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Methyleugenol (FDB008548)

Record Information
Version1.0
Creation date2010-04-08 22:08:08 UTC
Update date2020-09-17 15:31:40 UTC
Primary IDFDB008548
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethyleugenol
DescriptionMethyleugenol, also known as 4-allylveratrole, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying two methoxy groups. Methyleugenol is a sweet, anise, and apricot tasting compound. Outside of the human body, Methyleugenol is found in the highest concentration within a few different foods, such as allspices, tarragons, and sweet bay and in a lower concentration in sweet basils, rosemaries, and hyssops. Methyleugenol has also been detected, but not quantified, in several different foods, such as soybeans, evergreen blackberries, muskmelons, citrus, and pomes. As of October 2018, the US FDA withdrew authorization for the use of methyl eugenol as a synthetic flavoring substance for use in food because petitioners provided data demonstrating that these additives induce cancer in laboratory animals. FDA noted the action was despite its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use. Methyleugenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Methyl eugenol is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and it is important in the plant-insect interaction and pollination. Their ability to attract insects, particularly Bactrocera fruit flies was first noticed in 1915 by F. M. Howlett. The compound may have evolved in response to pathogens, as methyl eugenol has some antifungal activity. Methyl eugenol has been identified in a number of plants (over 450 species from 80 families including both angiosperm and gymnosperm families) and has a role in attracting pollinators. About 350 plant species have them as a component of floral fragrance.
CAS Number93-15-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.99ALOGPS
logP2.76ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.27 m³·mol⁻¹ChemAxon
Polarizability19.89 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H14O2
IUPAC name1,2-dimethoxy-4-(prop-2-en-1-yl)benzene
InChI IdentifierInChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3
InChI KeyZYEMGPIYFIJGTP-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C=C(CC=C)C=C1
Average Molecular Weight178.2277
Monoisotopic Molecular Weight178.099379692
Classification
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
  • 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 74.13%; H 7.92%; O 17.95%DFC
Melting PointFp -4°DFC
Boiling PointBp12 125-127°DFC
Experimental Water Solubility0.5 mg/mL at 25 oCCHEMICALS INSPECTION AND TESTING INSTITU (1992)
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-3900000000-6a0a17f77c5384cea66f2014-09-20View Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-24e258249ebb81a10db8Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-001i-6900000000-7eab85ab8f89486d0c67Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-511a7254b57b1693d125Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-6e7986f7be4dcc512bf5Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-001l-6900000000-0b489e050538331d3090Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-24e258249ebb81a10db8Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-001i-6900000000-7eab85ab8f89486d0c67Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-511a7254b57b1693d125Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-004i-6900000000-6e7986f7be4dcc512bf5Spectrum
GC-MSMethyleugenol, non-derivatized, GC-MS Spectrumsplash10-001l-6900000000-0b489e050538331d3090Spectrum
Predicted GC-MSMethyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g0-1900000000-ef346d457b34fcee14beSpectrum
Predicted GC-MSMethyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-0900000000-d41423501ff6a0caec1e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-006t-1910000000-c6bd5f4739dc2d3b4f992017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-5bcc530b76def442eca82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-7363ea03a8cd36e7f50a2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9600000000-8efff378856493d57d482016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-248b8d584ce0c311ffc02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-8e61ac867ff1e4b6bdd82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07cr-4900000000-e8817397f71772abc1752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-583273c8100f9e55b4bd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-0900000000-2884ce971c57cbd816d52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02u9-9800000000-4811899c7b2ebb02f8362021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-98bc20876c03ad8e0e922021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-0900000000-ba7858c7a47bbfdf0ab32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9400000000-86967ab180df17622b532021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider ID21106140
ChEMBL IDNot Available
KEGG Compound IDC10454
Pubchem Compound ID7127
Pubchem Substance IDNot Available
ChEBI ID4918
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31864
CRC / DFC (Dictionary of Food Compounds) IDHGZ80-F:DNB75-W
EAFUS ID1331
Dr. Duke ID3,4-DIMETHOXY-ALLYL-BENZENE|METHYL-EUGENOL|EUGENOL-METHYL-ETHER
BIGG IDNot Available
KNApSAcK IDC00002741
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID93-15-2
GoodScent IDrw1008291
SuperScent ID7127
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 / Bioactivities
DescriptorIDDefinitionReference
anestheticDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antidote50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
anti feedantDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti radicularDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
DNA-binderDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
fungistatDUKE
hypothermicDUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
myorelaxantDUKE
narcotic35482 A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
clove
  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
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice
  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
creamy
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
oily
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
anise
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
balsam
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
chocolate
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cinnamon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
mesquite
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
musty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
apricot
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
banana
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
coconut
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
peach
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
plum
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
raspberry
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
carnation
  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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.