Eugenol

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Eugenol
200px
IUPAC name Eugenol
Other names 2-Methoxy-4-(2-propenyl)phenol
Allylguaiacol
4-Allyl-2-methoxyphenol
Eugenic acid
Caryophyllic acid
1-Allyl-3-methoxy-4-hydroxybenzene
5-Allylguaiacol
2-Methoxy-4-allylphenol
4-Allylguaiacol
4-allylcatechol-2-methyl ether
4-allyl-1-hydroxy-2-methoxybenzene
1-hydroxy-2-methoxy- 4-prop-2-enylbenzene
1,3,4-eugenol
1-hydroxy-2-methoxy-4-allylbenzene
4-hydroxy-3-methoxyallylbenzene
2-methoxy -1-hydroxy-4-allylbenzene
1-allyl-4-hydroxy-3-methoxybenzene
1-hydroxy-4-allyl-2-methoxybenzene
1-hydroxy-2-methoxy-4-propenylbenzene
2-methoxy-4-(2-propen-1-yl)phenol
Identifiers
CAS number 97-53-0
Properties
Molar mass 164.20 g/mol
Density 1.06 g/cm3
Melting point

-9 °C

Boiling point

256 °C

Hazards
Flash point 104 °C<
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Eugenol (C10H12O2), is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma.

Modern uses

Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic.[1] It is a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin.

When mixed with zinc oxide, zinc oxide eugenol forms which has restorative and prosthodontic applications in dentistry.

Eugenol derivatives or methoxyphenol derivatives in wider classification are used in perfumery and flavoring. They are used in formulating insect attractants and UV absorbers, analgesics, biocides and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Although attempts have been made to develop eugenol derivatives for intravenous injection, the toxicity of propanidid and G.29.505[2] in human patients was not acceptable. Clove oil is growing in popularity as an anaesthetic for use on aquarium fish.

Eugenol is also used clandestinely for the synthesis of phenethylamines (like MDMA).

It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.[3]

Toxicity

Overdose is possible, causing a wide range of symptoms from blood in the patient's urine, to convulsions, diarrhea, nausea, unconsciousness, dizziness, or rapid heartbeat. Eugenol may cause allergic contact dermatitis with the skin.

Health & Safety information

Eugenol should be avoided by people with perfume allergy[4].

References

  1. PMID 15089054
  2. D. A. RIGHT and J. P. PAYNE. "A CLINICAL STUDY OF INTRAVENOUS ANAESTHESIA WITH A EUGENOL DERIVATIVE, G.29.505". British Journal of Anaesthesia, 1962, Vol. 34, No. 6 379-385. 
  3. [1]Schiestl, F.P. & Roubik, D.W. (2004) Odor Compound Detection in Male Euglossine Bees. Journal of Chemical Ecology 29: 253-257.
  4. Survey and health assessment of chemical substances in massage oils

External links

da:Eugenol

de:Eugenolit:Eugenolo nl:Eugenolth:ยูเจนอล


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