Methyl eugenol

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.

Occurrence

Methyl eugenol is not very common in higher concentrations in the essential oils of Ocimum species. However, 20% methyl eugenol has been found in the oil of O. sanctum (Hegnauer 1966). Methyl eugenol has been detected as the main compound in an essential oil of O.basilicum var. minimum of Taiwanese origin (42.9-64.3%) and in the stem oil of O.basilicum (53.1%) of the same origin (Cheng and Liu 1983). In an oil of O.gratissimum of Brazilian origin, 46.8% methyl eugenol was found (Vostrowsky 1990). A high methyl eugenol concentration (24.7%) was reported by Brophy and Jogia (1986) from plant material of O.basilicum grown locally in Fiji.

Application

Methyl eugenol 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.

Description

Clear colorless to pale yellow liquid. Spicy,earthy odor. Bitter burning taste. This chemical is combustible. Molecular weight = 178.23; Specific gravity 5 1.0396at 20℃; Vapor density 5 .1.0; Boiling point = 249℃;254.7℃ at 760 mmHg; Melting point 5 2 4℃; Vaporpressure 5 0.02 mmHg at 20℃; 1 mmHg at 85℃; Flashpoint 5 99℃; 109℃. Hazard Identification (based on NFPA704 M Rating System): Health 2; Flammability 1; Reactivity0. Practically insoluble in water; solubility 5 ,1 mg/mL at66
F; 500 mg/L.

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

Methyleugenol is a phenylpropene that is commonly found in plants such as nutmeg, pimento, lemongrass, tarragon, basil, star anise, and fennel. Methyleugenol has been shown to inhibit histone deacetylase (HDAC) activity in the human colon carcinoma cell line HT29. Compounds that exhibit HDAC-inhibitory properties or disrupt the HDAC complex have potential applications in cancer therapy and chemoprevention. In addition, Methyleugenol is a flavoring agent often used in consumer products such as jellies, baked goods, beverages,chewing gums, ice cream, and fragrance.

Uses

Methyl eugenol may be used as an analytical reference standard for the quantification of the analyte in the following:????????

• Essential oil of Pimenta pseudocaryophyllus using high-performance liquid chromatography (HPLC). The purity of the extracted compound is then determined by gas chromatography coupled to flame ionization detector (GC/FID).???????
• Stem bark of Cinnamomum zeylanicum Blume using reversed-phase high-performance liquid chromatography (RP-HPLC) with UV-visible detection.???????
• Rosa hybrida using gas-chromatography coupled to mass spectrometry (GC-MS) technique.

Uses

Fragrance ingredient in perfumes, toiletries and detergents; flavor ingredient in baked goods.

Definition

ChEBI: O-methyleugenol is a phenylpropanoid. It is functionally related to a eugenol.

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.

Biochem/physiol Actions

Taste at 1.5 ppm

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.

First aid

Eyes: Consideration should be given to the skin,eyes, and respiratory tract (lung function tests) in any placement or periodic examinations. Evaluation by a qualifiedallergist, including careful exposure history and special testing, may help diagnose skin or respiratory tract allergy.

Carcinogenicity

Methyleugenol is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

storage

Color Code—Green: General storage may be used.You should protect this material from exposure to light, andstore it under ambient temperatures

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.