|Molar mass||164.20 g/mol|
|Melting point||−7.5 °C (18.5 °F; 265.6 K)|
|Boiling point||254 °C (489 °F; 527 K)|
|Acidity (pKa)||10.19 at 25 °C|
|Flash point||104 °C (219 °F; 377 K)|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Eugenol // is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a colorless to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil.
Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. Eugenol can be combined with zinc oxide to form a material – known as zinc oxide eugenol – which has restorative and prosthodontic applications in dentistry. For example, zinc oxide eugenol is used for root canal sealing It can be used to reduce the presence of Listeria monocytogenes and Lactobacillus sakei in food. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Attempts have been made to develop eugenol derivatives for intravenous injection, such as propanidid and G.29.505. The latter produced unacceptable side effects around the site of injection in many patients. It is one of many compounds that is attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. It also attracts female cucumber beetle. It is recently discovered that eugenol and isoeugenol, floral volatile scent compounds, are catalyzed by single type of enzyme in Gymnadenia species and gene encoding for this enzyme is first functionally characterized gene in this species so far.
It is commonly used in wisdom tooth extraction surgeries complicated by dry socket. 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. Where readily available, it presents a humane method to euthanise sick and diseased fish either by direct over-dose or to induce sleep before an overdose of ethanol. It is also used in some mousetraps and kills certain human colon cancer cell lines in vitro and in vivo. Eugenol may have potential therapeutic effects against diseases characterized by excessive osteoclast activity. 
Eugenol is hepatotoxic, meaning it may cause damage to the liver. Overdose is possible, causing a wide range of symptoms from blood in the patient's urine, to convulsions, diarrhoea, nausea, unconsciousness, dizziness, or rapid heartbeat. According to a published 1993 report, a 2-year old boy nearly died after taking between 5 and 10 ml. Eugenol is subject to restrictions on its use in perfumery as some people may become sensitised to it, however, the degree to which eugenol can cause an allergic reaction in humans is disputed.
Eugenol is a component of Balsam of Peru, to which some people are allergic. When eugenol is used in dental preparations such as surgical pastes, dental packing, and dental cement, it may cause contact stomatitis and allergic cheilitis. The allergy can be discovered via a patch test.
List of plants that contain the chemical
- Cloves (Syzygium aromaticum)
- Cinnamomum tamala
- Nutmeg (Myristica fragrans)
- Ocimum basilicum – Sweet Basil
- Ocimum gratissimum – African Basil
- Ocimum tenuiflorum (Ocimum sanctum) – Tulsi or Holy Basil
- Japanese star anise
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