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Identification
YMDB IDYMDB01624
Name4-Vinylguaiacol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description4-Vinylguaiacol is a vinylphenol, a type of pyranoanthocyanin. 4-Vinylguaiacol is produced by enzymatic decarboxylation of the grape compound ferulic acid by certain strains of S. cerevisiae. Vinylphenols then spontaneously condensate with grape anthocyanins (mainly malvidin-3-O-glucoside) to form pigments important for the color of ageing wine. 4-Vinylguaiacol is also found in beers and is responsible for a pungent clove-like aroma. [PMID: 17303275]
Structure
Thumb
Synonyms
  • 2-methoxy-4-vinylphenol (4-vinylguaiacol)
  • 2-methoxy-4-vinylphenol (vinylguaiacol)
  • 2-Methoxy-vinylphenol
  • 2-metoxy-4-vinyl-phenol
  • 4-ethenyl-2-methoxyphenol
  • 4-Hydroxy-3-methoxystyrene
  • 4-Vinyl-2-methoxyphenol
  • 4-vinyl-2-methoxyphenol ( p-vinylguaiacol)
  • 4-Vinyl-2-methoxyphenol (4-vinylguaiacol)
  • 4-Vinylguaiacol
  • 4-Vinylguaiacole
  • guaiacol, 4-vinyl
  • o-methoxy-p-vinylphenol
  • p-Vinyl guaicol
  • p-Vinylguaiacol
  • para-vinylguaiacol
  • Phenol, 2-methoxy-4-ethenyl
  • Phenol, 2-methoxy-4-vinyl-
  • Phenol, 4-ethenyl-2-methoxy-
  • Phenol, 4-vinyl, 2-methoxy
  • vinylguaiacol (4-vinyl-2-methoxyphenol)
  • 2-(4-Hydroxy-3-methoxyphenyl)ethene
  • 2m4VP
  • 4-Hydroxy-3-methoxyphenylethene
  • 4-Hydroxy-3-methoxyvinylbenzene
  • 2-Methoxy-4-vinyl-phenol
  • 4-Ethenyl-2-methoxy-phenol
  • 4-Ethenylguaiacol
  • 4-Vinyl-O-guaiacol
  • Vinylguaiacol
  • Vinylguajacol
CAS number7786-61-0
WeightAverage: 150.1745
Monoisotopic: 150.068079564
InChI KeyYOMSJEATGXXYPX-UHFFFAOYSA-N
InChIInChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3
IUPAC Name4-ethenyl-2-methoxyphenol
Traditional IUPAC Name2-methoxy-4-vinyl-phenol
Chemical FormulaC9H10O2
SMILESCOC1=C(O)C=CC(C=C)=C1
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
  • Styrene
  • 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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.42 g/LALOGPS
logP1.84ALOGPS
logP2.25ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.19 m³·mol⁻¹ChemAxon
Polarizability15.99 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
CloveFDB000857
CurryFDB000857
PeanutFDB000857
SmokyFDB000857
SpicyFDB000857
SMPDB Pathways
Beer ReactionsPW002719 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
4-Vinylguaiacol + Carbon dioxideFerulic acid + hydron
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • McMurrough, I., Madigan, D., Donelly, D., Hurley, J.,Doyle, AM., Heenigan, G., McNulty, N. and Smyth, MR. (1996) "Control of Ferulic Acid and 4-Vinyl Guaicol in Brewing." Journal of the Institute of Brewing 102:5, pg 327-332
  • 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 ID42438
HMDB IDHMDB0013744
Pubchem Compound ID332
Kegg IDC17883
ChemSpider ID325
FOODB IDFDB000857
Wikipedia ID2-Methoxy-4-vinylphenol
BioCyc IDNot Available

Enzymes

General function:
ferulate metabolic process
Specific function:
Catalyzes the reversible decarboxylation of aromatic carboxylic acids like ferulic acid, p-coumaric acid or cinnamic acid, producing the corresponding vinyl derivatives 4-vinylphenol, 4-vinylguaiacol, and styrene, respectively, which play the role of aroma metabolites (PubMed:20471595, PubMed:25647642). Not essential for ubiquinone synthesis (PubMed:20471595).
Gene Name:
FDC1
Uniprot ID:
Q03034
Molecular weight:
56163.39
Reactions