Chemical Properties
colourless to faintly yellow liquid with a strong odour of cloves
Uses
analgesic (topical), antiseptic, antifungal
Uses
blood volume expander
Uses
Eugenol is a dental compound which shows cytotoxicity to human oral squamous cell carcinoma and oral cells. When glucosylated, this compound exhibits anti-inflammatory activity.
Definition
ChEBI: A phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group.
General Description
Clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste.
Reactivity Profile
EUGENOL is incompatible with strong oxidizers. This includes ferric chloride and potassium permanganate. EUGENOL reacts with strong alkalis. EUGENOL is incompatible with iron and zinc.
Air & Water Reactions
Darkens and thickens on exposure to air. Also darkens with age. EUGENOL(97-53-0) may decompose on exposure to light. Insoluble in water.
Hazard
Questionable carcinogen.
Fire Hazard
This chemical is combustible.
Description
Sensitization to eugenol mainly occurs in those in
dental professions. Eugenol is contained in the "fragrance
mix".
Occurrence
Reported found as a constituent in several volatile oils: clove oil, laurel and cinnamon leaf oil. Smaller amounts
of eugenol are also present in the oil of camphor, Java citronella, California laurel and acacia flowers; remarkable amounts of eugenol
are found in Ocimum sanctum (70%) and Ocimum gratissimum (60%). Eugenol is also found in the oil from violet flowers (21%);
in some plants, eugenol probably occurs as glucoside. Reported found in apricot, citrus oils, raspberry, strawberry, tomato, anise,
cinnamon (leaf, bark and roots), clove bud and stem, nutmeg, mace, pepper, smoked fish, beer, whiskey, grape wines, cocoa, mango,
tarragon, laurel, myrtle leaf, and pimento berry and leaf.
Aroma threshold values
Detection: 6 to 100 ppb
Anticancer Research
This compound was tested on a model of skin tumor induced by DMBA croton oilin Swiss mice. The eugenol affects the cellular proliferation by increasing apoptosiscellular death. There is evidence for a downregulation of c-myc, H-ras, and Bcl-2expression and an upregulation of p53, Bax, and active caspase-3 (Grondona et al.2014).
Clinical Use
4-Allyl-2-methoxyphenol is obtained primarily from cloveoil. It is a pale-yellow liquid with a strong aroma of clovesand a pungent taste. Eugenol is only slightly soluble in waterbut is miscible with alcohol and other organic solvents.Eugenol possesses both local anesthetic and antiseptic activityand can be directly applied on a piece of cotton to relievetoothaches. Eugenol is also used in mouthwashes because ofits antiseptic property and pleasant taste. The phenol coefficientof eugenol is 14.4.
Synthesis
The oil containing eugenol is treated with a 3% aqueous solution of NaOH; the nonacid components are extracted with
ether; the alkaline solution is acidified to isolate the phenols and subsequently is fractionally distilled under reduced pressure; to
avoid the formation of emulsions, a pretreatment of the oil with tartaric acid is preferred; eugenol is the starting material in one of the
syntheses for the preparation of vanillin.
Metabolism
No absorption of eugenol occurred within 2hr of application to the intact shaved skin of mice (Meyer & Meyer, 1959). Following ip injec tion of [14C]eugenol into rats, radioactivity was dis tributed in various organs and the presence of 14CO2 in the expired air indicated the demethylation of eugenol (Weinberg, Rabinowitz, Zanger & Gennaro, 1972). Over 70% of an oral dose of eugenol was excreted in the urine of rabbits (Schr?der & Vollmer, 1932).
Purification Methods
Fractional distillation of eugenol gives a pale yellow liquid which darkens and thickens on exposure to air. It should be stored under N2 at -20o. [Waterman & Priedster Recl Trav Chim Pays-Bas 48 1272 1929, Beilstein 6 H 961, 6 IV 6337.]
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