1,2,3-trimethoxy-5-(prop-2-en-1-yl)benzene

• ChemBase ID: 88109
• Molecular Formular: C12H16O3
• Molecular Mass: 208.25364
• Monoisotopic Mass: 208.10994437
• SMILES: O(c1cc(cc(c1OC)OC)CC=C)C
• Canonical SMILES: C=CCc1cc(OC)c(c(c1)OC)OC
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,2,3-trimethoxy-5-(prop-2-en-1-yl)benzene
• IUPAC Traditional name: elemicin
• Synonyms: Elemicin; 1,2,3-Trimethoxy-5-(2-propen-1-yl)-benzene; 5-Allyl-1,2,3-trimethoxybenzene; 1-(3,4,5-Trimethoxyphenyl)-2-propene; 3,4,5-Trimethoxyallylbenzene; 5-(Prop-2-enyl)-1,2,3-trimethoxybenzene; Elemicin; 5-(Prop-2-en-1-yl)-1,2,3-trimethoxybenzene; 5-Allyl-1,2,3-trimethoxybenzene

Database IDs

• CAS Number: 487-11-6
• PubChem SID: 162075148
• PubChem CID: 10248
• CHEMBL: 458690
• Chemspider ID: 9830
• KEGG ID: C10451
• Wikipedia Title: Elemicin

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.5988028
• LogD (pH = 7.4): 2.5988028
• Log P: 2.5988028
• Molar Refractivity: 59.7349 cm^3
• Polarizability: 23.16213 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Clear Colorless Oil

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Flammable

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Uncontrolled

DETAILS

Toronto Research Chemicals - E501020

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.

REFERENCES

• Baser, K., et al.: Flavour Fragr. J., 8, 35 (1993)
• McKenna, A., et al.: Eur J Emerg Med., 11, 240 (1993)