4-Oxohex-2-enedioate

Base Information

• Chemical Name: 4-Oxohex-2-enedioate
• CAS No.: 24740-88-3
• Molecular Formula: C₆H₆O₅
• Molecular Weight: 158.111
• UNII: JAD9FA3JG6
• DSSTox Substance ID: DTXSID001029401
• Metabolomics Workbench ID: 52848
• Nikkaji Number: J847.097I
• Wikidata: Q76280924
• Wikipedia: Maleylacetic_acid
• Mol file: 24740-88-3.mol

Synonyms:maleoylacetic acid;maleylacetate

Chemical Property of 4-Oxohex-2-enedioate

Chemical Property:

• Vapor Pressure: 1.84E-08mmHg at 25°C
• Boiling Point: 426.3°C at 760 mmHg
• Flash Point: 225.7°C
• PSA: 91.67000
• Density: 1.469g/cm³
• LogP: -0.32900
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 158.02152329
• Heavy Atom Count: 11
• Complexity: 215

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

Technology Process of 4-Oxohex-2-enedioate

There total 7 articles about 4-Oxohex-2-enedioate 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: 35.0%

hydroquinone (123-31-9,8027-02-9) → 2-keto-cis,cis-muconic acid (374932-25-9) + 4-hydroxy-cis,cis-muconic acid + C6H6O4 + 3-keto-cis,cis-muconic acid (24740-88-3)

Guidance literature:

With Pseudomonas sp. isolated from coastal waters and soils of the Absheron peninsula at the Caspian Sea; In water; at 28 ℃; Microbiological reaction;

DOI:10.1134/S0965544113050101

Reference yield:

p-chloro-o-nitrophenol (89-64-5) → 4-oxo-hex-2t-enedioic acid (31571-51-4,24740-88-3)

Guidance literature:

With sulfuric acid; at 110 - 120 ℃; Anschliessende Reduktion mit verkupfertem Zink in verd. H₂SO₄;

Reference yield:

(Z)-5-oxo-2,5-dihydrofuran-2-ylideneacetic acid (3374-46-7,22752-92-7,73237-79-3,18529-79-8) → 3-keto-cis,cis-muconic acid (24740-88-3)

Guidance literature:

With dienelactone hydrolase (EC 3.1.1.45); water; at 24.85 ℃; pH=7.0; Further Variations:; Reagents; Kinetics;

DOI:10.1039/b000365o

upstream raw materials:

p-chloro-o-nitrophenol

2-bromobenzene-1,4-diol

chloro-p-hydroquinone

(Z)-5-oxo-2,5-dihydrofuran-2-ylideneacetic acid