Record Information
Version1.0
Creation date2010-04-08 22:08:01 UTC
Update date2019-11-27 17:14:15 UTC
Primary IDFDB008293
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyruvic acid
DescriptionPyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures (From Stedman, 26th ed.). Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds); 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.; Pyruvate is an important chemical compound in biochemistry. It is the output of the anaerobic metabolism of glucose known as glycolysis. One molecule of glucose breaks down into two molecules of pyruvate, which are then used to provide further energy, in one of two ways. Pyruvate 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.; Pyruvic acid (CH3COCOOH) is an organic acid. It is also a ketone, as well as being the simplest alpha-keto acid. The carboxylate (COOH) ion (anion) of pyruvic acid, CH3COCOO-, is known as pyruvate, and is a key intersection in several metabolic pathways. It can be made from glucose through glycolysis, supplies energy to living cells in the citric acid cycle, and can also be converted to carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine and to ethanol.; 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, by the oxidation of propylene glycol by a strong oxidizer (eg. potassium permanganate or bleach), or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:; 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. Pyruvic acid is isolated from cane sugar fermentation broth, Cicer arietinum (chickpea), Pisum sativum (pea), Trigonella cerulea (sweet trefoil) and peppermint. It can be used as a flavouring ingredient.
CAS Number127-17-3
Structure
Thumb
Synonyms
SynonymSource
α-ketopropionic acidbiospider
2-KetopropionateGenerator
2-ketopropionic acidbiospider
2-oxo-propionic acidbiospider
2-Oxopropanoatebiospider
2-Oxopropanoic acidbiospider
2-Oxopropanoic acid, 9CIdb_source
2-OxopropansaeureChEBI
2-Oxopropionatebiospider
2-Oxopropionic acidbiospider
2-OxopropionsaeureChEBI
A-ketopropionatebiospider
A-ketopropionic acidbiospider
a-OxopropionsaeureGenerator
Acetylformatebiospider
Acetylformic aciddb_source
Acide pyruviqueChEBI
Alpha-keto propionic acidbiospider
Alpha-ketopropionatebiospider
Alpha-ketopropionic acidbiospider
alpha-OxopropionsaeureChEBI
BrenztraubensaeureChEBI
BTSbiospider
CH3COCOOHbiospider
FEMA 2970db_source
Propanoic acid, 2-oxo-biospider
Propanoic acid, 2-oxo- (9CI)biospider
Pyroracematebiospider
Pyroracemic aciddb_source
Pyruvatebiospider
Pyruvic acid (8CI)biospider
Sodium 2-oxopropanoatebiospider
Sodium alpha-ketopropionatebiospider
α-ketopropionateGenerator
α-ketopropionic acidGenerator
α-oxopropionsaeureGenerator
Predicted Properties
PropertyValueSource
Water Solubility139 g/LALOGPS
logP-0.09ALOGPS
logP0.066ChemAxon
logS0.2ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity17.99 m³·mol⁻¹ChemAxon
Polarizability7.32 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H8O6
IUPAC name2-hydroxyprop-2-enoic acid; 2-oxopropanoic acid
InChI IdentifierInChI=1S/2C3H4O3/c2*1-2(4)3(5)6/h1H3,(H,5,6);4H,1H2,(H,5,6)
InChI KeyUNMYEGNJYFQDES-UHFFFAOYSA-N
Isomeric SMILESCC(=O)C(O)=O.OC(=C)C(O)=O
Average Molecular Weight176.1241
Monoisotopic Molecular Weight176.032087988
Classification
DescriptionThis compound belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct ParentAlpha-keto acids and derivatives
Alternative Parents
Substituents
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 40.92%; H 4.58%; O 54.50%DFC
Melting PointMp ca. 13.6°DFC
Boiling PointBp10 65°DFC
Experimental Water Solubility1000 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKapKa1 2.39 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd15 1.27DFC
Refractive Indexn20D 1.4138DFC
Spectra
SpectraNot Available
ChemSpider ID1031
ChEMBL IDCHEMBL1162144
KEGG Compound IDC00022
Pubchem Compound ID1060
Pubchem Substance IDNot Available
ChEBI ID15361
Phenol-Explorer IDNot Available
DrugBank IDDB00119
HMDB IDHMDB00243
CRC / DFC (Dictionary of Food Compounds) IDDFR44-K:DFR44-K
EAFUS ID3271
Dr. Duke IDPYRUVIC-ACID
BIGG ID33546
KNApSAcK IDC00001200
HET IDPYR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1034261
SuperScent IDNot Available
Wikipedia IDPyruvic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
Enzymes
NameGene NameUniProt ID
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT2Q9BYV1
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Histidine decarboxylaseHDCP19113
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Alanine aminotransferase 1GPTP24298
Alanine aminotransferase 2GPT2Q8TD30
Selenocysteine lyaseSCLYQ96I15
3-mercaptopyruvate sulfurtransferaseMPSTP25325
N-acetylneuraminate lyaseNPLQ9BXD5
Cystathionine gamma-lyaseCTHP32929
Pyruvate dehydrogenase E1 component subunit beta, mitochondrialPDHBP11177
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1P08559
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrialPDHA2P29803
L-serine dehydratase/L-threonine deaminaseSDSP20132
Serine dehydratase-likeSDSLQ96GA7
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Serine racemaseSRRQ9GZT4
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialDLATP10515
Monocarboxylate transporter 3SLC16A8O95907
Monocarboxylate transporter 7SLC16A6O15403
Monocarboxylate transporter 6SLC16A5O15375
Monocarboxylate transporter 5SLC16A4O15374
Phosphatidylserine decarboxylase proenzymePISDQ9UG56
Malic enzymeME3Q8TBJ0
Pathways
NameSMPDB LinkKEGG Link
Alanine MetabolismSMP00055 map00250
Amino Sugar MetabolismSMP00045 map00520
Ammonia RecyclingSMP00009 map00910
Citric Acid CycleSMP00057 map00020
Cysteine MetabolismSMP00013 map00270
GluconeogenesisSMP00128 map00010
Glucose-Alanine CycleSMP00127 Not Available
Glycine and Serine MetabolismSMP00004 map00260
GlycolysisSMP00040 map00010
Pyruvaldehyde DegradationSMP00459 Not Available
Pyruvate MetabolismSMP00060 map00620
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sharp
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sour
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acetic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramellic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.