4-hydroxycoumarin
Sign in to saveAlso known as 4-coumarinol, 4-Hydroxy-1-Benzopyran-2-One, 4-hydroxy-2H-1-benzopyran-2-one, 4-hydroxychromen-2-one, benzotetronic acid, 4-hydroxy-2H-chromen-2-one, 4-hydroxy-2-chromenone, 4-hydroxy-2H-benzo[b]pyran-2-one
4-Hydroxycoumarin is a coumarin derivative with a hydroxy group at the 4-position.
Wikidata facts
- Mass
- 162.032
Show 4 more facts
- found in taxon
- Ruta graveolens
- canonical SMILES
- C1=CC=C2C(=C1)C(=CC(=O)O2)O
- chemical formula
- C₉H₆O₃
- Commons category
- 4-Hydroxycoumarin
via Wikidata · CC0
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Encyclopedic overview
4 sectionsContents
- Occurrence
- Anticoagulants
- See also
- References
4-Hydroxycoumarin is a coumarin derivative with a hydroxy group at the 4-position.
==Occurrence== 4-Hydroxycoumarin is an important fungal metabolite from the precursor coumarin, and its production leads to further fermentative production of the natural anticoagulant dicoumarol. This happens in the presence of naturally occurring formaldehyde, which allows attachment of a second 4-hydroxycoumarin molecule through the linking carbon of the formaldehyde, to the 3-position of the first 4-hydroxycoumarin molecule, to give the semi-dimer the motif of the drug class. Dicoumarol appears as a fermentation product in spoiled sweet clover silages and is considered a mycotoxin.
Excerpted from Wikipedia’s “4-hydroxycoumarin” article, available under the CC BY-SA 4.0 licence.