1.0 2010-04-08 22:08:01 UTC 2019-11-26 03:02:23 UTC FDB008293 Pyruvic acid 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. &alpha;-ketopropionic acid 2-Ketopropionate 2-ketopropionic acid 2-oxo-propionic acid 2-Oxopropanoate 2-Oxopropanoic acid 2-Oxopropanoic acid, 9CI 2-Oxopropansaeure 2-Oxopropionate 2-Oxopropionic acid 2-Oxopropionsaeure A-ketopropionate A-ketopropionic acid a-Oxopropionsaeure Acetylformate Acetylformic acid Acide pyruvique Alpha-keto propionic acid Alpha-ketopropionate Alpha-ketopropionic acid alpha-Oxopropionsaeure Brenztraubensaeure BTS CH3COCOOH FEMA 2970 Propanoic acid, 2-oxo- Propanoic acid, 2-oxo- (9CI) Pyroracemate Pyroracemic acid Pyruvate Pyruvic acid (8CI) Sodium 2-oxopropanoate Sodium alpha-ketopropionate α-ketopropionate α-ketopropionic acid α-oxopropionsaeure C6H8O6 176.1241 176.032087988 2-hydroxyprop-2-enoic acid; 2-oxopropanoic acid 2-hydroxyprop-2-enoic acid; pyruvic acid 127-17-3 CC(=O)C(O)=O.OC(=C)C(O)=O InChI=1S/2C3H4O3/c2*1-2(4)3(5)6/h1H3,(H,5,6);4H,1H2,(H,5,6) UNMYEGNJYFQDES-UHFFFAOYSA-N 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. Alpha-keto acids and derivatives Organic compounds Organic acids and derivatives Keto acids and derivatives Alpha-keto acids and derivatives Alpha-hydroxy ketones Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic acyclic compound Alpha-hydroxy ketone Alpha-keto acid Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Ketone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Liquid logp -0.09 ALOGPS logs 0.20 ALOGPS solubility 1.39e+02 g/l ALOGPS melting_point Mp ca. 13.6° logp 0.066 ChemAxon pka_strongest_acidic 2.93 ChemAxon pka_strongest_basic -9.6 ChemAxon iupac 2-hydroxyprop-2-enoic acid; 2-oxopropanoic acid ChemAxon average_mass 176.1241 ChemAxon mono_mass 176.032087988 ChemAxon smiles CC(=O)C(O)=O.OC(=C)C(O)=O ChemAxon formula C6H8O6 ChemAxon inchi InChI=1S/2C3H4O3/c2*1-2(4)3(5)6/h1H3,(H,5,6);4H,1H2,(H,5,6) ChemAxon inchikey UNMYEGNJYFQDES-UHFFFAOYSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 17.99 ChemAxon polarizability 7.32 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon 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 Glycine and Serine Metabolism SMP00004 map00260 Glycolysis SMP00040 map00010 Pyruvaldehyde Degradation SMP00459 Pyruvate Metabolism SMP00060 map00620 Transfer of Acetyl Groups into Mitochondria SMP00466 Urea Cycle SMP00059 map00330 HMDB00243 15361 PYR #<Reference:0x000055ce3272fca8> #<Reference:0x000055ce3272faf0> #<Reference:0x000055ce3272f8c0> #<Reference:0x000055ce3272f578> #<Reference:0x000055ce3272f398> #<Reference:0x000055ce3272f0f0> #<Reference:0x000055ce3272eee8> #<Reference:0x000055ce3272ed30> #<Reference:0x000055ce3272ea60> #<Reference:0x000055ce3272e830> #<Reference:0x000055ce3272e5b0> #<Reference:0x000055ce3272e308> #<Reference:0x000055ce3272df20> #<Reference:0x000055ce3272db60> #<Reference:0x000055ce3272d818> Allium Type 1 specific Allium 4678 Apple Type 1 specific Malus pumila 283210 Asparagus Type 1 specific Asparagus officinalis 4686 Beer Type 2 specific 156.0 156.0 156.0 mg/100 g Celery stalks Type 1 specific Apium graveolens var. dulce 117781 Chickpea Type 1 specific Cicer arietinum 3827 Common pea Type 1 specific Pisum sativum 3888 Corn Type 1 specific Zea mays 4577 Cow milk, pasteurized, vitamin A + D added, 0% fat Type 2 specific Cow milk, pasteurized, vitamin A + D added, 1% fat Type 2 specific Cow milk, pasteurized, vitamin A + D added, 2% fat Type 2 specific Cow milk, pasteurized, vitamin D added, 3.25% fat Type 2 specific French plantain Type 1 specific Musa X paradisiaca 89151 Garden onion Type 1 specific Allium cepa 4679 103.4 103.4 103.4 mg/100 g Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 Ginkgo nuts Type 1 specific Ginkgo biloba 3311 Grape wine Type 2 specific 35.0 35.0 35.0 mg/100 g Herbs and Spices Unknown generic Milk (Cow) Type 2 specific 35.69 95.0 17.0 uM Peanut Type 1 specific Arachis hypogaea 3818 Port wine Type 2 specific 0.0 0.0 0.0 mg/100 g Pulses Unknown generic Wild celery Type 1 specific Apium graveolens 4045 acetic caramellic sharp sour 3-mercaptopyruvate sulfurtransferase P25325 MPST 4-aminobutyrate aminotransferase, mitochondrial P80404 ABAT Alanine aminotransferase 1 P24298 GPT Alanine aminotransferase 2 Q8TD30 GPT2 Alanine--glyoxylate aminotransferase 2, mitochondrial Q9BYV1 AGXT2 Cystathionine gamma-lyase P32929 CTH Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial P10515 DLAT Histidine decarboxylase P19113 HDC Kynurenine--oxoglutarate transaminase 1 Q16773 CCBL1 Kynurenine--oxoglutarate transaminase 3 Q6YP21 CCBL2 L-serine dehydratase/L-threonine deaminase P20132 SDS Malic enzyme Q8TBJ0 ME3 Monocarboxylate transporter 3 O95907 SLC16A8 Monocarboxylate transporter 5 O15374 SLC16A4 Monocarboxylate transporter 6 O15375 SLC16A5 Monocarboxylate transporter 7 O15403 SLC16A6 N-acetylneuraminate lyase Q9BXD5 NPL Phosphatidylserine decarboxylase proenzyme Q9UG56 PISD Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 PDHA1 Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial P29803 PDHA2 Pyruvate dehydrogenase E1 component subunit beta, mitochondrial P11177 PDHB Selenocysteine lyase Q96I15 SCLY Serine dehydratase-like Q96GA7 SDSL Serine racemase Q9GZT4 SRR Name 936 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.