Methyleugenol

Base Information

• Chemical Name: Methyleugenol
• CAS No.: 93-15-2
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• Hs Code.: 29093090
• European Community (EC) Number: 202-223-0
• NSC Number: 209528,8900
• UN Number: 2810
• UNII: 29T9VA6R7M
• DSSTox Substance ID: DTXSID5025607
• Nikkaji Number: J4.669H
• Wikipedia: Methyl eugenol,Methyl_eugenol
• Wikidata: Q419829
• NCI Thesaurus Code: C44401
• RXCUI: 1368373
• Metabolomics Workbench ID: 45164
• ChEMBL ID: CHEMBL108861
• Mol file: 93-15-2.mol

Synonyms:1-allyl-3,4-dimethoxybenzene;4-allyl-1,2-dimethoxybenzene;eugenol methyl ether;methyl eugenol;methyleugenol

Chemical Property of Methyleugenol

Chemical Property:

• Appearance/Colour: colourless to light yellow liquid
• Vapor Pressure: 0.000652mmHg at 25°C
• Melting Point: -4 °C(lit.)
• Refractive Index: n20/D 1.534(lit.)
• Boiling Point: 254.7 °C at 760 mmHg
• Flash Point: 135.1 °C
• PSA: 18.46000
• Density: 0.98 g/cm³
• LogP: 2.43230
• Storage Temp.: 2-8°C
• Solubility.: 0.5g/l
• Water Solubility.: insoluble
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 156
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Methyl eugenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-40
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: COC1=C(C=C(C=C1)CC=C)OC
• 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.
• 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. 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. Fragrance ingredient in perfumes, toiletries and detergents; flavor ingredient in baked goods.

Technology Process of Methyleugenol

There total 33 articles about Methyleugenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-Bromoveratrole (2859-78-1) + C10H20AlNO → 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2)

Guidance literature:

bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 60 ℃; for 12h;

DOI:10.1055/s-2003-41492

Reference yield: 95.0%

4-allylguaiacol (97-53-0) + dimethyl sulfate (77-78-1) → 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(98)00885-5

Reference yield: 95.0%

4-allylguaiacol (97-53-0) + methyl iodide (74-88-4) → 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 12h;

DOI:10.2174/1570180815666180620145609

upstream raw materials:

1,2-dimethoxybenzene

allyl iodid

4-allylguaiacol

dimethyl sulfate

Downstream raw materials:

6,7-dimethoxy-1-(4-methoxy-phenyl)-3-methyl-3,4-dihydro-isoquinoline

1-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-3-methyl-3,4-dihydro-isoquinoline

1-allyl-2,4,5-trimethoxybenzene

3,4-dimethoxyphenylacetaldehyde

Refernces

• 1、 Nunes, Daiana O. S.,Vinturelle, Rafaelle,Martins, Francislene J.,dos Santos, Thiago F.,Valverde, Alessandra Leda,Ribeiro, Carlos Magno R.,Castro, Helena C.,Folly, Evelize. "Biotechnological Potential of Eugenol and Thymol Derivatives Against Staphylococcus aureus from Bovine Mastitis". . p. 1846 - 1855. Retrieved 2021/04/29.
• 2、 Sudarma,Shofiati,Darmayanti. "Nitration of methyl eugenol derived from clove oil". . p. 17 - 20. Retrieved 2019/12/12.