Elemicin Chemical Properties

Boiling point:

152-156 °C

Density 

1.0630 g/cm3

storage temp. 

Amber Vial, -20°C Freezer

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Oil

color 

Colourless

Odor

at 100.00 %. spice flower

Odor Type

spicy

Stability:

Light Sensitive

LogP

2.298 (est)

NIST Chemistry Reference

Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-(487-11-6)

Safety Information

HS Code 

2909309090

Elemicin Usage And Synthesis

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.

Chemical Properties

Clear Colorless Oil

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.

Definition

ChEBI: Elemicin is an olefinic compound.

Synthesis

Prod. :
1) by isolation from Elemi oil (high-boiling fractions).
2) from Dimcthylpyrogallol plus Allyl bromide, via 2,6-Dimethyl pyrogallol allylether. This is heated in a Claisen-rearrangement reaction to yield 4-Hydroxy-3,5-dimethoxy allylbenzene. The latter is methylated to yield Elemicine.
3) From Eugenol via 5-Hydroxyeugenol.

target

Antifection

Elemicin(487-11-6)Related Product Information

• (Trifluoromethoxy)benzene
• 1,2,3-Trimethoxybenzene
• m-Anisyl alcohol
• Anisole
• METHYLSTYRENE
• Allyl chloride
• PROPYLENE
• 4-Methoxyphenylacetic acid
• Triallylamine
• Allyl glycidyl ether
• 1,2,4-Trimethoxybenzene
• 3-(METHOXYMETHOXY)BENZALDEHYDE
• p-Anisaldehyde
• Allyl bromide
• o-Anisaldehyde
• Allyl alcohol
• Tangeretin
• 3-Anilino-2-(3,4,5-triMethoxybenzyl)acrylonitrile, (Mixture of cis/trans isoMers)