Coumarin

Coumarin (/ˈkuːmərɪn/) or 2H-chromen-2-one is an aromatic organic chemical compound with formula C9H6O2. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It belongs to the benzopyrone chemical class and considered as a lactone.

This article is about the compound. For the anticoagulants and rodenticides called "coumarins" or "coumadins", see 4-Hydroxycoumarins. For other uses, see Coumarin derivatives.
Coumarin
Names
IUPAC name
2H-Chromen-2-one
Preferred IUPAC name
2H-1-Benzopyran-2-one
Other names
1-Benzopyran-2-one
Identifiers
3D model (JSmol)
383644
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.897
EC Number
  • 202-086-7
165222
KEGG
PubChem CID
RTECS number
  • GN4200000
UNII
  • InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H Y
    Key: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N Y
  • InChI=1/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
    Key: ZYGHJZDHTFUPRJ-UHFFFAOYAC
SMILES
  • O=C1C=Cc2ccccc2O1
Properties
C9H6O2
Molar mass 146.145 g·mol−1
Appearance colorless to white crystals
Odor pleasant, like vanilla beans
Density 0.935 g/cm3 (20 °C (68 °F))
Melting point 71 °C (160 °F; 344 K)
Boiling point 301.71 °C (575.08 °F; 574.86 K)
0.17 g / 100 mL
Solubility very soluble in ether, diethyl ether, chloroform, oil, pyridine
soluble in ethanol
log P 1.39
Vapor pressure 1.3 hPa (106 °C (223 °F))
Magnetic susceptibility (χ)
 −82.5×10−6 cm3/mol
Structure
orthorhombic
Hazards
GHS labelling:
Warning
H302, H317, H373
P260, P261, P264, P270, P272, P280, P301+P312, P302+P352, P314, P321, P330, P333+P313, P363, P501
NFPA 704 (fire diamond)
2
1
0
Flash point 150 °C (302 °F; 423 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 293 mg/kg (rat, oral)
Safety data sheet (SDS) Sigma-Aldrich
Related compounds
Related compounds
 Chromone; 2-Cumaranone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste. It is found in many plants, where it may serve as a chemical defense against predators. Coumarin inhibits synthesis of vitamin K, a key component in blood clotting. A related compound, the prescription drug anticoagulant warfarin, is used to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism.

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