2-Hydroxy-3-oxobutanedioic acid

Base Information

• Chemical Name: 2-Hydroxy-3-oxobutanedioic acid
• CAS No.: 5651-05-8
• Molecular Formula: C₄H₄O₆
• Molecular Weight: 148.072
• DSSTox Substance ID: DTXSID30861787
• Nikkaji Number: J1.796.992G
• Wikidata: Q27102603
• Mol file: 5651-05-8.mol

Synonyms:Oxaloglycolate;2-hydroxy-3-oxobutanedioic acid;2-hydroxy-3-oxosuccinic acid;OXALOGLYCOLIC ACID;C03459;SCHEMBL1291687;CHEBI:17778;DTXSID30861787;BDBM50390677;AKOS006377432;Q27102603

Chemical Property of 2-Hydroxy-3-oxobutanedioic acid

Chemical Property:

• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 148.00078784
• Heavy Atom Count: 10
• Complexity: 182

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(=O)C(=O)O)(C(=O)O)O

Technology Process of 2-Hydroxy-3-oxobutanedioic acid

There total 2 articles about 2-Hydroxy-3-oxobutanedioic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tartaric acid (87-69-4,138508-61-9) → 2,3-dioxo-propionic acid (815-53-2) + 2-hydroxy-3-oxopropanoic acid (2480-77-5) + acetonedicarboxylic acid (473-90-5) + 2-hydroxy-3-oxosuccinic acid (5651-05-8)

Guidance literature:

With oxygen; ozone; In water; at 20 ℃; Flow reactor;

DOI:10.1021/acs.jpca.6b05289

Reference yield:

D-Fructose (57-48-7,18875-34-8) → glycolic Acid (79-14-1) + 2-hydroxy-3-oxosuccinic acid (5651-05-8) + (2R,3S,4S)-2-Hydroxymethyl-dihydro-pyran-2,3,4,5,5-pentaol (73960-91-5) + β-D-arabino-hex-2-ulopyranosonic acid (72933-33-6) + (2S,3S,4S)-2,3,4,5,5-Pentahydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:

With oxygen; platinum on activated charcoal; at 30 ℃; under 152 Torr; Product distribution; various reaction times, amount of catalyst, effect of addition of NaOH and HMTA; other catalysts;

DOI:10.1016/S0008-6215(97)10003-9

Reference yield:

2-hydroxy-3-oxosuccinic acid (5651-05-8) → acetonedicarboxylic acid (473-90-5) + oxalic acid (144-62-7,97993-78-7)

Guidance literature:

With oxygen; In water; at 25 ℃; Thermodynamic data; E(excit.), effects of pH, effects of O₂;

upstream raw materials:

D-Fructose

tartaric acid

Downstream raw materials:

Glycolaldehyde

acetonedicarboxylic acid

oxalic acid