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Coumarin (/ ˈ k uː m ər ɪ n /) or 2H-chromen-2-one is an aromatic organic chemical compound with formula C 9 H 6 O 2.Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring.
Warning label on a tube of rat poison containing bromadiolone on a dike of the Scheldt river in Steendorp, Belgium. Bromadiolone is a potent anticoagulant rodenticide.It is a second-generation 4-hydroxycoumarin derivative and vitamin K antagonist, often called a "super-warfarin" for its added potency and tendency to accumulate in the liver of the poisoned organism.
Brodifacoum is a 4-hydroxycoumarin anticoagulant, with a similar mode of action to its historical predecessors dicoumarol and warfarin.However, due to very high potency and long duration of action (elimination half-life of 20 – 130 days), it is characterised as a "second-generation" or "superwarfarin" anticoagulant.
Coumarin is known to cause liver and kidney damage in high concentrations and metabolic effect in humans with CYP2A6 polymorphism. [73] [74] Based on this assessment, the European Union set a guideline for maximum coumarin content in foodstuffs of 50 mg per kg of dough in seasonal foods, and 15 mg per kg in everyday baked foods. [75]
Phenprocoumon (marketed under the brand names Marcoumar, Marcumar and Falithrom) is a long-acting anticoagulant to be taken by mouth, and a coumarin derivative. [2] It acts as a vitamin K antagonist and inhibits blood clotting (coagulation) by blocking synthesis of coagulation factors II, VII, IX and X.
Coumarin (1-benzopyran-2-one) Certain simple benzopyrones have clinical medical value as an edema modifiers. Coumarin and other benzopyrones, such as 5,6 benzopyrone, 1,2 benzopyrone, diosmin and others are known to stimulate macrophages to degrade extracellular albumin, allowing faster resorption of edematous fluids. [1] [2]
Coumarin dyes are extensively used as gain media in blue-green tunable organic dye lasers. [14] [15] [16] Among the various coumarin laser dyes are coumarins 480, 490, 504, 521, 504T, and 521T. [16] Coumarin tetramethyl laser dyes offer wide tunability and high laser gain, [17] [18] and they are also used as active medium in coherent OLED emitters.
It is also involved in the metabolism of several pharmaceuticals, carcinogens, and a number of coumarin-type alkaloids. CYP2A6 is the only enzyme in the human body that appreciably catalyzes the 7-hydroxylation of coumarin , such that the formation of the product of this reaction, 7-hydroxycoumarin, is used as a probe for CYP2A6 activity.