Coumarin (/ ˈ k uː m ər ɪ n /) or 2H-chromenone is an aromatic organic chemical compound with formula C 9 H 6 O blogger.com molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone Weigel Health Center is located on Academic Drive, (Parking Lot R6) next to Chase Hall (University Police). Click here for the Campus Map.. Weigel Health Center provides health and wellness services for all registered students, including part-time, full-time, commuter, residential, Graduate, and Undergraduate students.. Parents, Guardians - According to HIPAA regulations, Weigel Wellness Increasing cultivation of tobacco required more land (since tobacco wore out the soil in three or four years) and clearing forest areas to make land fit for planting. Expanding English settlements meant more encroachment on Native American lands and somewhat greater contact with Native Americans. It also left settlers more vulnerable to attack
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It can be placed tobacco essay the benzopyrone tobacco essay class and considered as a lactone. Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste. By inhibiting synthesis of vitamin Ka related compound is used as the prescription drug warfarin — an anticoagulant — to inhibit formation of blood clotsdeep vein thrombosisand pulmonary embolism.
Coumarin is derived from coumarouthe French word for the tonka bean. The word tonka for the tonka bean is taken from the Galibi Carib tongue spoken by natives of French Guiana one source for the plant ; it also appears in Old Tupianother language of the same region, as the name of the tree. The old genus name, tobacco essay, Coumarounawas formed from another Tupi name for tree, tobacco essay, kumarú.
Coumarin was first isolated from tonka beans in by A. Vogel of Munich, who initially mistook it for benzoic acid. Also inNicholas Jean Baptiste Gaston Guibourt — of France independently isolated coumarin, but he realized that it was not benzoic acid.
Inthe French pharmacist A, tobacco essay. Guillemette proved that Vogel and Guibourt had isolated the same substance. Coumarin has been an integral part of the fougère genre of perfume since it was first used in Houbigant's Fougère Royale in Coumarin can be prepared by a number of name reactionswith the Perkin reaction between salicylaldehyde and acetic anhydride being a popular example. The Pechmann condensation provides another route to coumarin and its derivatives, as does the Kostanecki acylationwhich can also be used tobacco essay produce chromones.
Coumarin is found naturally in many plantsnotably in high concentration in the tonka bean Dipteryx odorata. It also occurs in vanilla grass Anthoxanthum odoratumsweet woodruff Galium odoratumsweet grass Hierochloe odorata and sweet-clover genus Melilotuswhich are named for the sweet i. Other plants with substantial coumarin content include cassia cinnamon Cinnamomum cassianot to be confused with true cinnamon Cinnamomum verumwhich contains little coumarin, [11] deertongue Carphephorus odoratissimus[12] tilo Justicia tobacco essay[13] [14] mullein genus Verbascumand in many cherry blossom tree varieties of the genus Prunus.
Coumarin is found naturally also in many edible plants such as strawberriesblack currants tobacco essay, apricotsand cherries. Coumarin has appetite-suppressing properties, tobacco essay, which may discourage animals from eating plants that contain it, tobacco essay. Though the compound has a pleasant sweet odor, it has a bitter taste, and animals tend to avoid it. The biosynthesis of coumarin in plants is via hydroxylationglycolysisand cyclization of cinnamic acid.
Coumarin and its derivatives are all considered phenylpropanoids. Some naturally occurring coumarin derivatives include umbelliferone 7-hydroxycoumarinaesculetin 6,7-dihydroxycoumarinherniarin 7-methoxycoumarinpsoralen and imperatorin, tobacco essay. Coumarin pyrazole hybrids have been synthesized from hydrazones, carbazones and thiocarbazones via Vilsmeier Haack formylation reaction, tobacco essay.
Coumarin is transformed into the natural anticoagulant dicoumarol by a number of species of fungi. Dicoumarol was responsible for the bleeding tobacco essay known historically as " sweet clover disease" in cattle eating moldy sweet clover silage.
Warfarin — a coumarin — with brand nameCoumadinis a prescription drug used as an anticoagulant to inhibit formation of blood clots, and so is a therapy for deep vein thrombosis and pulmonary embolism. 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.
Coumarin is used in the pharmaceutical industry as a precursor reagent in the synthesis of a number of synthetic anticoagulant pharmaceuticals similar to dicoumarol. Some of the 4-hydroxycoumarin anticoagulant class of chemicals are designed to have high potency and long residence times in the body, and these are used specifically as rodenticides "rat poison".
Coumarin dyes are extensively used as gain media in blue-green tunable organic dye lasers. Coumarin is often found in artificial vanilla substitutes, despite having been banned as a food additive in numerous countries since the midth century. It is still used as a legal flavorant in soaps, rubber products, and the tobacco industry, [1] particularly for sweet pipe tobacco and certain alcoholic drinks.
Though it is only somewhat dangerous to humans, coumarin is hepatotoxic in rats, but less so in mice. Rodents metabolize it mostly to 3,4-coumarin epoxidea toxic, unstable compound that on further differential metabolism may cause liver cancer in tobacco essay and lung tumors in mice. The German Federal Institute for Risk Assessment has established a tolerable daily intake TDI of tobacco essay. European health agencies have warned against consuming high amounts of cassia bark, one of the four main species of cinnamonbecause of its coumarin content.
One teaspoon of cassia cinnamon powder therefore contains 5, tobacco essay. Its report [43] specifically states that Ceylon cinnamon Cinnamomum verum contains "hardly any" coumarin. Coumarin was banned as a food additive in the United States inlargely because of the hepatotoxicity results in rodents. Coumarin is subject to restrictions on its use in perfumery, [50] as some people may become sensitized to it, however the evidence that coumarin can cause an allergic reaction in humans is disputed.
Minor neurological dysfunction was found in children exposed to the anticoagulants tobacco essay or phenprocoumon during pregnancy. A group of children were tested at ages 7—15 years to determine subtle neurological effects from anticoagulant exposure. Results showed a dose—response relationship between anticoagulant exposure and minor neurological dysfunction.
Overall, a 1. Wigand later stated that coumarin itself is dangerous, pointing out that the FDA had banned its addition to human food in Clear cinnamon-flavored alcoholic beverages generally test negative for coumarin, tobacco essay if whole cassia bark is used to make mulled winethen coumarin shows up at significant levels. From Wikipedia, the free encyclopedia. Aromatic chemical compound. This article is about the simple chemical coumarin.
For the anticoagulants and rodenticides called "coumarins" or "coumadins", see 4-hydroxycoumarins, tobacco essay. It has been suggested that this article be split into articles titled Coumarin and Coumarins. Discuss October CAS Number. Interactive image. Beilstein Reference. CHEBI Y. ChEMBL Y. DB Y. Gmelin Reference. D Y. PubChem CID. A4VZ22K1WT Y, tobacco essay. CompTox Dashboard EPA. Chemical formula. Solubility in water. Magnetic susceptibility χ. Crystal structure.
GHS hazard statements. GHS precautionary statements. LD 50 median dose. Except where otherwise noted, data are given for materials in their standard state at 25 °C [77 °F], tobacco essay, kPa. Chemical compound. Main article: 4-Hydroxycoumarins. PubChem, National Library of Medicine, Tobacco essay National Tobacco essay of Health. Retrieved 13 April Retrieved 24 December Annalen der Physik in German. Bibcode : AnP doi : Journal de Pharmacie in French. Histoire Abrégée des Drogues Simples [ Abridged History of Simple Drugs ] in French.
Paris: L. Journal de Chimie Médicale, de Pharmacie et de Toxicologie. plus récemment, dans un essai de nomenclature chimique, lu à la section de Pharmacie de l'Académie royale de Médecine, tobacco essay, il l'a désignée sous le nom de coumarine, tiré du nom du végétal coumarouna odorata more recently, in an essay on chemical nomenclature, [which was] read to the pharmacy section of the Royal Academy of Medicine, tobacco essay, he [Guibourt] designated it by the name "coumarine," derived from the name of the vegetable Coumarouna odorata Histoire Naturelle des Drogues Simples 6th ed.
Paris: J. Baillière et fils. la matière cristalline de la fève tonka matière que j'ai nommée coumarine the crystalline matter of the tonka bean matter that Tobacco essay named coumarine Journal de Pharmacie. Journal of the Chemical Society. Retrieved 13 November Dhammika; Zhao, Jianping; Khan, Ikhlas A.
Journal of Agricultural and Food Chemistry. PMID Leung's Encyclopedia of Common Natural Ingredients Used in Food, tobacco essay, Drugs, and Cosmetics PDF. ISBN
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, time: 5:21Coumarin - Wikipedia
Coumarin (/ ˈ k uː m ər ɪ n /) or 2H-chromenone is an aromatic organic chemical compound with formula C 9 H 6 O blogger.com molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone Weigel Health Center is located on Academic Drive, (Parking Lot R6) next to Chase Hall (University Police). Click here for the Campus Map.. Weigel Health Center provides health and wellness services for all registered students, including part-time, full-time, commuter, residential, Graduate, and Undergraduate students.. Parents, Guardians - According to HIPAA regulations, Weigel Wellness Increasing cultivation of tobacco required more land (since tobacco wore out the soil in three or four years) and clearing forest areas to make land fit for planting. Expanding English settlements meant more encroachment on Native American lands and somewhat greater contact with Native Americans. It also left settlers more vulnerable to attack
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