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Revision as of 18:28, 13 January 2013

Other Names

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

purported psychoactivity:

Aegle marmelos Corr. coumarin
Anthoxanthutn odoratumL.(sweetvernal grass) coumarin
Dipteryx (Coumarouna) odorata (AubI.) Willd. coumarin
Dipteryxoppositifolia (Aubl.) .Willd. (tonka bean) coumarin
Evodia spp. (cf. Evodia bonwickii) coumarin
Galiumodoratum(L.}Scop.(woodruff) [syn. Asperula odorata 1.] coumarin
Hierochloe australis (1.) P. Beauv. (buffalo grass; vodka additive) coumarin
Flierochloe odorata (L.) P. Beauv. (sweet grass, vanilla grass; cf. incense) unidentified
Justicia pectoralis coumarin and others
Laval1dula angustifolia Mill. [syn. Lavandula officinalis Chaix] (c£ essential oils) coumarin and others
Melilotus officinalis (1.) Pall. various
Melilotus spp. (sweet clover) furanocoumarins
Petroselinum crispum rutin, gravolenic acid
Rutagraveolens 1. (cf. haoma, soma) coumarin
Sida acuta coumarin
Sidaspp. various
Tagetes spp. various
Thamnosma montana  
For plants containing the coumarin derivative scopoletin, see scopoletin.  

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 are

also 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*).

Literature

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

Wiley.

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.

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