| Description |
Methyleugenol (ME) (4-alkyl-1, 2-dimethoxybenzene-carboxylate) is a natural chemical compound classified as a type of phenylpropanoid and it is the methyl ether of eugenol. ME is a widely distributed natural plant product and occurs in > 200 plant species in 32 families found mainly in the tropics. It is consumed by humans and animals in many plants and fruits (e.g., anise, nutmeg, basil, blackberry essence, bananas, and citrus), and ME is a yellowish, oily, naturally occurring liquid with a clove-like aroma and is present in many essential oils. |
| Application |
ME is used as a flavouring agent in jellies, baked goods, non-alcoholic beverages, chewing gum, candy, puddings, relishes and ice cream and it is also widely used as a fragrance ingredient in perfumes (0.3-0.8%), creams and lotions (0.01-0.05%), toiletries and detergents. Moreover, ME has been used as an anaesthetic in rodents and it also is used as an insect attractant in combination with insecticides.
Methyleugenol is also a component of several essential oils that are sold for use in aromatherapy, massage oils and alternative medicines. Some essential oils, including citronella (Cymbopogon spp.), basil (Ocimum spp.), bay (Laurus nobilis) and tea tree (Melaleuca spp.), which may contain a high percentage of methyleugenol are used as fragrances in consumer products, such as personal care products and household cleaners. For example, citronella oil, which may contain methyleugenol, is an active ingredient in some commercially available personal insect repellent lotions and sprays that are applied to the skin and it is also used in outdoor candles and torches as an ambient insect repellent. |
| Chemical Properties |
colourless to light yellow liquid |
| Chemical Properties |
Clear colorless to pale yellow liquid. Spicy, earthy odor. Bitter burning taste. This chemical is combustible. |
| Chemical Properties |
Eugenol Methyl Ethe occurs in numerous essential oils, sometimes at a very high concentration. The ether is an almost colorless liquid with a mild-spicy, slightly herbal odor. It is prepared by methylation of eugenol and is used in perfumery (e.g., in carnation and lilac compositions) and in flavor compositions. |
| Chemical Properties |
Eugenyl methyl ether has a delicate clove-carnation odor with a bitter, burning taste. |
| Occurrence |
Reported in the essential oils of Myrtaceae and Luraceae; it was identifed originally in the essential oil from roots of Asarum europaeum L and Asarum canadense L Subsequently, it was identifed as the main constituent of the oil from wood of Dacrydium franklinii Hook (97 5%), in Melaleuca bracteata F v M (leaves, 90 to 95%), in Cinnamomum oliveri Bail (leaves, 90 to 95%), and as a minor constituent in the oils of betel, citronella, Japanese calamus, pimenta, hyacinth, rose, basil, bay, cajeput and others Reported found in heated blackberry, pepper, lovage seed, chervil, lemon balm, alpinia species, clove buds, nutmeg, pepper, mace, tarragon, Ocimum sanctum, laurel, myrtle leaf and berry, rosemary, pimento berry and mastic gum leaf oil |
| Uses |
Fragrance ingredient in perfumes, toiletries and detergents; flavor ingredient in baked goods. |
| Preparation |
Usually prepared by methylation of eugenol. |
| Aroma threshold values |
Detection: 68 ppb to 8 5 ppm. |
| Taste threshold values |
Taste characteristics at 5.0 ppm: spice, cinnamon and clove, mouth tingle, fresh, peppery and woody. |
| General Description |
Clear colorless to pale yellow liquid with a spicy earthy odor. Bitter burning taste. |
| Air & Water Reactions |
Insoluble in water. |
| Reactivity Profile |
Methyl eugenol is incompatible with strong oxidizers . May react exothermically with reducing agents to release hydrogen gas. |
| Hazard |
Possible carcinogen. |
| Fire Hazard |
Methyl eugenol is combustible. |
| Safety Profile |
Confirmed carcinogen. Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. Some other alkenylbenzenes have carcinogenic activity. See also EUGENOL, ALLYL COMPOUNDS, and ETHERS |
| Potential Exposure |
Methyl eugenol is a naturally occurring substance found in the essential oils of several plant species. Methyleugenol is used as a flavoring agent in jellies, baked goods, nonalcoholic beverages, chewing gum, candy, pudding, relish, and ice cream. Methyleugenol has been used as an anesthetic in rodents. It also is used as an insect attractant in combination with insecticides. |
| Carcinogenicity |
Methyleugenol is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals. |
| Shipping |
UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. |
| Purification Methods |
Recrystallise the ether from hexane at low temperature and redistil it (preferably in vacuo). [Hillmer & Schorning Z Phys Chem [A] 167 407 1934, Briner & Fliszár Helv Chim Acta 42 2063 1959, Beilstein 6 H 963, 6 IV 6337.] |
| Incompatibilities |
Methyleugenol is Incompatible with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with reducing agents may cause the release of hydrogen gas |
| Waste Disposal |
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. |
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