Coumarin derivatives are derivatives of coumarin and are considered phenylpropanoids. Among the most important derivatives are the 4-hydroxycoumarins, which exhibit anticoagulant properties, a characteristic not present for coumarin itself. Some naturally occurring coumarin derivatives include umbelliferone (7-hydroxycoumarin), aesculetin (6,7-dihydroxycoumarin), herniarin (7-methoxycoumarin),

psoralen Psoralen (also called psoralene) is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. It is structurally related to coumarin by the addition of a fused furan ring, and may be considered a ...

and imperatorin. 4-Phenylcoumarin is the backbone of the neoflavones, a type of neoflavonoids. Coumarin pyrazole hybrids have been synthesized from hydrazones, carbazones and thiocarbazones via Vilsmeier Haack formylation reaction. Compounds derived from coumarin are also called coumarins or coumarinoids; this family includes: * brodifacoum * bromadiolone * difenacoum * auraptene * ensaculin *

phenprocoumon Phenprocoumon (marketed under the brand names Marcoumar, Marcumar and Falithrom) is a long-acting anticoagulant to be taken by mouth, and a coumarin derivative. It acts as a vitamin K antagonist and inhibits blood clotting (coagulation) by blocki ...

(Marcoumar) * PSB-SB-487 * PSB-SB-1202 * scopoletin can be isolated from the bark of ''Shorea pinanga'' * warfarin (Coumadin) Coumarin is transformed into the natural anticoagulant dicoumarol by a number of species of

fungi A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one ...

. This occurs as the result of the production of 4-hydroxycoumarin, then further (in the presence of naturally occurring formaldehyde) into the actual anticoagulant dicoumarol, a fermentation product and mycotoxin. Dicoumarol was responsible for the bleeding disease known historically as " sweet clover disease" in cattle eating moldy sweet clover silage. In basic research, preliminary evidence exists for coumarin having various biological activities, including anti-inflammatory, anti-tumor, antibacterial, and antifungal properties, among others.

Uses

Medicine

Warfarin – a coumarin – with

brand name A brand is a name, term, design, symbol or any other feature that distinguishes one seller's goods or service from those of other sellers. Brands are used in business, marketing, and advertising for recognition and, importantly, to create and ...

, ''Coumadin'', is a prescription drug used as an anticoagulant to inhibit formation of blood clots, and so is a

therapy A therapy or medical treatment is the attempted remediation of a health problem, usually following a medical diagnosis. Both words, ''treatment'' and ''therapy'', are often abbreviated tx, Tx, or Tx. As a rule, each therapy has indications a ...

for deep vein thrombosis and

pulmonary embolism Pulmonary embolism (PE) is a blockage of an pulmonary artery, artery in the lungs by a substance that has moved from elsewhere in the body through the bloodstream (embolism). Symptoms of a PE may include dyspnea, shortness of breath, chest pain ...

. It may be used to prevent recurrent blood clot formation from atrial fibrillation, thrombotic stroke, and transient ischemic attacks. Coumarins have shown some evidence of biological activity and have limited approval for few medical uses as pharmaceuticals, such as in the treatment of lymphedema. Both coumarin and 1,3-indandione derivatives produce a uricosuric effect, presumably by interfering with the renal tubular reabsorption of urate.

Laser dyes

Coumarin dyes are extensively used as gain media in blue-green tunable organic dye lasers. Among the various coumarin

laser dye file:Coherent 899 dye laser.jpg, Close-up of a table-top dye laser using Rhodamine 6G as active medium. file:rhodamine 6G.svg, Molecular structure of Rhodamine 6G, perhaps the best known laser dye. A Laser dye is a dye used as laser medium in a dy ...

s are coumarins 480, 490, 504, 521, 504T, and 521T. Coumarin tetramethyl laser dyes offer wide tunability and high laser gain, and they are also used as active medium in coherent OLED emitters. and as a sensitizer in older photovoltaic technologies.

References

{{reflist Coumarins Phenylpropanoids