Record Information
Version1.0
Creation date2010-04-08 22:15:28 UTC
Update date2019-11-26 03:19:52 UTC
Primary IDFDB021092
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethoxyeugenol
DescriptionMethoxyeugenol, also known as 4-allylsyringol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Methoxyeugenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Methoxyeugenol is a sweet, bacon, and burnt tasting compound. Methoxyeugenol has been detected, but not quantified in, herbs and spices. This could make methoxyeugenol a potential biomarker for the consumption of these foods.
CAS Number6627-88-9
Structure
Thumb
Synonyms
SynonymSource
2,6-Dimethoxy-4-(2-propenyl)-phenolHMDB
2,6-Dimethoxy-4-(2-propenyl)phenol, 9ciHMDB
2,6-Dimethoxy-4-allylphenolHMDB
2,6-DimethoxychavicolHMDB
4-(2-Propenyl)-2,6-dimethoxyphenolHMDB
4-Allyl-2,6-dimethoxy-phenolHMDB
4-Allyl-2,6-dimethoxyphenolHMDB
4-Allyl-2,6-dimethoxyphenol, 8ciHMDB
4-Allyl-2,6-dimetoxyphenolHMDB
4-AllylsyringolHMDB
4-Hydroxy-3,5-dimethoxyallylbenzeneHMDB
N-AllylcyclohexylamineHMDB
Phenol, 2,6-dimethoxy-4-(2-propenyl)- (9ci)HMDB
Phenol, 4-(2-propenyl)-2,6-dimethoxyHMDB
Phenol, 4-allyl-2,6-dimethoxy- (8ci)HMDB
2,6-Dimethoxy-4-(2-propenyl)phenolMeSH
6-MethoxyeugenolMeSH
2,6-Dimethoxy-4-(2-propenyl)phenol, 9CIdb_source
4-(2-Propenyl)-2,6-dimethoxyphenol (4-allylsyringol)biospider
4-Allyl-2,6-dimethoxyphenol, 8CIdb_source
4-allyl-2,6-dimetoxyphenolbiospider
Methoxyeugenoldb_source
N-allylcyclohexylaminebiospider
Phenol, 2,6-dimethoxy-4-(2-propenyl)-biospider
Phenol, 2,6-dimethoxy-4-(2-propenyl)- (9CI)biospider
Phenol, 4-allyl-2,6-dimethoxy-biospider
Phenol, 4-allyl-2,6-dimethoxy- (8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility1.59 g/LALOGPS
logP2.23ALOGPS
logP2.45ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.34ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.25 m³·mol⁻¹ChemAxon
Polarizability20.54 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H14O3
IUPAC name2,6-dimethoxy-4-(prop-2-en-1-yl)phenol
InChI IdentifierInChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3
InChI KeyFWMPKHMKIJDEMJ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(CC=C)=CC(OC)=C1O
Average Molecular Weight194.2271
Monoisotopic Molecular Weight194.094294314
Classification
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.02%; H 7.26%; O 24.71%DFC
Melting PointNot Available
Boiling PointBp2 123-125°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fvl-1900000000-6bb088a84e5d530fd6a9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0umi-6290000000-ddd8fa9b2271b5e885faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-bf95219cde86264ddd0eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-b3789d49cb1d02ff5e01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-7900000000-2b4993fb9c656f50c42fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-1cb6aa76e853c97dffa4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-7a91ae9052ae5aad302cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6s-3900000000-2d0b6fcc14c0098a2b40JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID196968
ChEMBL IDCHEMBL2059292
KEGG Compound IDNot Available
Pubchem Compound ID226486
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB41194
CRC / DFC (Dictionary of Food Compounds) IDNKV52-U:NKV54-W
EAFUS ID104
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID6627-88-9
GoodScent IDrw1037281
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
flower
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
roasted
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
burnt
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
meaty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bacon
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
smoky
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ham
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference