Eugenol: Difference between revisions
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{{Short description|A phenylpropene, an allyl chain-substituted guaiacol}} | |||
{{Chemical compound}} | |||
== | ==Eugenol== | ||
Eugenol | [[File:Eugenol_biosynthesis_.tif|thumb|right|Eugenol biosynthesis pathway]] | ||
Eugenol is a [[phenylpropene]], a type of [[phenylpropanoid]] compound, and is a member of the [[allylbenzene]] class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from [[clove oil]], [[nutmeg]], [[cinnamon]], [[basil]], and [[bay leaf]]. It is used in perfumes, flavorings, and in medicine as a local antiseptic and anesthetic. | |||
==Chemical properties== | |||
Eugenol has the [[chemical formula]] C__H__O_. It is an allyl chain-substituted [[guaiacol]]. Eugenol is slightly soluble in water and soluble in organic solvents. It has a [[boiling point]] of 254 °C and a [[density]] of 1.06 g/cm_. | |||
==Biosynthesis== | |||
Eugenol is biosynthesized from the [[amino acid]] [[phenylalanine]] via the [[shikimate pathway]]. The biosynthesis involves the conversion of phenylalanine to [[cinnamic acid]], which is then converted to [[p-coumaric acid]], followed by the formation of [[caffeic acid]]. Caffeic acid is then converted to [[ferulic acid]], which is the direct precursor of eugenol. The enzyme [[eugenol synthase]] catalyzes the final step in the biosynthesis of eugenol from ferulic acid. | |||
==Uses== | ==Uses== | ||
Eugenol | Eugenol is widely used in the [[perfume]] and [[flavoring]] industries due to its pleasant aroma. In the medical field, it is used as a local antiseptic and anesthetic. Eugenol is also used in [[dentistry]] for its analgesic and antiseptic properties, often in the form of [[zinc oxide eugenol]] cement. | ||
== | ==Safety== | ||
Eugenol is | Eugenol is generally recognized as safe when used in small amounts as a flavoring agent. However, it can be toxic in large doses and may cause [[allergic reactions]] in some individuals. It is important to handle eugenol with care, as it can cause irritation to the skin and eyes. | ||
== | ==Related pages== | ||
* [[ | * [[Phenylpropene]] | ||
* [[Essential oil]] | * [[Essential oil]] | ||
* [[ | * [[Clove oil]] | ||
* [[ | * [[Shikimate pathway]] | ||
[[Category:Phenylpropanoids]] | [[Category:Phenylpropanoids]] | ||
[[Category: | [[Category:Perfume ingredients]] | ||
[[Category: | [[Category:Flavoring agents]] | ||
Latest revision as of 11:03, 15 February 2025
A phenylpropene, an allyl chain-substituted guaiacol
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This chemical compound related article is a stub.
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Eugenol[edit]
Eugenol is a phenylpropene, a type of phenylpropanoid compound, and is a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil, and bay leaf. It is used in perfumes, flavorings, and in medicine as a local antiseptic and anesthetic.
Chemical properties[edit]
Eugenol has the chemical formula C__H__O_. It is an allyl chain-substituted guaiacol. Eugenol is slightly soluble in water and soluble in organic solvents. It has a boiling point of 254 °C and a density of 1.06 g/cm_.
Biosynthesis[edit]
Eugenol is biosynthesized from the amino acid phenylalanine via the shikimate pathway. The biosynthesis involves the conversion of phenylalanine to cinnamic acid, which is then converted to p-coumaric acid, followed by the formation of caffeic acid. Caffeic acid is then converted to ferulic acid, which is the direct precursor of eugenol. The enzyme eugenol synthase catalyzes the final step in the biosynthesis of eugenol from ferulic acid.
Uses[edit]
Eugenol is widely used in the perfume and flavoring industries due to its pleasant aroma. In the medical field, it is used as a local antiseptic and anesthetic. Eugenol is also used in dentistry for its analgesic and antiseptic properties, often in the form of zinc oxide eugenol cement.
Safety[edit]
Eugenol is generally recognized as safe when used in small amounts as a flavoring agent. However, it can be toxic in large doses and may cause allergic reactions in some individuals. It is important to handle eugenol with care, as it can cause irritation to the skin and eyes.
