Mesaconic acid

Base Information

• Chemical Name: Mesaconic acid
• CAS No.: 498-24-8
• Molecular Formula: C5H6 O4
• Molecular Weight: 130.1
• Hs Code.: 2917190090
• European Community (EC) Number: 207-859-2
• NSC Number: 65438,32949
• UNII: 90UTM639KK
• DSSTox Substance ID: DTXSID10883407
• Nikkaji Number: J278.813F,J6.107G
• Wikipedia: Mesaconic_acid
• Wikidata: Q3544981
• Metabolomics Workbench ID: 2028
• Mol file: 498-24-8.mol

Synonyms:(E)-2-methyl-2-butenedioic acid;(Z)-2-methyl-2-butenedioic acid;citraconic acid;citraconic acid, (E)-isomer;citraconic acid, ammonium salt;citraconic acid, calcium salt;citraconic acid, sodium salt;mesaconic acid;methylfumaric acid;methylmaleic acid;monomethylfumarate

Chemical Property of Mesaconic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 200-202 ºC
• Refractive Index: 1.4240 (estimate)
• Boiling Point: 336.6 °C at 760 mmHg
• PKA: 3.09(at 25℃)
• Flash Point: 171.5 °C
• PSA: 74.60000
• Density: 1.387 g/cm³
• LogP: 0.10190
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 26.3g/L(18 oC)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 130.02660867
• Heavy Atom Count: 9
• Complexity: 168

Purity/Quality:

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

Mesaconic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CC(=O)O)C(=O)O
• Isomeric SMILES: C/C(=C\C(=O)O)/C(=O)O
• Uses: Mesaconic acid is used in electropolishing stainless steel and as a laminant for polyethylene. Mesaconic Acid activates dopamine β-mono-oxygenase.

Technology Process of Mesaconic acid

There total 96 articles about Mesaconic 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: 68.0%

2-methylenesuccinic acid (97-65-4,25119-64-6) → poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) + citraconic acid (498-23-7,7407-59-2) + Mesaconic acid (498-24-8,7407-59-2)

Guidance literature:

With 5% Pt/Al2O3; sodium hydroxide; In water; at 250 ℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;

DOI:10.1002/cssc.201402117

Reference yield: 24.1%

citric acid (77-92-9,906507-37-7) → poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) + citraconic acid (498-23-7,7407-59-2) + Mesaconic acid (498-24-8,7407-59-2) + 2-methylenesuccinic acid (97-65-4,25119-64-6)

Guidance literature:

With 4-methoxy-phenol; triphenylphosphine; In water; at 225 ℃; for 1.5h; under 20686.5 Torr; Temperature; Glovebox; Inert atmosphere;

Reference yield:

citric acid (77-92-9,906507-37-7) → poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) + Mesaconic acid (498-24-8,7407-59-2) + 2-methylbutanedioic acid (498-21-5,636-60-2) + 2-methylenesuccinic acid (97-65-4,25119-64-6) + acetic acid (64-19-7,77671-22-8) + 2-oxo-propionic acid (127-17-3) + acetone (67-64-1)

Guidance literature:

With hydrogen; In water; at 225 ℃; for 0.666667h; under 15001.5 Torr;

upstream raw materials:

3-bromo-4-methyl-2,5-furandione

ethanol

citraconic acid

2-methyl-fumaramide

Downstream raw materials:

2-methylenesuccinic acid

citraconic acid

2-methylbutanedioic acid

(S)-citramalic acid

Refernces

• 1、 Botting, Nigel P.,Jackson, Alan A.,Gani, David. "15N-Isotope and Double Isotope Fractionation Studies of the Mechanism of 3-Methylaspartase: Concerted Elimination of Ammonia from (2S,3S)-3-Methylaspartic Acid". . p. 1583 - 1585. Retrieved 1989.
• 2、 -. "Methacrylic acid production method". Page/Page column 9; 14-15. . Retrieved 2018/12/11.
• 3、 -. "METHOD FOR THE PRODUCTION OF METHYLSUCCINIC ACID AND THE ANHYDRIDE THEREOF FROM CITRIC ACID". Page/Page column 15. . Retrieved 2018/04/21.