, an intermediate compound in the metabolism of carbohydrates, proteins, and fats, and is used in a variety of fields, including the pharmaceutical, cosmetic, food, and chemical industries. It has roles as a basic metabolite and cofactor. In thiamine deficiency, its oxidation is retarded and it tends to accumulate in neurostructural tissues causing neurological damage. In vitro studies have shown that pyruvic acid modulates cardiac function at physiological or low doses, but can cause cardiomyocyte damage at high doses.

Related reactions

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Linked notes

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