| Identification | More | [Name]
Methyl eugenol | [CAS]
93-15-2 | [Synonyms]
1,2-DIMETHOXY-4-(2-PROPENYL)BENZENE
1-ALLYL-3,4-DIMETHOXYBENZENE
3-(3,4-DIMETHOXYPHENYL)-1-PROPENE
3,4-DIMETHOXYALLYLBENZENE
4-ALLYL-1,2-DIMETHOXYBENZENE
4-ALLYLVERATROLE
EUGENOL METHYL ETHER
EUGENYL METHYL ETHER
FEMA 2475
METHYL EUGENOL
TIMTEC-BB SBB007916
1-(3,4-Dimethoxyphenyl)-2-propene
1,2-dimethoxy-4-(2-propenyl)-benzen
1,2-Dimethoxy-4-allylbenzene
1,3,4-Eugenol methyl ether
1,3,4-eugenolmethylether
4-allyl-1,2-dimethoxy-benzen
4-Allyl-1,2-dimethyoxybenzene
Allyl veratrole
Allyl-1,2-dimethoxybenzene | [EINECS(EC#)]
202-223-0 | [Molecular Formula]
C11H14O2 | [MDL Number]
MFCD00008652 | [Molecular Weight]
178.23 | [MOL File]
93-15-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to pale yellow liquid. Spicy,
earthy odor. Bitter burning taste. This chemical is combustible. | [Melting point ]
-4 °C (lit.) | [Boiling point ]
254-255 °C (lit.) | [density ]
1.036 g/mL at 25 °C(lit.)
| [vapor pressure ]
0.463-1.983Pa at 25℃ | [FEMA ]
2475 | [refractive index ]
n20/D 1.534(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
0.5g/l | [form ]
Oil | [color ]
Colourless to Pale Yellow | [Odor]
at 1.00 % in dipropylene glycol. sweet fresh warm spicy clove carnation cinnamon | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [biological source]
synthetic | [Odor Type]
spicy | [Water Solubility ]
insoluble | [Merck ]
6073 | [BRN ]
1910871 | [Henry's Law Constant]
1.8×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
flavors and fragrances | [Cosmetics Ingredients Functions]
FRAGRANCE
PERFUMING | [InChI]
1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 | [InChIKey]
ZYEMGPIYFIJGTP-UHFFFAOYSA-N | [SMILES]
COc1ccc(CC=C)cc1OC | [LogP]
2.74-3.03 | [CAS DataBase Reference]
93-15-2(CAS DataBase Reference) | [IARC]
2B (Vol. 101) 2013 | [NIST Chemistry Reference]
Benzene, 1,2-dimethoxy-4-(2-propenyl)-(93-15-2) | [EPA Substance Registry System]
93-15-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS07,GHS08,GHS09 | [Signal word ]
Warning | [Hazard statements ]
H302-H341-H351-H411 | [Precautionary statements ]
P201-P273-P301+P312+P330-P308+P313 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
1
| [RTECS ]
CY2450000
| [TSCA ]
TSCA listed | [REACH Registrations]
Active | [HS Code ]
29093090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Chronic 2
Carc. 2
Muta. 2 | [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 | [Hazardous Substances Data]
93-15-2(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 1560 mg/kg (Jenner) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Eugenol-->4-Bromoveratrole-->Allyl toluene-4-sulfonate-->3,4-Dimethoxyphenylmagnesium bromide-->4-chloro-1,2-dimethoxy-benzene-->3,4-Dimethoxyphenylboronic acid, pinacol ester-->Allyl methyl ether-->Allyl methyl sulfide-->Allyltrimethylsilane-->1,2-Dimethoxybenzene | [Preparation Products]
Benzene,1,2,4-trimethoxy-5-(2-propenyl)--->FW 358.2-->4-trans-propenylveratrole-->Isoeugenylmethylether-->3,4-Dimethoxyphenylacetone-->2-Chloro-3-(3,4-dimethoxyphenyl)-1-propene-->23Epoxyeugenolmethylether |
| Hazard Information | Back Directory | [General Description]
Clear colorless to pale yellow liquid with a spicy earthy odor. Bitter burning taste. | [Reactivity Profile]
METHYLEUGENOL(93-15-2) is incompatible with strong oxidizers . May react exothermically with reducing agents to release hydrogen gas. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Possible carcinogen. | [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. | [Fire Hazard]
This chemical is combustible. | [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 qualified allergist, including careful exposure history and special testing may help diagnose skin or respiratory tract
allergy.
| [Shipping]
UN2810 Toxic liquids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required.
| [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 | [Chemical Properties]
Clear colorless to pale yellow liquid. Spicy,
earthy odor. Bitter burning taste. This chemical is combustible. | [Chemical Properties]
colourless to light yellow liquid | [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. | [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. | [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. | [Biochem/physiol Actions]
Taste at 1.5 ppm | [Carcinogenicity]
Methyleugenol is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals. | [Solubility in organics]
Soluble in alcohol and oils
| [storage]
Color Code—Green: General storage may be used.You should protect this material from exposure to light, andstore it under ambient temperatures | [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.] |
| Questions And Answer | Back Directory | [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. |
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