ISOEUGENOL

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.

Description

Isoeugenol is an essential oil that was originally isolated from the Asian tree ylang-ylang (Cananga odorata). It exists in trans and cis isomeric forms; the more common trans isomer is shown here. Its first reported preparation was the isomerization of eugenol by two German research groups in 1891. The acetate ester of isoeugenol?can be used to prepare vanillin.
Isoeugenol is a flavor component of the nutmeg in the pumpkin pie you’ll eat on Thanksgiving. Its isomer eugenol is a flavor component of clove. For an excellent and almost correct explanation of the difference between the two, go to?nbclearn.com.
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Chemical properties

light yellow-green viscous liquid

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

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.

The Uses of ISOEUGENOL

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.

The Uses of ISOEUGENOL

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).

The Uses of ISOEUGENOL

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).

Background

Isoeugenol is a commonly used fragrance added to many commercially available products, and occurs naturally in the essential oils of plants such as ylang-ylang. It is also a significant dermatologic sensitizer and allergen, and as a result has been restricted to 200 p.p.m. since 1998 according to guidelines issued by the fragrance industry . Allergic reactivity to Isoeugenol may be identified with a patch test.

Indications

Isoeugenol is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

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.

Metabolism

Not Available