You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB01613
Name4-Allyl-2-methoxyphenol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEugenol, also known as 4-allylguaiacol or 1,3,4-eugenol, 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. Eugenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Eugenol exists in all eukaryotes, ranging from yeast to humans. Eugenol is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1-Hydroxy-2-methoxy-4-allylbenzene
  • 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene
  • 1-Hydroxy-2-methoxy-4-propenylbenzene
  • 1,3,4-Eugenol
  • 1'-Acetoxyeugenol acetate
  • 2-Hydroxy-5-allylanisole
  • 2-Methoxy-1-hydroxy-4-allylbenzene
  • 2-Methoxy-4-(2-propenyl)phenol
  • 2-Methoxy-4-(2-propenyl)phenyl
  • 2-Methoxy-4-(3-propenyl)phenol
  • 2-methoxy-4-(prop-2-en-1-yl)phenol
  • 2-Methoxy-4-allylphenol
  • 2-Methoxy-4-prop-2-enylphenol
  • 2-Metoksy-4-allilofenol
  • 4-(2-Propenyl)-2-methoxyphenol (eugenol)
  • 4-(Acetyloxy)-alpha-ethenyl-3-methoxybenzenemethanol acetate
  • 4-Allyl-1-hydroxy-2-methoxybenzene
  • 4-allyl-2-methoxy-Phenol
  • 4-allyl-2-methoxyphenol
  • 4-allyl-2-methoxyphenol (eugenol)
  • 4-Allyl-2-rnethoxyphenol (eugenol)
  • 4-Allylcatechol 2-methyl ether
  • 4-Allylcatechol-2-methyl ether
  • 4-Allylguaiacol
  • 4-Hydroxy-3-methoxy-1-allylbenzene
  • 4-Hydroxy-3-methoxyallylbenzene
  • 5-Allylguaiacol
  • Allylguaiacol
  • Caryophyllic acid
  • Engenol
  • Eugenic acid
  • Eugenol
  • Eugenol (2-Methoxy-4-(2-propenyl)phenol)
  • Eugenol (natural)
  • Eugenol [usan]
  • P-allylguaiacol
  • P-eugenol
  • Phenol, 2-methoxy-4-(2-propenyl)-
  • Phenol, 4-allyl-2-methoxy-
  • Synthetic eugenol
  • 1-Allyl-3-methoxy-4-hydroxybenzene
  • 1-Allyl-4-hydroxy-3-methoxybenzene
  • 2-Methoxy-4-(2-propen-1-yl)phenol
  • Caryophyllate
  • Eugenate
CAS number97-53-0
WeightAverage: 164.2011
Monoisotopic: 164.083729628
InChI KeyRRAFCDWBNXTKKO-UHFFFAOYSA-N
InChIInChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
IUPAC Name2-methoxy-4-(prop-2-en-1-yl)phenol
Traditional IUPAC Nameeugenol
Chemical FormulaC10H12O2
SMILESCOC1=CC(CC=C)=CC=C1O
Chemical Taxonomy
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
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point-9.1 °C
Experimental Properties
PropertyValueReference
Water Solubility2.46 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP2.27 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP2.66ALOGPS
logP2.61ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.79 m³·mol⁻¹ChemAxon
Polarizability17.9 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
CinnamonFDB012171
CloveFDB012171
HoneyFDB012171
SpicyFDB012171
SweetFDB012171
WoodyFDB012171
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID4917
HMDB IDHMDB05809
Pubchem Compound ID3314
Kegg IDC10427
ChemSpider ID13876103
FOODB IDFDB012171
Wikipedia IDEugenol
BioCyc IDNot Available