Eugenol

Eugenol
IUPAC name	4-Allyl-2-methoxyphenol
Other names	2-Methoxy-4-(2-propenyl)phenol Eugenic acid Caryophyllic acid 1-Allyl-3-methoxy-4-hydroxybenzene Allylguaiacol 2-Methoxy-4-allylphenol 4-Allylcatechol-2-methyl ether 2-methoxy-4-(2-propen-1-yl)phenol
Identifiers
CAS number	97-53-0 Y
SMILES	Oc1ccc(cc1OC)CC=C
Properties
Molar mass	164.20 g/mol
Density	1.06 g/cm3
Melting point	−9 °C, 264 K, 16 °F
Boiling point	256 °C, 529 K, 493 °F
Hazards
Flash point	104 °C
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Eugenol (C₁₀H₁₂O₂), is an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf.^{[citation needed]} It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma.

The name is derived from the scientific name for clove, Eugenia aromaticum or Eugenia caryophyllata. Eugenol is responsible for the aroma of cloves. It is the main component in the essential oil extracted from cloves, comprising 72-90% of the total.

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, eugenol forms a material 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, such as propanidid and G.29.505, there were unacceptable consequences in certain people.^[2] Clove oil is growing in popularity as an anaesthetic for use on aquarium fish as well as on wild fish when sampled for research and management purposes.

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

Eugenol is hepatotoxic.^[4][5]

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.^[6] A 2-year old boy nearly died after taking between 5 and 10 ml., according to a published 1993 report.^[7]

Eugenol should be avoided by people with perfume allergy.^{[8][clarification needed]} Eugenol may cause allergic contact dermatitis with the skin.^[9]

List of plants that contain the chemical

• Syzygium aromaticum (cloves)^[10][11][12]
• Cinnamon ^[11][13]
• Cinnamomum tamala ^{[14][clarification needed]}
• Myristica fragrans (nutmeg)^{[15][clarification needed]}
• Ocimum basilicum ^[16]
• Japanese star anise ^[17]

This section requires expansion.

See also

• [Signs and Symptoms of Eugenol Poisoning http://www.pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33197#Symptoms]
• Zinc oxide eugenol

References

External links

• [Toxicity Information for Eugenol | http://www.pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC33197#Toxicity]
• Eugenol entry on the Molecule of the Day blog