Showing Compound 2-Methoxy-4-vinylphenol (FDB000857)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:44 UTC

Update date

2019-11-26 02:55:32 UTC

Primary ID

FDB000857

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Methoxy-4-vinylphenol

Description

2-Methoxy-4-vinylphenol, also known as 4-hydroxy-3-methoxystyrene or 4-vinylguaiacol, 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. 2-Methoxy-4-vinylphenol exists in all eukaryotes, ranging from yeast to plants to humans. 2-Methoxy-4-vinylphenol is a clove, curry, and peanut tasting compound. 2-Methoxy-4-vinylphenol is found, on average, in the highest concentration within a few different foods, such as wild carrots (Daucus carota), carrots (Daucus carota ssp. sativus), and red wine and in a lower concentration in white wine, coffees (Coffea), and robusta coffees (Coffea canephora). 2-Methoxy-4-vinylphenol has also been detected, but not quantified in, several different foods, such as taco, citrus, celery stalks (Apium graveolens var. dulce), evergreen blackberries (Rubus laciniatus), and tortilla chip. This could make 2-methoxy-4-vinylphenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Methoxy-4-vinylphenol.

CAS Number

7786-61-0

Structure

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

Synonyms

Synonym	Source
2-(4-Hydroxy-3-methoxyphenyl)ethene	ChEBI
2m4VP	ChEBI
4-Ethenyl-2-methoxyphenol	ChEBI
4-Hydroxy-3-methoxyphenylethene	ChEBI
4-Hydroxy-3-methoxystyrene	ChEBI
4-Hydroxy-3-methoxyvinylbenzene	ChEBI
4-Vinyl-2-methoxyphenol	ChEBI
4-Vinylguaiacol	ChEBI
O-Methoxy-p-vinylphenol	ChEBI
p-Vinylguaiacol	ChEBI
Para-vinylguaiacol	ChEBI
2-Methoxy-4-vinyl-phenol	HMDB
2-Methoxy-4-vinylphenol (4-vinylguaiacol)	HMDB
2-Methoxy-4-vinylphenol (vinylguaiacol)	HMDB
2-Methoxy-vinylphenol	HMDB
2-Metoxy-4-vinyl-phenol	HMDB
4-Ethenyl-2-methoxy-phenol	HMDB
4-Ethenylguaiacol	HMDB
4-Vinyl-2-methoxyphenol ( P-vinylguaiacol)	HMDB
4-Vinyl-2-methoxyphenol (4-vinylguaiacol)	HMDB
4-Vinyl-O-guaiacol	HMDB
4-Vinylguaiacole	HMDB
Guaiacol, 4-vinyl	HMDB
P-Vinyl guaicol	HMDB
Phenol, 2-methoxy-4-ethenyl	HMDB
Phenol, 4-vinyl, 2-methoxy	HMDB
Vinylguaiacol	HMDB
Vinylguaiacol (4-vinyl-2-methoxyphenol)	HMDB
Vinylguajacol	HMDB
2-Methoxy-4-Vinyl-Phenol	biospider
2-Methoxy-4-vinylphenol	db_source
2-metoxy-4-vinyl-phenol	biospider
4-Vinyl guaiacol	biospider
4-vinyl-2-methoxyphenol	biospider
EUG	biospider
Hesperetol	db_source
O-methoxy-p-vinylphenol	biospider
P-vinyl guaiacol	biospider
P-vinyl guaicol	biospider
P-vinylguaiacol	biospider
Phenol, 4-ethenyl-2-methoxy-	biospider
Vinylcatechol-o-methyl ether, p-	biospider

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H10O2

IUPAC name

4-ethenyl-2-methoxyphenol

InChI Identifier

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

InChI Key

YOMSJEATGXXYPX-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC(C=C)=CC=C1O

Average Molecular Weight

150.1745

Monoisotopic Molecular Weight

150.068079564

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biofluid and excreta:

Urine

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 71.98%; H 6.71%; O 21.31%	DFC
Melting Point	Mp 57°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	312 (e 8900) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0ug0-9700000000-32bccf98e351d8308924	Spectrum
GC-MS	2-Methoxy-4-vinylphenol, non-derivatized, GC-MS Spectrum	splash10-0udr-6900000000-c95e8007869a915d6fe6	Spectrum
GC-MS	2-Methoxy-4-vinylphenol, non-derivatized, GC-MS Spectrum	splash10-0udr-6900000000-c95e8007869a915d6fe6	Spectrum
Predicted GC-MS	2-Methoxy-4-vinylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uki-2900000000-6a52b2fb0cd2b1888cba	Spectrum
Predicted GC-MS	2-Methoxy-4-vinylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-8970000000-109c9889992939114454	Spectrum
Predicted GC-MS	2-Methoxy-4-vinylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-9800000000-56d5ac2538cf6e556070	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-000i-9000000000-e8dab5adaa22e054ee21	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-0900000000-0ecf25f0ebb081e29570	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-001i-0900000000-90c9c5c165a18a64dbb3	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0900000000-90c9c5c165a18a64dbb3	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9100000000-4fc1449d3b5ebcebcddc	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-07c85f81abcab35c8c85	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0c00-9200000000-e9c17a72d9b795c9cadc	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-142267324f6352c647e4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-9de02cce24e40d1314af	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1900000000-04be6d79c3fa5851d78d	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9300000000-bab367ece5e140a11583	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-cd337f7259f32e912e8a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-5cef2e884a5445e8509b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00o0-7900000000-27870d0d63eeb1b6290d	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-1900000000-3df4f1c76f8984133ce7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gdl-7900000000-5c60e1bd99afb019139f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9000000000-51462e1d8e8381a72712	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-e0b12c10ffeec106d759	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1900000000-dae1e2e32bbe62db4e5a	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-6900000000-c0a65988d269dc5278a8	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

632

DrugBank ID

DB03514

HMDB ID

HMDB13744

CRC / DFC (Dictionary of Food Compounds) ID

BRG84-D:BKH58-G

EAFUS ID

2225

Dr. Duke ID

P-VINYL-GUAIACOL|4-VINYL-GUAIACOL|2-METHOXY-4-VINYL-PHENOL

BIGG ID

Not Available

KNApSAcK ID

C00029546

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

7786-61-0

GoodScent ID

rw1005101

SuperScent ID

332

Wikipedia ID

2-Methoxy-4-vinylphenol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti edemic			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti prostaglandin	49020	A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
pheromone	26013	A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
clove	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
curry	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
peanut	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
smoky	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.