Eugenol

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Eugenol Template:IPAc-en is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds.<ref name=pubchem/> It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Yield and Oil Composition of 38 Basil (Ocimum basilicum L.) Accessions Grown in Mississippi Template:Webarchive</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil.<ref name="herbmed">Template:Cite book</ref> Containing eugenol, clove essential oil is obtained from unopened clove buds.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Eugenol has a pleasant, spicy, clove-like scent.<ref>Template:Cite HMDB</ref> The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.<ref>Template:Cite journal</ref>

Biosynthesis

The biosynthesis of eugenol begins with the amino acid tyrosine. L-tyrosine is converted to p-coumaric acid by the enzyme tyrosine ammonia lyase (TAL).<ref>Template:Cite book</ref> From here, p-coumaric acid is converted to caffeic acid by p-coumarate 3-hydroxylase using oxygen and NADPH. S-Adenosyl methionine (SAM) is then used to methylate caffeic acid, forming ferulic acid, which is in turn converted to feruloyl-CoA by the enzyme 4-hydroxycinnamoyl-CoA ligase (4CL).<ref>Template:Cite journal</ref> Next, feruloyl-CoA is reduced to coniferaldehyde by cinnamoyl-CoA reductase (CCR). Coniferaldeyhyde is then further reduced to coniferyl alcohol by cinnamyl-alcohol dehydrogenase (CAD) or sinapyl-alcohol dehydrogenase (SAD). Coniferyl alcohol is then converted to an ester in the presence of the substrate CH3COSCoA, forming coniferyl acetate. Finally, coniferyl acetate is converted to eugenol via the enzyme eugenol synthase 1 and the use of NADPH.Template:Citation needed

Eugenol is a metabolite of caleicine, the active compound found in Calea ternifolia, and is thought to cause the sedative and hallucinogenic state C. ternifolia can induce.Template:Citation needed

File:Eugenol biosynthesis .tif
Biosynthesis of eugenol

Pharmacology

Eugenol and thymol possess general anesthetic properties. Like many other anesthetic agents, these 2-alkyl(oxy)phenols act as positive allosteric modulators of the GABAA receptor. Although eugenol and thymol are too toxic and not potent enough to be used clinically, these findings led to the development of 2-substituted phenol anesthetic drugs, including propanidid (later withdrawn) and the widely used propofol.<ref>Template:Cite journal</ref> Eugenol and the structurally similar myristicin have the common property of inhibiting MAO-A and MAO-B in vitro.<ref name="pmid15936201">Template:Cite journal</ref><ref name="essentialoilsafety">Template:Cite book</ref>

In humans, complete excretion occurs within 24 hour and metabolites are mostly conjugates of eugenol.<ref name="pmid2333717">Template:Cite journal</ref>

Uses

Humans

Eugenol is used as a flavor or aroma ingredient in teas, meats, cakes, perfumes, cosmetics, flavorings, and essential oils.<ref name="pubchem">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="livertox">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is also used as a local antiseptic and anaesthetic.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref> Eugenol can be combined with zinc oxide to form zinc oxide eugenol which has restorative and prosthodontic applications in dentistry. For persons with a dry socket as a complication of tooth extraction, packing the dry socket with a eugenol-zinc oxide paste on iodoform gauze is effective for reducing acute pain.<ref>Template:Cite journal</ref> Eugenol-zinc oxide paste is also used for root canal sealing.<ref name="Ferracane">Template:Cite book</ref>

Insects and fish

It 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.<ref>Template:Cite journal</ref> It also attracts female cucumber beetles.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Eugenol and isoeugenol, which both are floral volatile scent compounds, are catalyzed by a single type of enzyme in the genus Gymnadenia and the gene encoding for this enzyme is the first functionally characterized gene in these species.<ref name=Gupta>Template:Cite journal</ref> Eugenol is an ingredient in some insecticides.<ref name=pubchem/>

Clove oil is common as an anesthetic for use on aquarium fish as well as on wild fish when sampled for research and management purposes.<ref>Template:Cite conference</ref><ref>Template:Cite journal</ref> Where readily available, it presents a humane method to euthanize sick and diseased fish either by direct overdose or to induce sleep before an overdose of eugenol.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Template:Cite journal</ref>

Other

Eugenol is an ingredient in some fungicides and weed control products used in agricultural practices in the European Union.<ref name=pubchem/> It is used in hundreds of household products, such as pesticides, pet care, laundry, cleaning, and paper or vehicle products.<ref name=pubchem/>

Toxicity

Lesser side effects of eugenol toxicity that may not be considered a full overdose: Sedation, dizziness, hallucinations, delirium, mild respiratory depression, nausea, and muscle spasms.

Taken orally in high doses for chronic periods, eugenol may cause liver toxicity.<ref name=livertox/> An overdose is possible, causing a wide range of symptoms, such as hematuria (blood in urine), convulsions, diarrhea, unconsciousness, heavy respiratory depression, tachycardia (rapid heart rate), or acute kidney injury.<ref name=livertox/><ref>Template:Cite news</ref><ref>Template:Citation</ref> N-acetylcysteine may be used to treat people with eugenol or clove oil overdose.<ref>Template:Cite journal</ref>

As an allergenic

Eugenol is subject to restrictions on its use in perfumery,<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> as some people may become sensitised to it, however, the degree to which eugenol can cause an allergic reaction in humans is disputed.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Eugenol is a component of balsam of Peru, to which some people are allergic.<ref name="google1">Template:Cite book</ref><ref>Template:Cite book</ref> When eugenol is used in dental preparations such as surgical pastes, dental packing, and dental cement, it may cause contact stomatitis and allergic cheilitis.<ref name="google1"/> The allergy can be discovered via a patch test.<ref name="google1"/>

Natural occurrence

Eugenol naturally occurs in numerous plants, including the following: Template:Div col

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See also

References

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