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Coumarins - Revision history
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2015-03-11T10:57:03Z
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GrimReaper
https://wiki.tripsit.me/index.php?title=Coumarins&diff=391&oldid=prev
205.56.181.196: Created page with " <table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0"> <tr> <td valign="top" width="50%"><strong>..."
2013-01-13T18:28:12Z
<p>Created page with " <table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0"> <tr> <td valign="top" width="50%"><strong>..."</p>
<p><b>New page</b></p><div><br />
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" width="100%" border="0" cellspacing="0" cellpadding="0"><br />
<br />
<tr><br />
<td valign="top" width="50%"><strong>Other Names</strong><br />
<br />
Benzopyrones, coumarine· cumarines, kumarine<br />
<br />
Empirical formula: C9H60 2 (= 1,2-benzopyrone)<br />
<br />
Substance type: benzopyrone<br />
<br />
Coumarin (= chromen-2-on, kumarin, 2H-1benzopyran-<br />
<br />
2-on, o-cumar[in] acid lactone),<br />
<br />
which has a scent like that of vanilla, crystallizes<br />
<br />
into colorless prisms and is easily soluble in<br />
<br />
alcohol, ether, and essential oils. Pure coumarin is<br />
<br />
exuded from what are known as tonka beans, and<br />
<br />
for this reason it is also called tonka bean camphor.<br />
<br />
Coumarin is biosynthesized by the hydroxylation<br />
<br />
of cinnamic acid or coumarin glycoside. Even<br />
<br />
plants that do not actually contain any coumarin often produce it when they wilt (giving off the<br />
<br />
smell of hay) or dry (e.g., Anthoxanthum<br />
<br />
odoratum, Galium odoratum, Sida acuta).<br />
<br />
<strong>Coumarins in Psychoactive Plants</strong><br />
<br />
(from Gray and Waterman1978; Rompp 1995*; Shoeb et ai. 1973; supplemented)<br />
<br />
Coumarins (e.g., benzofuran) have been found in the following plants with demonstrated or<br />
<br />
purported psychoactivity:<br />
<table style="font-family: Arial, Helvetica, sans-serif; font-size: 9pt;" border="0" cellspacing="0" cellpadding="0"><br />
<br />
<tr><br />
<td valign="top" width="319"><em>Aegle marmelos </em>Corr.</td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Anthoxanthutn odoratumL.(sweetvernal </em>grass)</td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Dipteryx (Coumarouna) odorata </em>(AubI.) Willd.</td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Dipteryxoppositifolia </em>(Aubl.) .Willd. (tonka bean)</td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Evodia </em>spp. (cf. <em>Evodia bonwickii)</em></td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Galiumodoratum(L.}Scop.(woodruff) </em>[syn. <em>Asperula odorata </em>1.]</td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Hierochloe australis </em>(1.) P. Beauv. (buffalo grass; vodka additive)</td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Flierochloe odorata </em>(L.) P. Beauv. (sweet grass, vanilla grass; cf. incense)</td><br />
<td valign="top" width="319">unidentified</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Justicia pectoralis</em></td><br />
<td valign="top" width="319">coumarin and others</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Laval1dula angustifolia </em>Mill. [syn. <em>Lavandula officinalis </em>Chaix] (c£ essential oils)</td><br />
<td valign="top" width="319">coumarin and others</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Melilotus officinalis </em>(1.) Pall.</td><br />
<td valign="top" width="319">various</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Melilotus </em>spp. (sweet clover)</td><br />
<td valign="top" width="319">furanocoumarins</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Petroselinum crispum</em></td><br />
<td valign="top" width="319">rutin, gravolenic<br />
<br />
acid</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Rutagraveolens </em>1. (cf. haoma, soma)</td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Sida acuta</em></td><br />
<td valign="top" width="319">coumarin</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Sidaspp.</em></td><br />
<td valign="top" width="319">various</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Tagetes </em>spp.</td><br />
<td valign="top" width="319">various</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319"><em>Thamnosma montana</em></td><br />
<td valign="top" width="319">&nbsp;</td><br />
</tr><br />
<tr><br />
<td valign="top" width="319">For plants containing the coumarin derivative scopoletin, see scopoletin.</td><br />
<td valign="top" width="319">&nbsp;</td><br />
</tr><br />
<br />
</table><br />
Umbelliferone, aesculine, and furocoumarin<br />
<br />
are all coumarin derivatives. More than six<br />
<br />
hundred natural coumarins are now known.<br />
<br />
About two hundred coumarins occur in the<br />
<br />
Family Rutaceae (including the genera Zanthoxylum,<br />
<br />
Evodia, Ruta, Thamnosma, Dictamnus, Eriostemon,<br />
<br />
Citrus, and Aegle), where they appear to<br />
<br />
have great chemotaxonomic importance (Gray and<br />
<br />
Waterman 1978; Tatum and Berry 1979).<br />
<br />
Coumarins occur in some plants that are used<br />
<br />
for psychoactive purposes (see scopoletin). Coumarin<br />
<br />
is the substance responsible for the specific<br />
<br />
taste of woodruff punch, and it is also present in<br />
<br />
fahan tea (Angraecum fragrans Du Petit-Thouars),<br />
<br />
which Bibra (1855*) described as psychoactive.<br />
<br />
Fahan was once used as a substitute for green tea<br />
<br />
(Camellia sinensis) and was mixed with tobacco<br />
<br />
(Nicotiana tabacum) and rolled into cigars<br />
<br />
(Frerichs et al. 1938, 1234*).<br />
<br />
High dosages of pure coumarin can cause<br />
<br />
headaches, dizziness, lethargy, stupor, and even<br />
<br />
respiratory paralysis (Roth et al. 1994, 796*).<br />
<br />
Coumarin is said to be toxic to the liver and for<br />
<br />
this reason was banned as a component or<br />
<br />
ingredient in food. However, the toxicity is very<br />
<br />
doubtful, and the alleged carcinogenic effects are<br />
<br />
also questionable (Marles et al. 1987).</td><br />
<td valign="top" width="53%"><strong>Commercial Forms and Regulations</strong><br />
<br />
In the United States, coumarin has been banned as<br />
<br />
a food additive since 1954. It has been placed in Class 3 of the Swiss Poison List. In Germany,<br />
<br />
drinking brandies (380/0 alcohol) are allowed to<br />
<br />
contain a maximum of 10 mg of coumarin per<br />
<br />
liter (Roth et al. 1994,402*).<br />
<br />
<strong>Literature</strong><br />
<br />
See also the entries for scopoletin.<br />
<br />
Gray, Alexander 1., and Peter Waterman. 1978.<br />
<br />
Coumarins in the Rutaceae. Phytochemistry<br />
<br />
17:845-64. (Contains a rich bibliography.)<br />
<br />
Marles, R. J., C. M. Compadre, and N. R. Farnsworth.<br />
<br />
1987. Coumarin in vanilla extracts: Its detection<br />
<br />
and significance. Economic Botany 41 :41-47.<br />
<br />
Mendez, R. D. H., J. Murray, and S. A. Brown. 1982.<br />
<br />
The natural coumarins. Chichester, U.K.: John<br />
<br />
Wiley.<br />
<br />
Reisch, J., et al. 1968. Dber weitere C3-substituierte<br />
<br />
Cumarin-Derivate aus Ruta graveolens:<br />
<br />
Daphnoretin und Daphnoretin-methyHither.<br />
<br />
Planta Medica 15:372-76.<br />
<br />
---. 1969. Dber die Cumarine der Wurzel von<br />
<br />
Ruta graveolens. Planta Medica 17:116-19.<br />
<br />
Shoeb, Aboo, Rhandhir S. Kapil, and Satya P. PopIi.<br />
<br />
1973. Coumarins and alkaloids of Aegle<br />
<br />
marmelos. Phytochemistry 12:2071-72.<br />
<br />
Tatum, James H., and Robert E. Berry. 1979.<br />
<br />
Coumarins and psoralkens in grapefruit peel oil.<br />
<br />
Phytochemistry 18:500-502.</td><br />
</tr><br />
<br />
</table></div>
205.56.181.196