From Wikipedia, the free encyclopedia
  (Redirected from 4-hydroxycoumarin)
Jump to: navigation, search
This article is about the chemical compound. For the class of drugs derived from it, see 4-Hydroxycoumarins.
Chemical structure of 4-hydroxycoumarin
IUPAC name
Other names
Benzotetronic acid
1076-38-6 YesY
3D model (Jmol) Interactive image
Interactive image
ChEMBL ChEMBL301141 YesY
ChemSpider 10254753 YesY
ECHA InfoCard 100.012.783
PubChem 14101
Molar mass 162.14 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

4-Hydroxycoumarin is a coumarin derivative with a hydroxy group at the 4-position.


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.[1]

4-Hydroxycoumarin is biosynthesized from malonyl-CoA and 2-hydroxybenzoyl-CoA by the enzyme 4-hydroxycoumarin synthase.[2]


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.


  1. ^ Bye, A.; King, H. K. (1970). "The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius". Biochemical Journal. 117 (2): 237–245. doi:10.1042/bj1170237. PMC 1178855Freely accessible. PMID 4192639. 
  2. ^ Liu, B.; Raeth, T.; Beuerle, T. & Beerhues, L. (2010). "A novel 4-hydroxycoumarin biosynthetic pathway". Plant Mol. Biol. 72 (1–2): 17–25. doi:10.1007/s11103-009-9548-0. PMID 19757094.