3,4-Didehydro-2-ketoglutaric acid

Base Information

• Chemical Name: 3,4-Didehydro-2-ketoglutaric acid
• CAS No.: 6004-32-6
• Molecular Formula: C5H4 O5
• Molecular Weight: 144.084
• Hs Code.: 2918300090
• Nikkaji Number: J761.839E
• ChEMBL ID: CHEMBL4847806
• Mol file: 6004-32-6.mol

Synonyms:2-oxoglutaconic acid;3,4-didehydro-2-ketoglutaric acid;3-ene-2-ketoglutarate

Chemical Property of 3,4-Didehydro-2-ketoglutaric acid

Chemical Property:

• Vapor Pressure: 3.23E-05mmHg at 25°C
• Boiling Point: 330.5°C at 760 mmHg
• Flash Point: 167.9°C
• PSA: 91.67000
• Density: 1.582
• LogP: -0.71910
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 144.00587322
• Heavy Atom Count: 10
• Complexity: 202

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(=CC(=O)O)C(=O)C(=O)O
• Isomeric SMILES: C(=C/C(=O)O)\C(=O)C(=O)O

Technology Process of 3,4-Didehydro-2-ketoglutaric acid

There total 5 articles about 3,4-Didehydro-2-ketoglutaric 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: 40.0%

dimethyl (E)-2-oxoglutaconate (38256-25-6) → (E)-4-oxopent-2-enedioic acid (6004-32-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2021.116141

Reference yield:

dimethyl 2-chloro-4-methylenepentanedioate → (E)-4-oxopent-2-enedioic acid (6004-32-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrachloromethane; sodium periodate; ruthenium tetroxide / acetonitrile

2: lithium hydroxide / tetrahydrofuran / 2 h / 20 °C

With tetrachloromethane; sodium periodate; ruthenium tetroxide; lithium hydroxide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.bmc.2021.116141

Reference yield:

3-Keto-4.5-dideoxy-trans-4.5-dehydro-glucuronsaeure → (E)-4-oxopent-2-enedioic acid (6004-32-6)

Guidance literature:

With periodic acid;

upstream raw materials:

D-glucurono-6,3-lactone

dimethyl (E)-2-oxoglutaconate

Refernces

• 1、 Ishidate,Kimura,Kawata. "A new reductone derived from D-glucuronolatone, 3-keto-4,5-dideoxy-trans-4,5-dehydroglucuronic acid.". . p. 1083 - 1084. Retrieved 2007/10/09.