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Record Information
Version1.0
Created at2020-03-19 00:48:11 UTC
Updated at2020-12-07 19:07:36 UTC
CannabisDB IDCDB000640
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethyl isoeugenol
DescriptionMethyl isoeugenol belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying two methoxy groups. Methyl isoeugenol also belongs to the class of organic compounds known as phenyl propanoid. Methylisoeugenol is a mild, bitter, and clove tasting compound. It is the methyl ether derivative of isoeugenol, found in certain essential oils. Methyl Isoeugenol is naturally occurring and found in the essential oils of plants such as nutmegs, star anises, and gingers, ajowan caraway and allspice (PMID: 19259498 ). It can occur as both (E)- and (Z)-isomers. It has also been detected, but not quantified, in several different foods, such as sweet basils, carrots, ceylon cinnamons, wild carrots, and tarragons. Methylisoeugenol has also been reported to be a volatile component in cannabis samples (PMID: 26657499 ).
Structure
Thumb
Synonyms
Chemical FormulaC11H14O2
Average Molecular Weight178.23
Monoisotopic Molecular Weight178.0994
IUPAC Name1,2-dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene
Traditional Name(Z)-methyl isoeugenol
CAS Registry Number6379-72-2
SMILES
COC1=C(OC)C=C(\C=C/C)C=C1
InChI Identifier
InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-
InChI KeyNNWHUJCUHAELCL-PLNGDYQASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Styrene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point16 - 17 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.47ALOGPS
logP2.78ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.34 m³·mol⁻¹ChemAxon
Polarizability19.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMethyl isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03fs-1900000000-3d41a0d29a7363963fbbSpectrum
Predicted GC-MSMethyl isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0041553
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021536
KNApSAcK IDC00050779
Chemspider ID21242881
KEGG Compound IDC10478
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl isoeugenol
METLIN IDNot Available
PubChem Compound1549045
PDB IDNot Available
ChEBI ID50550
References
General References
  1. Park IK, Kim J, Lee SG, Shin SC: Nematicidal Activity of Plant Essential Oils and Components From Ajowan (Trachyspermum ammi), Allspice (Pimenta dioica) and Litsea (Litsea cubeba) Essential Oils Against Pine Wood Nematode (Bursaphelenchus Xylophilus). J Nematol. 2007 Sep;39(3):275-9. [PubMed:19259498 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Only showing the first 10 proteins. There are 25 proteins in total.

Only showing the first 10 proteins. There are 25 proteins in total.