File:Coumarin_acsv.svg · Wikimedia Commons · See Wikimedia Commons
coumarin
Sign in to saveAlso 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
~11 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “coumarin” article, available under the CC BY-SA 4.0 licence.