- 4 -allyl-2 -methoxyphenol
- 4 -Prop -2-enyl - 2-methoxyphenol
- 4- methyl -2- Allylbrenzcatechin
- 5 - Allylguajacol
A colorless, oily, intense smells of cloves liquid
1.07 g · cm -3 ( 20 ° C)
-9 ° C.
253 ° C
< 0.1 hPa ( 20 ° C)
Poorly in water ( 2.46 g · l-1 at 25 ° C)
1930 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
Eugenol is a phenylpropanoid with an intense smell of cloves.
Eugenol occurs naturally in clove oil ( 70-95 %), in allspice and Pimento (60-90 % ) in bay oil (50-60%) and cinnamon oils ( cinnamon bark oil 5-10 %, cinnamon leaf oil over 90 %) before. In addition, it is found in bay leaves, basil, banana, cherry and nutmeg.
Production and representation
Eugenol is obtained by extraction of clove oil with five percent potassium hydroxide solution.
With potassium permanganate or ozone is eugenol (1) (over isoeugenol, 2) oxidized to vanillin (3). In the air it will gradually brown and gummy.
Eugenol is used in large quantities in the perfume industry for spicy notes, especially for carnations types and oriental scent directions. Eugenol is obtained in addition to the papermaking lignosulfonate, a main starting material ( reactant) for production of synthetic vanillin.
In dentistry, eugenol is used as an analgesic (only superficially ), antibacterial and anti-inflammatory agent. It is marketed under the trade name Ledermix m eugenol cement solution ® used for the prophylaxis of pulpitis, for the treatment of acute pulpitis or acute periodontitis. Also in temporary cements and filling materials (zinc oxide -eugenol cement) together with Eugenolether, Eugenolbenzoat, Eugenolcinnamat, eugenol eugenol comes to application.
Biological significance and activity
A phytochemical database lists 68 areas of biological activity of eugenol. In the Zoological / microbiological area, it has an antibacterial effect ( and Others against salmonella and staphylococcus ); antifungal ( against Candida ); against nematodes and trichomoniasis; acaricidally (ie against mites and ticks ), insecticidal and insektifugal, also larvicidal; apifugal ( bees expelling ); and against termites. Some insect species are attracted by eugenol ( Euglossa, Maladera ).
In humans, it has analgesic and anti-inflammatory. In the laboratory to inhibit the tumor necrosis factor and thromboxane enzymes, COX-1, COX-2 and cytochrome P450. Many other individual effects were noted. Clinical trials also are unknown. In the metabolism of eugenol mainly arise phase II conjugates with glucuronic acid, glutathione, sulfate and. In the radical transformation the harmful quinone can occur.
Furthermore, eugenol can be used as an anesthetic for fish.
Eugenol is cytotoxic and genotoxic; the genotoxic effects depend on activation by the enzyme P450. It is both an antioxidant and a pro-oxidant; based on the latter probably his ( mucus ) skin-irritating, allergy -promoting effect.