Coumarin

(Redirected from Coumarine)
Jump to navigation Jump to search

Template:Chembox new

WikiDoc Resources for Coumarin

Articles

Most recent articles on Coumarin

Most cited articles on Coumarin

Review articles on Coumarin

Articles on Coumarin in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Coumarin

Images of Coumarin

Photos of Coumarin

Podcasts & MP3s on Coumarin

Videos on Coumarin

Evidence Based Medicine

Cochrane Collaboration on Coumarin

Bandolier on Coumarin

TRIP on Coumarin

Clinical Trials

Ongoing Trials on Coumarin at Clinical Trials.gov

Trial results on Coumarin

Clinical Trials on Coumarin at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Coumarin

NICE Guidance on Coumarin

NHS PRODIGY Guidance

FDA on Coumarin

CDC on Coumarin

Books

Books on Coumarin

News

Coumarin in the news

Be alerted to news on Coumarin

News trends on Coumarin

Commentary

Blogs on Coumarin

Definitions

Definitions of Coumarin

Patient Resources / Community

Patient resources on Coumarin

Discussion groups on Coumarin

Patient Handouts on Coumarin

Directions to Hospitals Treating Coumarin

Risk calculators and risk factors for Coumarin

Healthcare Provider Resources

Symptoms of Coumarin

Causes & Risk Factors for Coumarin

Diagnostic studies for Coumarin

Treatment of Coumarin

Continuing Medical Education (CME)

CME Programs on Coumarin

International

Coumarin en Espanol

Coumarin en Francais

Business

Coumarin in the Marketplace

Patents on Coumarin

Experimental / Informatics

List of terms related to Coumarin

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


Coumarin is a chemical compound; a toxin found in many plants, notably in high concentration in the tonka bean, woodruff, and bison grass. It has a sweet scent, readily recognised as the scent of newly-mown hay. It has clinical value as the precursor for several anticoagulants, notably warfarin. It is also 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" [2]. 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 [3][4], but some natural additives containing coumarin (such as sweet woodruff) are allowed "in alcoholic beverages only" (21 CFR 172.510 [5]). 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.[1]

Coumarin should be avoided by people with perfume allergy[2]. Flexitral (Chantilly, VA) has developed an allergen replacement product called Coumane(TM), GRAS. [3].

Compounds

Compounds within the coumarin family include:

Several of the above compounds are used as rodenticides.

References

  1. http://www.npr.org/templates/story/story.php?storyId=6672644
  2. Survey and health assessment of chemical substances in massage oils
  3. http://www.femaflavor.org/
  4. International Programme on Chemical Safety. ) "Brodifacoum (pesticide data sheet)" Check |url= value (help). Retrieved 2006-12-14.
  5. 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&ndash, 82.
  6. International Programme on Chemical Safety. "Bromadiolone (pesticide data sheet)". Retrieved 2006-12-14.
  7. Compendium of Pesticide Common Names. "Coumafuryl data sheet". Retrieved 2007-08-17.
  8. International Programme on Chemical Safety. "Difenacoum (health and safety guide)". Retrieved 2006-12-14.

External links


bg:Кумарин da:Kumarin de:Cumarin it:Cumarina nl:Coumarine sv:Kumarin

Template:Jb1 Template:WH Template:WS