Eugenol

Chembox new
Name = Eugenol
ImageFile = Eugenol acsv.svg
ImageName = Eugenol
ImageFile1 = Eugenol-spaceFill.png ImageSize1 = 200px
ImageName1 = Eugenol 3D
IUPACName = 4-Allyl-2-methoxyphenol
OtherNames=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
Section1 = Chembox Identifiers
CASNo = 97-53-0
SMILES = Oc1ccc(cc1OC)CC=C
Section2 = Chembox Properties
MolarMass = 164.20 g/mol
MeltingPtC = -9
BoilingPtC = 256
Density = 1.06 g/cm³
Section7 = Chembox Hazards
FlashPt = 104 °C

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, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma.

The name comes from a scientific name for the 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%

Modern uses

Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. [cite journal|author=Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS. |title=Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases |journal=Drug Dev Ind Pharm. |date=2004 Feb |volume=30 |issue=2 |pages=195–203|pmid=15089054 |doi=10.1081/DDC-120028715] 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, such as propanidid and G.29.505, there were unacceptable consequences in certain people. [cite journal |url=http://bja.oxfordjournals.org/cgi/content/abstract/34/6/379 |title=A clinical study of intravenous anaesthesia with a eugenol derivative, G.29.505 |journal=British Journal of Anaesthesia, |date=June 1962 |volume=34 |pages=379–385 |author=Right DA, Payne JP |pmid= 14008420 |format=abstract |doi=10.1093/bja/34.6.379] Clove oil is growing in popularity as an anaesthetic for use on aquarium fish.

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. [cite journal |url=http://www.springerlink.com/content/kv52574k74438848/ |author=Schiestl FP, Roubik DW |date=2003 Jan |title=Odor Compound Detection in Male Euglossine Bees |journal=Journal of Chemical Ecology |volume=29 |issue=1 |pages=253–257 |pmid=12647866 |doi=10.1023/A:1021932131526]

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. [ [http://www2.mst.dk/udgiv/publications/2006/87-7052-278-2/html/kap07_eng.htm Survey and health assessment of chemical substances in massage oils] ]

References

External links

* [http://scienceblogs.com/moleculeoftheday/2006/10/eugenol_mmm_dentist.php#commentsArea Eugenol entry on the "Molecule of the Day" blog]