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

Description

2,4-dioxovaleric acid, also known as acetylpyruvic acid, is a derivative of pyruvic acid, which is an intermediate in sugar metabolism and enzymatic carbohydrate degradation. It plays a crucial role in various metabolic processes, including the conversion of pyruvic acid to acetaldehyde and CO2 during alcoholic fermentation, and the reduction of pyruvic acid to lactic acid in muscle during exertion.

Uses

Used in Diagnostic Applications:
2,4-dioxovaleric acid is used as a diagnostic agent for Parkinson's disease, helping to identify and monitor the progression of the condition.
Used in Metabolic Processes:
In muscle, 2,4-dioxovaleric acid is involved in the conversion of pyruvic acid to lactic acid during exertion, which is then reoxidized and partially retransformed to glycogen during rest.
Used in Liver Metabolism:
In the liver, 2,4-dioxovaleric acid plays a role in the conversion of pyruvic acid to alanine through amination, contributing to the regulation of amino acid levels in the body.

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.