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Coumarin
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| Names | |
|---|---|
| IUPAC name
2H-Chromen-2-one
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| Preferred IUPAC name
2H-1-Benzopyran-2-one | |
| Other names
1-Benzopyran-2-one
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| Identifiers | |
3D model (JSmol)
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| 383644 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.001.897 |
| EC Number |
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| 165222 | |
| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA)
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| 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)) |
| −82.5×10−6 cm3/mol | |
| Structure | |
| orthorhombic | |
| Hazards | |
| GHS labelling: | |
 
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| 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) | |
| Flash point | 150 °C (302 °F; 423 K) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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293 mg/kg (rat, oral) |
| Safety data sheet (SDS) | Sigma-Aldrich |
| Related compounds | |
Related compounds
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Chromone; 2-Cumaranone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1]
Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste.[1] It is found in many plants, where it may serve as a chemical defense against predators. While coumarin is not an anticoagulant, its 3-hydroxy-4-alkyl derivatives, such as the fungal metabolite dicoumarol, inhibit synthesis of vitamin K, a key component in blood clotting.[2] A related compound, the prescription drug anticoagulant warfarin, is used to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism.[1][3]
- ^ a b c "Coumarin". PubChem, National Library of Medicine, US National Institutes of Health. 4 April 2019. Retrieved 13 April 2019.
- ^ Low Dog, Tieraona; Markham, Merry Jennifer (2007). "Dietary Supplements and Hemostasis". Consultative Hemostasis and Thrombosis (2nd ed.). Philadelphia, PA: Elsevier Health Sciences. p. 564. doi:10.1016/B978-141602401-9.10033-1. ISBN 9781437710601.
- ^ "Coumarins and indandiones". Drugs.com. 2016. Retrieved 24 December 2016.
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