4-Hydroxycoumarin

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4-Hydroxycoumarin
Chemical structure of 4-hydroxycoumarin
Names
Preferred IUPAC name
4-Hydroxy-2H-1-benzopyran-2-one
Other names
4-Coumarinol
Benzotetronic acid
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
100.012.783 Edit this at Wikidata
UNII
  • InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H checkY
    Key: VXIXUWQIVKSKSA-UHFFFAOYSA-N checkY
  • InChI=1/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
    Key: PTNLHDGQWUGONS-OWOJBTEDBL
  • Oc1ccc(/C=C/CO)cc1
Properties
C9H6O3
Molar mass 162.144 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

sweet clover silages and is considered a mycotoxin.[1]

4-Hydroxycoumarin is

Anticoagulants

After the identification of dicoumarol and its anticoagulant activity, it became the prototype for a class of drugs. 4-Hydroxycoumarin forms the core of the chemical structure of anticoagulants known collectively as 4-hydroxycoumarins. They include, for example, warfarin, a pharmaceutical drug used to prevent formation of blood clots, and brodifacoum, a widely used rodenticide.

See also

References