Description
Isoeugenol is a phenylpropene, a propenyl-substituted guaiacol
existing in some essential oils of plants. It is produced by plants
as defense compounds against animals and microorganisms and as
floral attractants of pollinators. It can also be used as inhibitors
of lipid peroxidation and as free radicals scavenger. Because of its
antimicrobial properties as well as pleasing aromas and flavors,
humans, since antiquity, have used plant material containing
phenylpropenes to preserve and flavor their food.
References
Koeduka, Takao, et al. "Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester." Proceedings of the National Academy of Sciences 103.26 (2006): 10128-10133.
Rajakumar, D. V., and M. N. A. Rao. "Dehydrozingerone and isoeugenol as inhibitors of lipid peroxidation and as free radical scavengers." Biochemical pharmacology 46.11 (1993): 2067-2072.
Description
Isoeugenol has a floral odor reminiscent of carnation. May be
prepared by the alkaline isomerization of eugenol obtained from
essential oils high in eugenol.
Chemical Properties
Isoeugenol occurs in many essential oils, mostly with eugenol,
but not as the main component. Commercial isoeugenol is a mixture of (E)- and
(Z)-isomers, in which the (E)-isomer dominates because it is thermodynamically
more stable. Isoeugenol is a yellowish, viscous liquid with a fine clove odor, with
that of the crystalline trans-isomer being the more delicate.
Isoeugenol can be hydrogenated catalytically to form dihydroeugenol. Vanillin
was formerly prepared by oxidation of isoeugenol. Additional fragrance materials
are prepared by esterification or etherification of the hydroxy group.
Isoeugenol can be hydrogenated catalytically to form dihydroeugenol. Vanillin
was formerly prepared by oxidation of isoeugenol. Additional fragrance materials
are prepared by esterification or etherification of the hydroxy group.
Chemical Properties
light yellow-green viscous liquid
Chemical Properties
Isoeugenol has a floral odor reminiscent of carnation.
Occurrence
The commercial product is a mixture of cis- and trans-isomers; reported found in the essential oils of ylangylang and nutmeg; also in the oil from flowers of Michelia champaca and in the oil from seeds of Nectandra puchury. Reported found
in bilberry, guava, blackberry, tomato, cinnamon, clove bud and stem, nutmeg, mace, thymus, tea, coffee, fatty fish, beer, rum, plum,
mushroom, dill, malt wort, elder flower, cuttlefish, Chinese quince, pimento leaf and maté.
Uses
Isoeugenol is used inmanufacture of vanillin; perfumes; flavoring; fragrance in perfumery, over-the-counter medicines, dental materials, foods; some
perfumery uses (soap gardenia; coffee; abronea; tuberose; jonquil); natural occurrence (nutmeg oil).
Uses
isoeugenol is a volatile oil fraction derived from eugenol. It is also found in ylang-ylang and nutmeg oils. It is used in cosmetics as a fragrance or to mask odor.
Uses
Isoeugenol may be used as an analytical reference standard for the determination of the analyte in bioconversion broth using reversed-phase high-performance liquid chromatography with ultraviolet detection (RP-HPLC-UV).
Definition
ChEBI: A phenylpropanoid that is an isomer of eugenol in which the allyl substituent is replaced by a prop-1-enyl group.
Preparation
The starting material for the synthesis of isoeugenol is eugenol.The
sodium or potassium salt of eugenol is isomerized to isoeugenol by heating. Isomerization
can also be achieved catalytically in the presence of ruthenium [346]
or rhodium compounds.
Aroma threshold values
Detection: 100 ppb
Taste threshold values
Taste characteristics at 10 ppm: sweet spice and clove with woody and phenolic nuances.
General Description
Pale yellow oily liquid with a spice-clove odor. Freezes at 14°F. Density 1.08 g / cm3. Occurs in ylang-ylang oil and other essential oils.
Air & Water Reactions
Slightly water soluble .
Fire Hazard
ISOEUGENOL is combustible.
Contact allergens
Isoeugenol is a mixture of two cis and trans isomers.
It occurs in ylang-ylang and other essential oils. It is a
common allergen of perfumes and cosmetics such as
deodorants and is contained in fragrance mix. Its presence
in cosmetics is indicated in the INGREDIENTS
series. Substitution by esters such as isoeugenyl acetate
(not indicated on the package) does not always
resolve the allergenic problem, because of the in vivo
hydrolysis of the substitute into isoeugenol.
Synthesis
By the alkaline isomerization of eugenol obtained from essential oils high in eugenol.
