Elemicin

Base Information

• Chemical Name: Elemicin
• CAS No.: 487-11-6
• Molecular Formula: C12H16O3
• Molecular Weight: 208.257
• Hs Code.: 2909309090
• European Community (EC) Number: 207-649-0
• NSC Number: 16704
• UNII: HSZ191AKAN
• DSSTox Substance ID: DTXSID60197586
• Nikkaji Number: J6.017H
• Wikipedia: Elemicin
• Wikidata: Q417746
• Metabolomics Workbench ID: 46204
• ChEMBL ID: CHEMBL458690
• Mol file: 487-11-6.mol

Synonyms:elemicin

Chemical Property of Elemicin

Chemical Property:

• Appearance/Colour: Colorless oil-like liquid
• Vapor Pressure: 0.00666mmHg at 25°C
• Refractive Index: 1.496
• Boiling Point: 279.8 °C at 760 mmHg
• Flash Point: 92.6 °C
• PSA: 27.69000
• Density: 1.011 g/cm³
• LogP: 2.44090
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 179

Purity/Quality:

99.9% ^*data from raw suppliers

Elemicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)CC=C
• Description: Elemicin is a trioxygenated phenylpropane that has been found in A. dracunculus. It is active against S. aureus, B. subtilis, and C. albicans (MICs = 600, 2,500, and 1,000 mg/L, respectively) but not E. coli, K. pneumoniae, P. aeruginosa (MICs = >8,000 mg/L for all), or L. monocytogenes (MIC = >3,000 mg/L). Elemicin is toxic to mice following metabolic activation to 1’-hydroxyelemicin by the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2. It increases plasma and hepatic triglyceride levels, decreases stearoyl-CoA desaturase 1 (Scd1) expression, and induces hepatomegaly in mice when administered at a dose of 500 mg/kg per day for three weeks.
• Uses: A constituent of the essential oil of nutmeg and is responsible for the psychoactive effects of nutmeg. Also a minor constituent of the oleoresin and essential oil of Manila elemi (Canarium luzonicum). Exhibits anticholinergic-like effects in humans.

Technology Process of Elemicin

There total 22 articles about Elemicin 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: 96.0%

4-allyl-2,6-dimethoxyphenol (6627-88-9) + methyl iodide (74-88-4) → elemicin (487-11-6)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 24h;

DOI:10.1002/jccs.200400144

Reference yield: 95.0%

5-allyl-2,3-dimethoxyphenol + methyl iodide (74-88-4) → elemicin (487-11-6)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1055/s-0034-1378395

Reference yield: 93.0%

4-allyl-2,6-dimethoxyphenol (6627-88-9) + dimethyl sulfate (77-78-1) → elemicin (487-11-6)

Guidance literature:

With potassium hydroxide; for 4.5h;

DOI:10.1002/adsc.200700072

upstream raw materials:

4-allyl-2,6-dimethoxyphenol

dimethyl sulfate

5-Hydroxyeugenol

1,3-dimethoxy-2-[(prop-2-en-1-yl)oxy]benzene

Downstream raw materials:

2,2-dichloro-3-(3,4,5-trimethoxybenzyl)cyclobutanone

C₂₀H₂₂O₅

3-methoxy-4,5-methylenedioxybenzaldehyde

Refernces

• 1、 Berti, Liliane,Bolla, Jean Michel,Brunel, Jean Michel,Dedieu, Luc,Lorenzi, Vanina,Muselli, Alain. "Antibacterial mode of action of the daucus carota essential oil active compounds against campylobacter jejuni and efflux-mediated drug resistance in gram-negative bacteria". . . Retrieved 2020.
• 2、 Chang, Dong-Jo,Kim, Wan-Joo. "Discovery of structurally simplified analogs of colchicine as an immunosuppressant". . p. 3121 - 3125. Retrieved 2014/06/24.