AskDefine | Define coumarin

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English

Noun

  1. the bicyclic aromatic compound 1,2-benzopyrone or any of its derivatives

Extensive Definition

Coumarin is a chemical compound (benzopyrone); a toxin found in many plants, notably in high concentration in the tonka bean, woodruff, mullein, and bison grass. It has a sweet scent, readily recognised as the scent of newly-mown hay, and has been used in perfumes since 1882. It has clinical medical value as the precursor for several anticoagulants, notably warfarin, and is used as a gain medium in some dye lasers.
The name comes from a French word, coumarou, for the tonka bean.

Synthesis

The biosynthesis of coumarin in plants is via hydroxylation, glycolysis and cyclization of cinnamic acid. Coumarin can be prepared in a laboratory in a Perkin reaction between salicylaldehyde and acetic anhydride.
The Pechmann condensation provides another synthesis of coumarin and its derivatives.

Derivatives

Some naturally occurring coumarin derivatives include umbelliferone (7-hydroxycoumarin), aesculetin (6,7-dihydroxycoumarin), herniarin (7-methoxycoumarin), psoralen and imperatorin. Coumarin and its derivatives are all considered phenylpropanoids.

Coumarin toxicity

Coumarin is often found in tobacco products and artificial vanilla substitutes, though it has been banned as a food additive in numerous countries since the mid-20th century because it is moderately toxic to the liver and kidneys, with an LD50 of 275 mg/kg - low compared to related compounds. Although only somewhat dangerous to humans, coumarin is a potent rodenticide: rats and other rodents largely metabolize it to 3,4-coumarin epoxide, a toxic compound that can cause internal hemorrhage and death. Humans largely metabolize it to 7-hydroxycoumarin, a compound of lower toxicity.
Coumarin was banned as a food additive in the United States in 1978. OSHA considers this compound to be only a lung-specific carcinogen, and "not classifiable as to its carcinogenicity to humans" http://www.osha.gov/dts/chemicalsampling/data/CH_229620.html. Coumarin was banned as an adulterant in cigarettes by tobacco companies in 1997, but due to the lack of reporting requirements to the US Department of Health and Human Services it was still being used as a flavoring additive in pipe tobacco. Coumarin is currently listed by the United States Food and Drug Administration (FDA) among "Substances Generally Prohibited From Direct Addition or Use as Human Food", according to 21 CFR 189.130 http://www.access.gpo.gov/nara/cfr/waisidx_06/21cfr189_06.htmlhttp://www.cfsan.fda.gov/~dms/eafus.html, but some natural additives containing coumarin (such as sweet woodruff) are allowed "in alcoholic beverages only" (21 CFR 172.510 http://www.access.gpo.gov/nara/cfr/waisidx_06/21cfr172_06.html). In Europe, such beverages are very popular, for example Maiwein (white wine with woodruff) and Żubrówka (vodka flavored with bison grass).
European health agencies have warned against consuming high amounts of cassia bark, one of the four species of cinnamon, because of its coumarin content.
Coumarin should be avoided by people with perfume allergy. Flexitral (Chantilly, VA) has developed an allergen replacement product called Coumane(TM), GRAS.

Compounds

Compounds derived from coumarin are also called "coumarins". Compounds within this coumarin family include:
Several of the above compounds are used as anticoagulant drugs and/or as rodenticides.

References

coumarin in Bulgarian: Кумарин
coumarin in Danish: Kumarin
coumarin in German: Cumarin
coumarin in Spanish: Cumarina
coumarin in French: Coumarine
coumarin in Italian: Cumarina
coumarin in Dutch: Coumarine
coumarin in Japanese: クマリン
coumarin in Polish: Kumaryna
coumarin in Romanian: Cumarină
coumarin in Russian: Кумарин
coumarin in Finnish: Kumariini
coumarin in Swedish: Kumarin
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