AFCDB: Pyruvic acid (FDB008293)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:01 UTC

Update date

2019-11-26 03:02:23 UTC

Primary ID

FDB008293

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pyruvic acid

Description

Pyruvic 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 Number

127-17-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	139 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	0.066	ChemAxon
logS	0.2	ALOGPS
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	17.99 m³·mol⁻¹	ChemAxon
Polarizability	7.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H8O6

IUPAC name

2-hydroxyprop-2-enoic acid; 2-oxopropanoic acid

InChI Identifier

InChI=1S/2C3H4O3/c2*1-2(4)3(5)6/h1H3,(H,5,6);4H,1H2,(H,5,6)

InChI Key

UNMYEGNJYFQDES-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)C(O)=O.OC(=C)C(O)=O

Average Molecular Weight

176.1241

Monoisotopic Molecular Weight

176.032087988

Classification

Description

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Alpha-keto acids and derivatives

Direct Parent

Alpha-keto acids and derivatives

Alternative Parents

Substituents

Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 40.92%; H 4.58%; O 54.50%	DFC
Melting Point	Mp ca. 13.6°	DFC
Boiling Point	Bp10 65°	DFC
Experimental Water Solubility	1000 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	pKa1 2.39 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d15 1.27	DFC
Refractive Index	n20D 1.4138	DFC

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15361

Phenol-Explorer ID

Not Available

DrugBank ID

DB00119

HMDB ID

HMDB00243

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1034261

SuperScent ID

Not Available

Wikipedia ID

Pyruvic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Alanine--glyoxylate aminotransferase 2, mitochondrial	AGXT2	Q9BYV1
Kynurenine--oxoglutarate transaminase 3	CCBL2	Q6YP21
Histidine decarboxylase	HDC	P19113
4-aminobutyrate aminotransferase, mitochondrial	ABAT	P80404
Alanine aminotransferase 1	GPT	P24298
Alanine aminotransferase 2	GPT2	Q8TD30
Selenocysteine lyase	SCLY	Q96I15
3-mercaptopyruvate sulfurtransferase	MPST	P25325
N-acetylneuraminate lyase	NPL	Q9BXD5
Cystathionine gamma-lyase	CTH	P32929
Pyruvate dehydrogenase E1 component subunit beta, mitochondrial	PDHB	P11177
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	PDHA1	P08559
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial	PDHA2	P29803
L-serine dehydratase/L-threonine deaminase	SDS	P20132
Serine dehydratase-like	SDSL	Q96GA7
Kynurenine--oxoglutarate transaminase 1	CCBL1	Q16773
Serine racemase	SRR	Q9GZT4
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial	DLAT	P10515
Monocarboxylate transporter 3	SLC16A8	O95907
Monocarboxylate transporter 7	SLC16A6	O15403
Monocarboxylate transporter 6	SLC16A5	O15375
Monocarboxylate transporter 5	SLC16A4	O15374
Phosphatidylserine decarboxylase proenzyme	PISD	Q9UG56
Malic enzyme	ME3	Q8TBJ0

Pathways

Name	SMPDB Link	KEGG Link
Alanine Metabolism	SMP00055	map00250
Amino Sugar Metabolism	SMP00045	map00520
Ammonia Recycling	SMP00009	map00910
Citric Acid Cycle	SMP00057	map00020
Cysteine Metabolism	SMP00013	map00270
Gluconeogenesis	SMP00128	map00010
Glucose-Alanine Cycle	SMP00127	Not Available
Glycine and Serine Metabolism	SMP00004	map00260
Glycolysis	SMP00040	map00010
Pyruvaldehyde Degradation	SMP00459	Not Available
Pyruvate Metabolism	SMP00060	map00620
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available
Urea Cycle	SMP00059	map00330

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sharp	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sour	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acetic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramellic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.

Pyruvic acid (FDB008293)

Structure for FDB008293 (Pyruvic acid)