| Coumarin | |
|---|---|
| Chemical name | 1,2-Benzopyrone 2H-1-Benzopyran-2-one |
| Chemical formula | C9H6O2 |
| Molecular mass | 146.14 g/mol |
| Melting point | 71 °C |
| Boiling point | 301 °C |
| Density | 0.935 g/cm³ (20 °C) |
| CAS number | 91-64-5 |
| SMILES | |
| File:Cumarin.jpg | |
| Disclaimer and references | |
Coumarin is a chemical compound found in many plants, notably in high concentration in the tonka bean, woodruff, and sweetgrass. It has a sweet scent, readily recognised as the scent of newly-mown grass. It has clinical value as the precursor for several anticoagulants, notably warfarin. It is also used as a gain medium in some dye lasers.
Coumarin is often found in tobacco products and artificial vanilla substitutes, though it has been banned as a food additive in numerous countries since the mid-20th century because it is moderately toxic to the liver and kidneys. It is also slightly carcinogenic.
Synthesis
The biosynthesis of coumarin in plants is via hydroxylation, glycolysis and cyclisation of cinnamic acid. Coumarin can be prepared in a laboratory in a Perkin reaction between salicylaldehyde and acetic anhydride.
The Pechmann condensation provides another synthesis of coumarin and its derivatives.
Derivatives
Some naturally occuring coumarin derivatives include umbelliferone (7-hydroxycoumarin), herniarin (7-methoxycoumarin), psoralen and imperatorin.