Isoeugenol is a propenyl-substituted

guaiacol Guaiacol () is an organic compound with the formula C6H4(OH)(OCH3). It is a phenolic compound containing a methoxy functional group. Guaiacol appears as a viscous colorless oil, although aged or impure samples are often yellowish. It occurs wid ...

. A

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...

, 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 ...

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 Vie ...

(''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 cooking with wood smoke while retaining a similar flavor. It can be used to flavor any meat or vegetable. It is available as pure condensed smoke from ...

. 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, ...

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 ethanolic extract of the vanilla bean. Synthetic vanillin ...

. It may occur as either the cis ''(Z)'' or trans ''(E)''

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

. 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.

References

{{Phenylpropene Phenylpropenes O-methylated natural phenols