Methyl isoeugenol

Base Information

• Chemical Name: Methyl isoeugenol
• CAS No.: 93-16-3
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• Hs Code.: 29093090
• European Community (EC) Number: 202-224-6
• DSSTox Substance ID: DTXSID0052621
• Wikipedia: Methyl isoeugenol,Methyl_isoeugenol
• Mol file: 93-16-3.mol

Synonyms:Benzene,1,2-dimethoxy-4-(1-propenyl)- (9CI);Benzene, 1,2-dimethoxy-4-propenyl-(7CI,8CI);Veratrole, 4-propenyl- (6CI);1,2-Dimethoxy-4-(1-propenyl)benzene;1-(3,4-Dimethoxyphenyl)-1-propene;1-Veratryl-1-propene;3,4-Dimethoxy-b-methylstyrene;3-(3,4-Dimethoxyphenyl)-2-propene;4-(1-Propenyl)-1,2-dimethoxybenzene;4-Propenyl-1,2-dimethoxybenzene;4-Propenylveratrole;NSC 46111;O-Methylisoeugenol;

Chemical Property of Methyl isoeugenol

Chemical Property:

• Vapor Pressure: 0.011mmHg at 25°C
• Melting Point: 98-100 °C(lit.)
• Refractive Index: n20/D 1.568(lit.)
• Boiling Point: 271.1 °C at 760 mmHg
• Flash Point: 104.5 °C
• PSA: 18.46000
• Density: 0.998 g/cm³
• LogP: 2.73690
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

4-(1-Propenyl)-1,2-dimethoxybenzene >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/38:Irritating to eyes and skin.
• Hazard Codes: R36/38:Irritating to eyes and skin.
• Statements: 20/22-36/37/38-42
• Safety Statements: 22-26-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=CC1=CC(=C(C=C1)OC)OC
• General Description: Methyl isoeugenol is a minor component of essential oils and an FDA-approved food additive that undergoes oxidative metabolism in liver microsomes, producing metabolites such as 3'-hydroxymethylisoeugenol, isoeugenol, and reactive intermediates like 3'-oxomethylisoeugenol. The metabolic pathways vary across species (human, rat, bovine), with some metabolites potentially posing toxicological risks, warranting further study.

Technology Process of Methyl isoeugenol

There total 32 articles about Methyl isoeugenol 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: 97.0%

1-(3,4-dimethoxyphenyl)propan-1-ol (10548-83-1) → Methylisoeugenol (93-16-3)

Guidance literature:

With aluminum (III) chloride; triphenylphosphine; In nitromethane; at 80 ℃; for 2h;

DOI:10.1016/S1872-2067(15)61084-1

Reference yield: 86.0%

1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → Methylisoeugenol (93-16-3)

Guidance literature:

With potassium hydroxide; In butan-1-ol; for 12h; Reflux;

DOI:10.2174/1570180815666180620145609

Reference yield: 78.0%

1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) + pinacol vinylboronate (75927-49-0) → (E)-2-(3,4-dimethoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1618099-49-2) + Methylisoeugenol (93-16-3)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; for 1h; Temperature; Reagent/catalyst; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201402192

upstream raw materials:

1,2-dimethoxy-4-(2-propenyl)benzene

1-(3,4-dimethoxyphenyl)propan-1-ol

ethylmagnesium iodide

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

1-(3,4-dimethoxyphenyl)-2-nitropropene

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

6,7-dimethoxy-3-methyl-3,4-dihydro-isoquinoline; hydrochloride

4-(3,4-dimethoxy-phenyl)-5-methyl-[1,3]dioxane

Refernces

Metabolism of methylisoeugenol in liver microsomes of human, rat, and bovine origin

10.1124/dmd.111.038851

The research investigates the oxidative metabolism of methylisoeugenol, a minor constituent of essential oils and an FDA-approved food additive, using liver microsomes from human, rat, and bovine origins. The study aims to identify and quantify the metabolites formed, particularly focusing on potential reactive intermediates that could have adverse effects. Key chemicals involved in the research include methylisoeugenol itself, various reagents for synthesis and analysis such as acetone, CDCl3, dimethyl sulfoxide (DMSO), and NADPH-regenerating system components like glucose-6-phosphate dehydrogenase. The metabolites identified include 3'-hydroxymethylisoeugenol, isoeugenol, isochavibetol, 6-hydroxymethylisoeugenol, and others, with notable differences in metabolic patterns between species. The study highlights the formation of reactive metabolites such as 3'-oxomethylisoeugenol and 1',2'-dihydroxymethylisoeugenol, suggesting the need for further investigation into their potential toxicological implications.