3-Methyl-2-pentenedioic acid

Base Information

• Chemical Name: 3-Methyl-2-pentenedioic acid
• CAS No.: 5746-90-7
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.127
• DSSTox Substance ID: DTXSID80863615
• Mol file: 5746-90-7.mol

Synonyms:3-Methyl-2-pentenedioic acid;3-methylpent-2-enedioic acid;F4N4BX780X;2-Pentenedioic acid, 3-methyl-;NSC 249232;UNII-F4N4BX780X;SCHEMBL27826;DTXSID80863615;AKOS028111125;FT-0694653

Chemical Property of 3-Methyl-2-pentenedioic acid

Chemical Property:

• Vapor Pressure: 1.71E-07mmHg at 25°C
• Melting Point: 115 °C
• Refractive Index: 1.508
• Boiling Point: 399.4 °C at 760 mmHg
• PKA: 4.36±0.10(Predicted)
• Flash Point: 209.5 °C
• PSA: 74.60000
• Density: 1.307 g/cm³
• LogP: 0.49200
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• 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:

99%, ^*data from raw suppliers

3-MethylglutaconicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)O)CC(=O)O
• Uses: 3-Methylglutaconic acid is a glutarate which builds up in the urine in 3-methylglutaconic aciduria. 3-methylglutaconic aciduria is a term used to describe five different disorders that impair the functioning of energy-producing centers within cells (mitochondria)

Technology Process of 3-Methyl-2-pentenedioic acid

There total 10 articles about 3-Methyl-2-pentenedioic 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: 98.0%

isodehydracetic acid (480-65-9) → 3-methylpent-2-enedioic acid (372-42-9,15649-56-6,5746-90-7)

Guidance literature:

With potassium hydroxide; at 22 - 23 ℃;

DOI:10.1055/s-1993-35864

Reference yield: 95.0%

ethyl isodehydroacetate (3385-34-0) → 3-methylpent-2-enedioic acid (372-42-9,15649-56-6,5746-90-7)

Guidance literature:

With sodium hydroxide; In water; at 70 ℃; for 1h;

DOI:10.1016/S0040-4020(01)91537-6

Reference yield: 22.0%

ethyl acetoacetate (141-97-9) → 3-methylpent-2-enedioic acid (372-42-9,15649-56-6,5746-90-7)

Guidance literature:

ethyl acetoacetate; With sulfuric acid;

With sodium hydroxide; In water;

DOI:10.1021/ic301631n

upstream raw materials:

3-methyl-pentenedioic acid monoethyl ester

diethyl 3-methylpent-2-enedioate

5-acetyl-1,6-dihydroxy-4-methyl-2(1H)-pyridone

isodehydracetic acid

Downstream raw materials:

3-methyl-pentenedioic acid anhydride

(E)-3-methylpent-2-enedioic acid

3-methyl-2-pentene-1,5-diacid dimethyl

(1S,2R)-tert-butyl 5-methyl-2',3-dioxo-1-phenylspiro[cyclohex[4]ene-2,3'-indoline]-1'-carboxylate

Refernces

• 1、 -. "POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES". Page/Page column 52; 53. . Retrieved 2016/06/06.
• 2、 Kuchkova,Morari,Vlad. "An improved synthesis of a mixture of diethyl (Z)- and (E)-3-methylglutaconates from ethyl acetoacetate". . p. 1221 - 1222. Retrieved 2007/10/02.