Pyruvic Acid

HCID 178796522

Grundinformationen

CAS
1892-67-7
Standard-SMILES
CC(=O)C(=O)O
InChIKey
LCTONWCANYUPML-UHFFFAOYSA-N
Summenformel
C3H4O3
Durchschnittliche Molmasse
88,06 g/mol

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Pyruvic Acid
IUPAC
2-oxopropanoic acid
Englischer Name
2-Oxopropanoic acid
Summenformel
C3H4O3
Molmasse
88.06206

Namen und Synonyme

Pyruvic acid2-Oxopropanoic acid127-17-3acetylformic acidPyroracemic acid2-Oxopropionic acidPropanoic acid, 2-oxo-alpha-ketopropionic acid2-Ketopropionic acid2-Oxopropansaeure2-Oxopropionsaeurealpha-Oxopropionsaeure
Weitere Namen anzeigen
2-oxo-propionic acidacide pyruviquea-Ketopropionic acidCH3COCOOHFEMA No. 2970BrenztraubensaeureDTXSID2021650NSC-179

Datenbank-Bezeichner

CAS
1892-67-7
ChEBI
CHEBI:32816
UNII
8558G7RUTR
EC Number
204-824-3
Nikkaji
J2.015J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,3
Polarare Oberfläche (TPSA)
54,4 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

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
LogP-0.9

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 4 Einträge

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Commission Regulation (EC) No 1565/2000 (Repealed by Com.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 Eintrag

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%)

Toxikologische Informationen

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 Eintrag

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).

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Einträge

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

Verwendung und Herstellung

Uses · 2 Einträge

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 Einträge

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

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