Coumarin

Coumarin

Names
IUPAC name 2H-chromen-2-one
Other names 1-benzopyran-2-one
Identifiers
CAS Number	91-64-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28794 Y
ChEMBL	ChEMBL6466 Y
ChemSpider	13848793 Y
DrugBank	DB04665 Y
ECHA InfoCard	100.001.897
EC Number	202-086-7
KEGG	D07751 Y
PubChem	323
RTECS number	GN4200000
UNII	A4VZ22K1WT Y
InChI 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 c1ccc2c(c1)ccc(=O)o2
Properties
Chemical formula	C9H6O2
Molar mass	146.15 g·mol−1
Appearance	colorless to white crystals
Odor	pleasant, like vanillabeans
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)	3004175000000000000♠−82.5×10−6 cm3/mol
Structure
Crystal structure	orthorhombic
Hazards
Safety data sheet	Sigma-Aldrich
NFPA 704	1 2 0
Flash point	150 °C (302 °F; 423 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	293 mg/kg (rat, oral)
Related compounds
Related compounds	Chromone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Coumarin (/ˈkuːmərɪn/; 2H-chromen-2-one) is a fragrant organic chemical compound in the benzopyrone chemical class, which is a colorless crystalline substance in its standard state. It is a natural substance found in many plants.

The name comes from a French term for the tonka bean, coumarou, one of the sources from which coumarin was first isolated as a natural product in 1820. It has a sweet odor, readily recognised as the scent of newly-mown hay, and has been used in perfumes since 1882. Sweet woodruff, meadowsweet, sweet grass and sweet-clover in particular are named for their sweet (i.e., pleasant) smell, which in turn is due to their high coumarin content. When it occurs in high concentrations in forage plants, coumarin is a somewhat bitter-tasting appetite suppressant, and is presumed to be produced by plants as a defense chemical to discourage predation.

Coumarin is used in certain perfumes and fabric conditioners. Coumarin has been used as an aroma enhancer in pipe tobaccos and certain alcoholic drinks, although in general it is banned as a flavorant food additive, due to concerns regarding its hepatotoxicity in animal models.

Coumarin was first synthesized in 1868. It is used in the pharmaceutical industry as a precursor reagent in the synthesis of a number of synthetic anticoagulant pharmaceuticals similar to dicoumarol, the notable ones being warfarin (brand name Coumadin) and some even more potent rodenticides that work by the same anticoagulant mechanism. 4-hydroxycoumarins are a type of vitamin K antagonist. Pharmaceutical (modified) coumarins were all developed from the study of sweet clover disease; see warfarin for this history. However, unmodified coumarin itself, as it occurs in plants, has no effect on the vitamin K coagulation system, or on the action of warfarin-type drugs.