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07-SEPTEMBER-2008 03:17:44 - Coumarin Coumarin IUPAC name 2-chromenone Identifiers CAS number 91-64-5 PubChem 323 SMILES C1=CC=C2C=C1C=CC=OO2 Properties Molecular formula C9H6O2 Molar mass 146.143 Density 0.935 g/cm³ 20 °C Melting point 71 °C Boiling point 301 °C Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Coumarin is a chemical compound benzopyrone; a toxin found in many plants, notably in high concentration in the tonka bean, vanilla grass, 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. Contents 1 Synthesis 2 Biological Function 3 Derivatives 4 Medical Use 5 Toxicity and use in Foods, Beverages, Tobacco, and Cosmetics 6 Compounds 7 References 8 External links 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. Image:Cumarinsynthese.png The Pechmann condensation provides another synthesis of coumarin and its derivatives. Biological Function Coumarin has appetite suppressing properties, suggesting its widespread occurrence in plants, especially grasses, is because of its effect of reducing the impact of grazing animals. 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. Medical Use Coumarin has been used in the treatment of lymphedema.1 Toxicity and use in Foods, Beverages, Tobacco, and Cosmetics Coumarin 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. The German Federal Institute for Risk Assessment has established a tolerable daily intake of 0.1 mg coumarin per kg body weight, but also advises that, if this level is exceeded for a short time only, there is no threat to health.2 For example, a person weighing 135 lbs or about 61 kg would have a TDI of approximately 6.1 mg of coumarin. European health agencies have warned against consuming high amounts of cassia bark, one of the four species of cinnamon, because of its coumarin content.3. According to the German Federal Institute for Risk Assessment, 1 kg of cassia cinnamon powder contains approximately 2100 to 4400 mg of coumarin.4 Powdered Cassia Cinnamon weighs 0.56 g/cc5; therefore, 1 kg of Cassia Cinnamon powder is equal to 362.29 teaspoons 1000 g divided by 0.56 g/cc multiplied by 0.20288 tsp/cc. This means 1 teaspoon of cinnamon powder contains 5.8 to 12.1 mg of coumarin, which may be above the Tolerable Daily Intake for smaller individuals.6 However, it is important to note that the German Federal Institute for Risk Assessment only cautions against high daily intakes of foods containing coumarin. Coumarin is often found in tobacco products and artificial vanilla substitutes, despite having been banned as a food additive in numerous countries since the mid-20th century. 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 1. 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.citation needed 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 23, but some natural additives containing coumarin such as sweet woodruff are allowed in alcoholic beverages only 21 CFR 172.510 4. In Europe, such beverages are very popular, for example Maiwein white wine with woodruff and Å»ubrówka vodka flavored with bison grass. Coumarin should be avoided by people with perfume allergy.7 Flexitral Chantilly, VA has developed an allergen replacement product called CoumaneTM, GRAS.8 Compounds Compounds derived from coumarin are also called coumarins. Compounds within this coumarin family include: brodifacoum,910 bromadiolone,11 coumafuryl,12 and difenacoum.13 Ensaculin warfarin phenprocoumon Marcoumar Several of the above compounds are used as anticoagulant drugs and/or as rodenticides. References ^ Pharmacogenomics: Its Role in Re-establishing Coumarin as Treatment for Lymphedema June 1, 2005. Lymphatic Research and Biology 3 2: 81-86. doi:10.1089/lrb.2005.3.81. ^ Frequently Asked Questions about coumarin in cinnamon and other foods 30 October 2006. ^ NPR: German Christmas Cookies Pose Health Danger ^ High daily intakes of cinnamon: Health risk cannot be ruled out. BfR Health Assessment No. 044/2006, 18 August 2006 ^ Engineering Resources - Bulk Density Chart ^ High daily intakes of cinnamon: Health risk cannot be ruled out. BfR Health Assessment No. 044/2006, 18 August 2006 ^ Survey and health assessment of chemical substances in massage oils ^ FEMA ^ International Programme on Chemical Safety. Brodifacoum pesticide data sheet. Retrieved on 2006-12-14. ^ Laposata M, Van Cott EM, Lev MH. 2007. Case 1-2007-A 40-Year-Old Woman with Epistaxis, Hematemesis, and Altered Mental Status 356 2: 174-82. ^ International Programme on Chemical Safety. Bromadiolone pesticide data sheet. Retrieved on 2006-12-14. ^ Compendium of Pesticide Common Names. Coumafuryl data sheet. Retrieved on 2007-08-17. ^ International Programme on Chemical Safety. Difenacoum health and safety guide. Retrieved on 2006-12-14. External links More info about coumarin Coumarin in tobacco More info about CoumaneTM Coumarin as an ingredient of perfume. 5 v d e Types of Phenylpropanoids Phenylpropanoids Cinnamic acids Cinnamaldehydes Monolignols Coumarins Flavonoids Stilbenoids Furanocoumarin Lignans Lignins Suberins Retrieved from http://en..org/wiki/Coumarin Categories: Lactones | Phenylpropanoids | Oxygen heterocycles | Fluorescent dyes | Fuel dyes | Laser gain mediaHidden categories: All articles with statements | Articles with statements since February 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки Dansk Deutsch Español Français Italiano Nederlands 日本語 Polski Română РуÑ?Ñ?кий Suomi Svenska This page was last modified on 27 August 2008, at 10:28
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