4-Vinylguaiacol (YMDB01624)

Identification

YMDB ID

YMDB01624

Name

4-Vinylguaiacol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

4-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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 number

7786-61-0

Weight

Average: 150.1745
Monoisotopic: 150.068079564

InChI Key

YOMSJEATGXXYPX-UHFFFAOYSA-N

InChI

InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3

IUPAC Name

4-ethenyl-2-methoxyphenol

Traditional IUPAC Name

2-methoxy-4-vinyl-phenol

Chemical Formula

C₉H₁₀O₂

SMILES

COC1=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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:42438 )
an aromatic compound (CPD-1072 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	7.42 g/L	ALOGPS
logP	1.84	ALOGPS
logP	2.25	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.03	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.19 m³·mol⁻¹	ChemAxon
Polarizability	15.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Clove	FDB000857
Curry	FDB000857
Peanut	FDB000857
Smoky	FDB000857
Spicy	FDB000857

SMPDB Pathways

Beer Reactions

PW002719

KEGG Pathways

Not Available

SMPDB Reactions

4-Vinylguaiacol + Carbon dioxide ↔ Ferulic acid + hydron

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udr-6900000000-c95e8007869a915d6fe6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udr-6900000000-c95e8007869a915d6fe6	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uki-2900000000-6a52b2fb0cd2b1888cba	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-8970000000-109c9889992939114454	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-9800000000-56d5ac2538cf6e556070	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-000i-9000000000-e8dab5adaa22e054ee21	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-0900000000-0ecf25f0ebb081e29570	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-001i-0900000000-90c9c5c165a18a64dbb3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-90c9c5c165a18a64dbb3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9100000000-4fc1449d3b5ebcebcddc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-07c85f81abcab35c8c85	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0c00-9200000000-e9c17a72d9b795c9cadc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-142267324f6352c647e4	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-9de02cce24e40d1314af	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1900000000-04be6d79c3fa5851d78d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9300000000-bab367ece5e140a11583	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-cd337f7259f32e912e8a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-5cef2e884a5445e8509b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00o0-7900000000-27870d0d63eeb1b6290d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-1900000000-3df4f1c76f8984133ce7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gdl-7900000000-5c60e1bd99afb019139f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9000000000-51462e1d8e8381a72712	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-e0b12c10ffeec106d759	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-dae1e2e32bbe62db4e5a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-6900000000-c0a65988d269dc5278a8	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0ug0-9700000000-32bccf98e351d8308924	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	42438
HMDB ID	HMDB0013744
Pubchem Compound ID	332
Kegg ID	C17883
ChemSpider ID	325
FOODB ID	FDB000857
Wikipedia ID	2-Methoxy-4-vinylphenol
BioCyc ID	Not Available

Enzymes

Protein Details

1. Ferulic acid decarboxylase 1

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

Structure for #<Compound:0xa06f42a8>

Enzymes

Reactions