Coumarin

Coumarin
Names
	IUPAC name 2H-Chromen-2-one
	Preferred IUPAC name 2H-1-Benzopyran-2-one
	Other names 1-Benzopyran-2-one
Identifiers
CAS Number	91-64-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	383644
ChEBI	CHEBI:28794 ;
ChEMBL	ChEMBL6466 ;
ChemSpider	13848793 ;
DrugBank	DB04665 ;
ECHA InfoCard	100.001.897
EC Number	202-086-7;
Gmelin Reference	165222
KEGG	D07751 ;
PubChem CID	323;
RTECS number	GN4200000;
UNII	A4VZ22K1WT ;
CompTox Dashboard (EPA)	DTXSID7020348 ;
	InChI InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H Key: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N ; 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
Chemical formula	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)
Solubility in water	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
Crystal structure	orthorhombic
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H373
Precautionary statements	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). verify (what is ?) Infobox references

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 is considered a lactone.

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. While coumarin is not an anticoagulant, its 3-alkyl-4-hydroxy derivatives, such as the fungal metabolite dicoumarol, inhibit 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.