93-15-2 Usage
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
Different sources of media describe the Occurrence of 93-15-2 differently. You can refer to the following data:
1. 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.
2. 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
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 93-15-2 differently. You can refer to the following data:
1. colourless to light yellow liquid
2. Clear colorless to pale yellow liquid. Spicy,
earthy odor. Bitter burning taste. This chemical is combustible.
3. 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.
4. Eugenyl methyl ether has a delicate clove–carnation odor with a bitter, burning taste.
Uses
Different sources of media describe the Uses of 93-15-2 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
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.
Carcinogenicity
Methyleugenol is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
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
Check Digit Verification of cas no
The CAS Registry Mumber 93-15-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 93-15:
(4*9)+(3*3)+(2*1)+(1*5)=52
52 % 10 = 2
So 93-15-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O2.C2H6O/c1-3-4-8-5-6-9(11)10(7-8)12-2;1-3-2/h3,5-7,11H,1,4H2,2H3;1-2H3
93-15-2Relevant articles and documents
One-Pot Biocatalytic In Vivo Methylation-Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L-DOPA
Birmingham, William R.,Galman, James L.,Parmeggiani, Fabio,Seibt, Lisa,Turner, Nicholas J.
, (2022/01/13)
Electron-rich phenolic substrates can be derived from the depolymerisation of lignin feedstocks. Direct biotransformations of the hydroxycinnamic acid monomers obtained can be exploited to produce high-value chemicals, such as α-amino acids, however the reaction is often hampered by the chemical autooxidation in alkaline or harsh reaction media. Regioselective O-methyltransferases (OMTs) are ubiquitous enzymes in natural secondary metabolic pathways utilising an expensive co-substrate S-adenosyl-l-methionine (SAM) as the methylating reagent altering the physicochemical properties of the hydroxycinnamic acids. In this study, we engineered an OMT to accept a variety of electron-rich phenolic substrates, modified a commercial E. coli strain BL21 (DE3) to regenerate SAM in vivo, and combined it with an engineered ammonia lyase to partake in a one-pot, two whole cell enzyme cascade to produce the l-DOPA precursor l-veratrylglycine from lignin-derived ferulic acid.
Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups
Cook, Adam,MacLean, Haydn,St. Onge, Piers,Newman, Stephen G.
, p. 13337 - 13347 (2021/11/20)
We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.
Specific Residues Expand the Substrate Scope and Enhance the Regioselectivity of a Plant O-Methyltransferase
Tang, Qingyun,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.
, p. 3227 - 3233 (2019/07/04)
An isoeugenol 4-O-methyltransferase (IeOMT), isolated from the plant Clarkia breweri, can be engineered to a caffeic acid 3-O-methyltransferase (CaOMT) by replacing three consecutive residues. Here we further investigated functions of these residues by constructing the triple mutant T133M/A134N/T135Q as well as single mutants of each residue. Phenolics with different chain lengths and different functional groups were investigated. The variant T133M improves the enzymatic activities against all tested substrates by providing beneficial interactions to residues which directly interact with the substrate. Mutant A134N significantly enhanced the regioselectivity. It is meta-selective or even specific against most of the tested substrates but para-specific towards 3,4-dihydroxybenzoic acid. The triple mutant T133M/A134N/T135Q benefits from these two mutations, which not only expand the substrate scope but also enhance the regioselectivity of IeOMT. On the basis of our work, regiospecific methylated phenolics can be produced in high purity by different IeOMT variants.
