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Benzopyrones, coumarine· cumarines, kumarine
Empirical formula: C9H60 2 (= 1,2-benzopyrone)
Substance type: benzopyrone
Coumarin (= chromen-2-on, kumarin, 2H-1benzopyran-
2-on, o-cumar[in] acid lactone),
which has a scent like that of vanilla, crystallizes
into colorless prisms and is easily soluble in
alcohol, ether, and essential oils. Pure coumarin is
exuded from what are known as tonka beans, and
for this reason it is also called tonka bean camphor.
Coumarin is biosynthesized by the hydroxylation
of cinnamic acid or coumarin glycoside. Even
plants that do not actually contain any coumarin often produce it when they wilt (giving off the
smell of hay) or dry (e.g., Anthoxanthum
odoratum, Galium odoratum, Sida acuta).
Coumarins in Psychoactive Plants
(from Gray and Waterman1978; Rompp 1995*; Shoeb et ai. 1973; supplemented)
Coumarins (e.g., benzofuran) have been found in the following plants with demonstrated or
Umbelliferone, aesculine, and furocoumarin
are all coumarin derivatives. More than six
hundred natural coumarins are now known.
About two hundred coumarins occur in the
Family Rutaceae (including the genera Zanthoxylum,
Evodia, Ruta, Thamnosma, Dictamnus, Eriostemon,
Citrus, and Aegle), where they appear to
have great chemotaxonomic importance (Gray and
Waterman 1978; Tatum and Berry 1979).
Coumarins occur in some plants that are used
for psychoactive purposes (see scopoletin). Coumarin
is the substance responsible for the specific
taste of woodruff punch, and it is also present in
fahan tea (Angraecum fragrans Du Petit-Thouars),
which Bibra (1855*) described as psychoactive.
Fahan was once used as a substitute for green tea
(Camellia sinensis) and was mixed with tobacco
(Nicotiana tabacum) and rolled into cigars
(Frerichs et al. 1938, 1234*).
High dosages of pure coumarin can cause
headaches, dizziness, lethargyA lack of energy and enthusiasm., stupor, and even
respiratory paralysis (Roth et al. 1994, 796*).
Coumarin is said to be toxic to the liver and for
this reason was banned as a component or
ingredient in food. However, the toxicity is very
doubtful, and the alleged carcinogenic effects arealso questionable (Marles et al. 1987).
|Commercial Forms and Regulations
In the United States, coumarin has been banned as
a food additive since 1954. It has been placed in Class 3 of the Swiss Poison List. In Germany,
drinking brandies (380/0 alcohol) are allowed to
contain a maximum of 10 mg of coumarin per
liter (Roth et al. 1994,402*).
See also the entries for scopoletin.
Gray, Alexander 1., and Peter Waterman. 1978.
Coumarins in the Rutaceae. Phytochemistry
17:845-64. (Contains a rich bibliography.)
Marles, R. J., C. M. Compadre, and N. R. Farnsworth.
1987. Coumarin in vanilla extracts: Its detection
and significance. Economic Botany 41 :41-47.
Mendez, R. D. H., J. Murray, and S. A. Brown. 1982.
The natural coumarins. Chichester, U.K.: John
Reisch, J., et al. 1968. Dber weitere C3-substituierte
Cumarin-Derivate aus Ruta graveolens:
Daphnoretin und Daphnoretin-methyHither.
Planta Medica 15:372-76.
---. 1969. Dber die Cumarine der Wurzel von
Ruta graveolens. Planta Medica 17:116-19.
Shoeb, Aboo, Rhandhir S. Kapil, and Satya P. PopIi.
1973. Coumarins and alkaloids of Aegle
marmelos. Phytochemistry 12:2071-72.
Tatum, James H., and Robert E. Berry. 1979.
Coumarins and psoralkens in grapefruit peel oil.Phytochemistry 18:500-502.