Coumalic acid

Base Information

• Chemical Name: Coumalic acid
• CAS No.: 500-05-0
• Molecular Formula: C6H4O4
• Molecular Weight: 140.095
• Hs Code.: 29322090
• European Community (EC) Number: 207-899-0
• NSC Number: 22978
• UNII: OB1JPY343G
• DSSTox Substance ID: DTXSID60870569
• Nikkaji Number: J9.867A
• Wikipedia: Coumalic_acid
• Wikidata: Q19903002
• Metabolomics Workbench ID: 127071
• ChEMBL ID: CHEMBL216734
• Mol file: 500-05-0.mol

Synonyms:Coumalicacid (6CI);Glutaconic acid, 4-(hydroxymethylene)-, d-lactone (7CI);2-Oxo-1(2H)-pyran-5-carboxylic acid;2-Oxo-2H-pyran-5-carboxylic acid;2-Oxopyran-5-carboxylic acid;2-Pentenedioicacid, 4-(hydroxymethylene)-, d-lactone;NSC 22978;a-Pyrone-5-carboxylic acid;

Chemical Property of Coumalic acid

Chemical Property:

• Appearance/Colour: pale yellow to pale brown powder
• Vapor Pressure: 0.000881mmHg at 25°C
• Melting Point: 203-205 °C (dec.)(lit.)
• Refractive Index: 1.4434 (estimate)
• Boiling Point: 282.4 °C at 760 mmHg
• PKA: 2.80±0.20(Predicted)
• Flash Point: 137.3 °C
• PSA: 67.51000
• Density: 1.542 g/cm³
• LogP: 0.33800
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Very soluble in water.
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 140.01095860
• Heavy Atom Count: 10
• Complexity: 236

Purity/Quality:

99% ^*data from raw suppliers

Coumalic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC(=O)OC=C1C(=O)O
• Uses: Coumalic acid undergoes thermal reaction with 1,3-butadiene to yield dimethyl tricycle[3.2.1.02,7]oct-3-ene-2,4-dicarboxylate.

Technology Process of Coumalic acid

There total 12 articles about Coumalic 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: 90.0%

methyl coumalate (6018-41-3) → 2H-pyran-2-one-5-carboxylic acid (500-05-0)

Guidance literature:

With iodine; aluminium; In acetonitrile; at 80 ℃; for 18h;

DOI:10.1021/acs.joc.1c00034

Reference yield: 86.0%

(S)-Malic acid (97-67-6,78644-42-5) → 2H-pyran-2-one-5-carboxylic acid (500-05-0)

Guidance literature:

With trifluorormethanesulfonic acid; In 1,2-dichloro-ethane; at 100 ℃; Reagent/catalyst; Temperature; Solvent; regioselective reaction;

DOI:10.1039/c4ra07105k

Reference yield: 85.0%

malic acid (617-48-1,78644-42-5) → 2H-pyran-2-one-5-carboxylic acid (500-05-0)

Guidance literature:

With sulfuric acid; at 80 - 90 ℃; for 3h;

upstream raw materials:

(S)-Malic acid

(E)-3-Ureido-but-2-enoic acid ethyl ester

malic acid

sulfuric acid

Downstream raw materials:

methyl coumalate

propyl 2-pyrone-5-carboxylate

2-oxo-2H-pyran-5-carbonyl chloride

6-oxo-tetrahydro-pyran-3-carboxylic acid

Refernces

• 1、 Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan. "Cleavage of Carboxylic Esters by Aluminum and Iodine". . p. 4254 - 4261. Retrieved 2021/03/09.
• 2、 -. "A 6 - chloro nicotinic acid preparation method and separation and purification method". Paragraph 0035; 0039-0092. . Retrieved 2017/08/24.