Basic information
- CAS
500-05-0- Standard SMILES
O=C(O)c1ccc(=O)oc1- InChIKey
ORGPJDKNYMVLFL-UHFFFAOYSA-N- Molecular formula
- C6H4O4
- Average molar mass
- 140.09 g/mol
- Monoisotopic mass
- 140.01095861
Overview
Coumalic acid is a pyranone.
Names & identifiers
- Preferred name
- Coumalic acid
- IUPAC
- 6-oxopyran-3-carboxylic acid
- English name
- Coumalic acid
- Molecular formula
- C6H4O4
- Molecular weight
- 140.09
Names & synonyms
Coumalic acid500-05-0Cumalic acid2H-Pyran-5-carboxylic acid, 2-oxo-2-Oxopyran-5-carboxylic acidalpha-Pyrone-5-carboxylic acidOB1JPY343GNSC-229782-Oxo-1,2H-pyran-5-carboxylic acidDTXSID608705692-Pentenedioic acid, 4-(hydroxymethylene)-, delta-lactoneRefChem:579295
Show more names
courMaric acidDilzenDilticardCUMALINIC ACIDCoumalicacid,97%CouMalic acid 97%Coumalic Acid >
DTXCID20818280207-899-02-Oxo-2H-pyran-5-carboxylic acid6-oxopyran-3-carboxylic acidMFCD000066442-Pyrone-5-carboxylic acid.alpha.-Pyrone-5-carboxylic acidCoumalicacid
Database identifiers
- CAS
500-05-0- PubChem CID
- 68141
- DTXSID
DTXSID60870569- ChEMBL
CHEMBL216734- ChEBI
CHEBI:180952- UNII
- OB1JPY343G
- EC Number
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 63.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 236
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Organic Acids
Physical DescriptionBright yellow solid; [Merck Index] Pale yellow or light brown powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 203 · 203-205 °C (dec.) (lit.)
- Boiling point
- 218 °C/120 · 218 °C/120 mmHg (lit.)
- Density
- 1.2154 · 1.2154 (rough estimate)
- refractive index
- 1.4434 · 1.4434 (estimate)
- Flash point
- 218 °C/120mm · 218°C/120mm
- storage temp.
- Sealed in dry,Room Temperature
- form
- powder to crystal
- pka
- 2.8 · 2.80±0.20(Predicted)
- color
- White to Light yellow to Light orange
- Water Solubility
- Very soluble in water.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29322090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2H-Pyran-5-carboxylic acid, 2-oxo-: INACTIVE
Applications
UsesCoumalic acid undergoes thermal reaction with 1,3-butadiene to yield dimethyl tricycle[3.2.1.02,7]oct-3-ene-2,4-dicarboxylate.
General DescriptionDecarboxylates to α-pyrone, a Diels-Alder diene.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
4 records
Compound notes
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