Isoeugenol is a
phenylpropene
Phenylpropene is the organic compound with the formula C6H5CH2CH=CH2. It is a colorless liquid. The compound consists of a phenyl group attached to allyl. Phenylpropene isomerizes to trans-propenylbenzene.
In plant biochemistry, the phenylprop ...
, a propenyl-substituted
guaiacol
Guaiacol () is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing an methoxy functional group. Guaiacol appears as a viscous colorless oil, although aged or impure samples are often yellowish. It occurs wid ...
. A phenylpropanoid, it occurs in the
essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
s of plants such as
ylang-ylang
''Cananga odorata'', known as ylang-ylang ( ) or cananga tree, is a tropical tree that is native to the Philippines, Malaysia, Indonesia, New Guinea, the Solomon Islands, and Queensland, Australia. It is also native to parts of Thailand and Viet ...
(''Cananga odorata''), and is a component of wood smoke and
liquid smoke
Liquid smoke is a water-soluble yellow to red liquid used as a flavoring as a substitute for Smoking (cooking), cooking with wood smoke while retaining a similar flavor. It can be used to flavor any meat or vegetable. It is generally made by Cond ...
. It can be synthesized from
eugenol
Eugenol is an allyl chain-substituted guaiacol, 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, nutmeg, cinnamon, basil ...
and has been used in the manufacture of
vanillin
Vanillin is an organic compound with the molecular formula . It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin is now used ...
. It may occur as either the cis ''(Z)'' or trans ''(E)''
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
. Trans ''(E)'' isoeugenol is crystalline while cis ''(Z)'' isoeugenol is a liquid. Isoeugenol is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses.
Allergy
Some individuals experience a hives-like reaction to long-term exposure to Isoeugenol, which is named as ''Fragrance'' in the ingredients of consumer products such as soaps, shampoos and detergents, bath tissue, and topical cosmetic applications. Sensitivity to isoeugenol (Fragrance) may be identified with a clinical patch test.
See also
*
Pseudoisoeugenol
Pseudoisoeugenol is a naturally occurring phenylpropene and an isomer of eugenol.
Natural occurrence and derivatives
Pseudoisoeugenol naturally occurs in the essential oils of roots from plants within the genus ''Pimpinella''. In addition to its ...
*
Methylisoeugenol
Methyl isoeugenol (isomethyleugenol) is a phenylpropanoid, the methyl ether of isoeugenol, found in certain essential oils. It can occur as both (''E'')- and (''Z'')-isomers.
See also
* Methyl eugenol
Methyl eugenol (allylveratrol) is a na ...
*
Desmethylisoeugenol
Hydroxychavicol is a phenylpropanoid compound present in leaves of ''Piper betle''. It is a more potent inhibitor of xanthine oxidase (IC50=16.7 µM) than allopurinol.
Research
It might be a useful new compound in treating cutaneous fungal inf ...
References
{{Phenylpropene
Phenylpropenes
O-methylated natural phenols