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Coumarin

Coumarin
Coumarin acsv.svg
Coumarin.png
Coumarin spacefill.png
Names
IUPAC name
2H-chromen-2-one
Other names
1-benzopyran-2-one
Identifiers
91-64-5 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:28794 YesY
ChEMBL ChEMBL6466 YesY
ChemSpider 13848793 YesY
DrugBank DB04665 YesY
ECHA InfoCard 100.001.897
EC Number 202-086-7
KEGG D07751 YesY
PubChem 323
RTECS number GN4200000
UNII A4VZ22K1WT YesY
Properties
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)
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))
−82.5×10−6 cm3/mol
Structure
orthorhombic
Hazards
Safety data sheet Sigma-Aldrich
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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).
YesY  (what is YesYN ?)
Infobox references

Coumarin (/ˈkmərɪn/; 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.


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