(E)-2-Methylglutaconic acid

Base Information

• Chemical Name: (E)-2-Methylglutaconic acid
• CAS No.: 53358-21-7
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.127
• DSSTox Substance ID: DTXSID601009869
• Wikidata: Q76324550
• Metabolomics Workbench ID: 2000
• Mol file: 53358-21-7.mol

Synonyms:(E)-2-methylglutaconic acid;1-methyl-1-propene-1,3-dicarboxylic acid;2-methylglutaconic acid

Chemical Property of (E)-2-Methylglutaconic acid

Chemical Property:

• Vapor Pressure: 1.71E-07mmHg at 25°C
• Melting Point: 141-147°C
• Boiling Point: 399.4°Cat760mmHg
• Flash Point: 209.5°C
• PSA: 74.60000
• Density: 1.307g/cm³
• LogP: 0.49200
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 180

Purity/Quality:

98%,99%, ^*data from raw suppliers

(E)-2-Methylglutaconic acid ≥98.0% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (E)-2-Methylglutaconic acid

There total 3 articles about (E)-2-Methylglutaconic 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: 62.0%

1,1,3,3-tetracarboethoxybutene (56298-73-8) → (E)-γ-methylglutaconic acid (53358-21-7,57071-29-1)

Guidance literature:

With potassium hydroxide; In water; for 3h; Reflux;

DOI:10.1016/j.tet.2015.05.052

Reference yield:

sodio-1,1,3,3-tetracarboethoxypropene (56298-72-7) → (E)-γ-methylglutaconic acid (53358-21-7,57071-29-1)

Guidance literature:

Multi-step reaction with 2 steps

2: aq. KOH

With potassium hydroxide;

DOI:10.1021/jo00909a016

Reference yield:

dimethyl 2-methylenepentanedioate (5621-44-3) → (E)-γ-methylglutaconic acid (53358-21-7,57071-29-1)

Guidance literature:

Multistep reaction; (i) RhCl₃, benzene-1,4-diol, EtOH, (ii) aq. NaOH;

DOI:10.1002/hlca.19740570343

upstream raw materials:

dimethyl 2-methylenepentanedioate

1,1,3,3-tetracarboethoxybutene

sodio-1,1,3,3-tetracarboethoxypropene

Downstream raw materials:

(Z)-γ-methylglutaconic acid