4-Vinylphenol (YMDB01627)

Identification

YMDB ID

YMDB01627

Name

4-Vinylphenol

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

4-Vinylphenol is a vinylphenol, a type of pyranoanthocyanin. 4-Vinylphenol is produced by decarboxylation by phenyl acrylic acid decarboxylase of the grape compound p-coumaric 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-Vinylphenol is responsible for a hospital or plaster smell. [PMID: 17303275]

Structure

MOL SDF PDB SMILES InChI

Synonyms

4-Hydroxystyrene
p-Vinylphenol
4-Vinylphenol
p-Hydroxystyrene

CAS number

2628-17-3

Weight

Average: 120.1485
Monoisotopic: 120.057514878

InChI Key

FUGYGGDSWSUORM-UHFFFAOYSA-N

InChI

InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2

IUPAC Name

4-ethenylphenol

Traditional IUPAC Name

4-vinylphenol

Chemical Formula

C₈H₈O

SMILES

OC1=CC=C(C=C)C=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:1883 )
a small molecule (CPD-1075 )

Physical Properties

State

Solid

Charge

Melting point

73.5 °C

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	8.4 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.41	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.73 m³·mol⁻¹	ChemAxon
Polarizability	13.15 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

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

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 - GC-EI-TOF (Non-derivatized)	splash10-0006-0900000000-78e97f8689a1bddce8d1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004l-1900000000-aabb90db206495e1949c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0006-0900000000-78e97f8689a1bddce8d1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004l-1900000000-aabb90db206495e1949c	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-e4b2ae72210dba8376c5	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fu-8900000000-96525d05990bd44a73e6	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 , negative	splash10-014i-0900000000-4748791daa3cc6db33cb	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-b529604eb0086ce7d85a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-cc4e2accb5dbfca1223a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9300000000-1a680f497983265f7000	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-992515c0effcfff51739	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-adf06e57ffef41aa20d0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-9600000000-7855fd6420cc0a980f56	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-2c381eb3871f5dbd6a94	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-9800000000-e2093cd31e1a5d12f825	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v00-9000000000-dd7dfadb6034e83a56c0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-972f865a96261dcb891a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-3900000000-cc2986e6d45482e40a36	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i2d-9000000000-6a5b5c88ab894e1f7233	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
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	1883
HMDB ID	HMDB04072
Pubchem Compound ID	13493582
Kegg ID	C05627
ChemSpider ID	56234
FOODB ID	FDB010540
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xaf7f2254>