coumarin
Also known as 2H-benzo[b]pyran-2-one, o-hydroxycinnamic acid delta-lactone, 2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone, Coumarine, Benzo-alpha-pyrone, chromen-2-one, 2-Oxo-2H-1-Benzopyran, 2-Oxo-1,2-benzopyran
Coumarin () or '2H-chromen-2-one' is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring , 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.
Chemical data
- Formula
- C9H6O2
- Molecular weight
- 146.14 g/mol
- IUPAC name
- chromen-2-one
- SMILES
- C1=CC=C2C(=C1)C=CC(=O)O2
- InChIKey
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
- XLogP
- 1.4
- Polar surface area
- 26.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Image
- Coumarin sample.jpg
~11 min read
Article
12 sectionsContents
- Etymology
- History
- Synthesis
- Biosynthesis
- Natural occurrence
- Biological function
- Metabolism
- Derivatives
- Uses
- Toxicity
- Notes
- References
Coumarin () or '2H-chromen-2-one' is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring , 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.