5699-58-1

Basic information

• Product Name: 2,4-dioxovaleric acid
• Synonyms: 2,4-dioxovaleric acid;acetylpyruvic acid;2,4-Dioxopentanoic acid
• CAS NO: 5699-58-1
• Molecular Formula: C₅H₆O₄
• Molecular Weight: 130.09874
• EINECS: 227-181-0
• Mol File: 5699-58-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 99.5°C
• Boiling Point: 160.75°C (rough estimate)
• Flash Point: 110.5 °C
• Appearance: /
• Density: 1.1349 (rough estimate)
• Vapor Pressure: 0.0172mmHg at 25°C
• Refractive Index: 1.4240 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 2.19±0.54(Predicted)
• CAS DataBase Reference: 2,4-dioxovaleric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dioxovaleric acid(5699-58-1)
• EPA Substance Registry System: 2,4-dioxovaleric acid(5699-58-1)

Safety Data

• Hazardous Substances Data: 5699-58-1(Hazardous Substances Data)

Usage

Uses

Acetylpyruvic acid is a derivative of pyruvic acid (P998900) which is an intermediate 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.

Definition

ChEBI: A dioxo monocarboxylic acid that is pentanoic acid carrying two oxo groups at positions 2 and 4.

InChI:InChI=1/C5H6O4/c1-3(6)2-4(7)5(8)9/h2H2,1H3,(H,8,9)/p-1

Upstream product

• 615-79-2 ethyl 2,4-diketopentanoate 
• 45014-40-2 (Z)-4-(Cyanomethyl-amino)-2-oxo-pent-3-enoic acid 
• 20577-61-1 methyl 2,4-dioxopentanoate 

Downstream Products

• 63024-81-7 4-acetyl-5-phenyl-dihydro-furan-2,3-dione 
• 696-22-0 5-methyl-2H-pyrazole-3-carboxylic acid 
• 69225-88-3 (1RS)-1,2,3,4-Tetrahydro-1-(2-oxopropyl)-β-carbolin 
• 1053168-39-0 5-methyl-1-(4-nitro-phenyl)-1H-pyrazole-3-carboxylic acid 
• 503300-35-4 acetoacetanilide 
• 10199-57-2 5-methyl-1-phenyl-1H-pyrazole-3-carboxylic acid 
• 3405-77-4 5-methylisoxazole 3-carboxylic acid 
• 625-72-9 (R)-3-hydroxybutyric acid 
• 120800-48-8 1-acetyl-5-methyl-1H-pyrazole-3-carboxylic acid 
• 1136-76-1 3-methyl-1-phenyl-1H-pyrazole-5-carboxylic acid 
• 861557-11-1 2,4-dioxo-valeric acid-(N-methyl-anilide) 
• 618101-88-5 1-(4-bromophenyl)-3-methyl-1H-pyrazole-5-carboxylic acid 
• 54031-97-9 2-Hydroxy-4-oxopentanoic acid 
• 124-38-9 carbon dioxide 

Relevant articles and documents

The hydratase activity of malonate semialdehyde decarboxylase: Mechanistic and evolutionary implications

Malonate semialdehyde decarboxylase (MSAD) is a member of the tautomerase superfamily, a group of structurally homologous proteins that have a characteristic β-α-β-fold and a catalytic amino-terminal proline. In addition to its physiological decarboxylase activity, the conversion of malonate semialdehyde to acetaldehyde and carbon dioxide, the enzyme has now been found to display a promiscuous hydratase activity, converting 2-oxo-3-pentynoate to acetopyruvate, with a kcat/Km value of 6.0 × 102 M-1 s-1. Pro-1 and Arg-75 are critical for both activities, and the pKa of Pro-1 was determined to be ～9.2 by a direct 15N NMR titration. These observations implicate a decarboxylation mechanism in which Pro-1 polarizes the carbonyl oxygen of substrate by hydrogen bonding and/or an electrostatic interaction. Arg-75 may position the carboxylate group into a favorable orientation for decarboxylation. Both the hydratase activity and the pKa value of Pro-1 are shared with trans-3-chloroacrylic acid dehalogenase, another tautomerase superfamily member that precedes MSAD in a bacterial degradation pathway for trans-1,3-dichloropropene. Hence, MSAD and CaaD could have evolved by divergent evolution from a common ancestral protein, retaining the necessary catalytic components for the conjugate addition of water. Copyright

Discovery of α,γ-Diketo Acids as Potent Selective and Reversible Inhibitors of Hepatitis C Virus NS5b RNA-Dependent RNA Polymerase

α,γ-Diketo acids (DKA) were discovered from screening as selective and reversible inhibitors of hepatitis C virus NS5b RNA-dependent RNA polymerase. The diketo acid moiety proved essential for activity, while substitution on the γ position was necessary for selectivity and potency. Optimization led to the identification of a DKA inhibitor of NS5b polymerase with IC50 = 45 nM, one of the most potent HCV NS5b polymerase inhibitors reported.