| Identification | Back Directory | [Name]
Elemicin | [CAS]
487-11-6 | [Synonyms]
ELIMICIN
ELEMICIN
Elemicine
3,4,5-Trimethoxyallylbenzene
4-allyl-1,2,6-trimethoxybenzene
5-allyl-1,2,3-trimethoxy-benzen
5-ALLYL-1,2,3-TRIMETHOXYBENZENE
1-ALLYL-3,4,5-TRIMETHOXYBENZENE
1,2,3-Trimethoxy-5-allylbenzene
Benzene, 5-allyl-1,2,3-trimethoxy-
1-(3,4,5-TriMethoxyphenyl)-2-propene
3-(3,4,5-Trimethoxyphenyl)-1-propene
1,2,3-trimethoxy-5-prop-2-enylbenzene
1,2,3-trimethoxy-5-prop-2-enyl-benzene
1-(2-Propenyl)-3,4,5-trimethoxybenzene
1,2,3-TRIMETHOXY-5-(2-PROPENYL)BENZENE
1,2,3-trimethoxy-5-(2-propenyl)-benzen
5-(Prop-2-enyl)-1,2,3-triMethoxybenzene
Benzene, 5-(2-propenyl)-1,2,3-trimethoxy
1,2,3-trimethoxy-5-allylbenzene (elemicin)
1,2,3-TriMethoxy-5-(2-propen-1-yl)-benzene
Benzene,1,2,3-triMethoxy-5-(2-propen-1-yl)-
Elemicin, 5-(Prop-2-en-1-yl)-1,2,3-trimethoxybenzene
1,2,3-Trimethoxy-5-(2-propenyl)benzene
5-Allyl-1,2,3-trimethoxybenzene
elemicin,1,2,3-trimethoxy-5-allylbenzene,trimethoxyallylbenzene,elemicin | [EINECS(EC#)]
207-649-0 | [Molecular Formula]
C12H16O3 | [MDL Number]
MFCD01656688 | [MOL File]
487-11-6.mol | [Molecular Weight]
208.25 |
| Chemical Properties | Back Directory | [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 | [Major Application]
food and beverages
pharmaceutical | [InChI]
InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3 | [InChIKey]
BPLQKQKXWHCZSS-UHFFFAOYSA-N | [SMILES]
C1(OC)=CC(CC=C)=CC(OC)=C1OC | [LogP]
2.298 (est) | [NIST Chemistry Reference]
Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-(487-11-6) |
| Hazard Information | Back Directory | [Description]
Elemicin is a trioxygenated phenylpropane that has been found in A. dracunculus.1 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 CYP1A2.2 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 | [References]
[1] A. PAULI K K. Antimicrobial Properties of Volatile Phenylpropanes[J]. Natural Product Communications, 2010, 122 1. DOI: 10.1177/1934578x1000500910
[2] XIAO-NAN YANG. Metabolic Activation of Elemicin Leads to the Inhibition of Stearoyl-CoA Desaturase 1[J]. Chemical Research in Toxicology, 2019, 32 10: 1965-1976. DOI: 10.1021/acs.chemrestox.9b00112 |
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