Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:44 UTC |
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Update date | 2019-11-26 02:55:32 UTC |
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Primary ID | FDB000857 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 2-Methoxy-4-vinylphenol |
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Description | 2-Methoxy-4-vinylphenol, also known as 4-vinylguaiacol or 4-ethenyl-2-methoxyphenol, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methoxy-4-vinylphenol exists in all eukaryotes, ranging from yeast 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, carrots, and red wines and in a lower concentration in sesames, beers, and kohlrabis. 2-Methoxy-4-vinylphenol has also been detected, but not quantified in, several different foods, such as spearmints, tortilla chips, citrus, oats, and sweet oranges. This could make 2-methoxy-4-vinylphenol a potential biomarker for the consumption of these foods. |
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CAS Number | 7786-61-0 |
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Structure | |
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Synonyms | Synonym | Source |
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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 | 4-Vinyl-2-methoxyphenol ( P-vinylguaiacol) | HMDB | 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 |
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Predicted Properties | |
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Chemical Formula | C9H10O2 |
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IUPAC name | 4-ethenyl-2-methoxyphenol |
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InChI Identifier | InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 |
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InChI Key | YOMSJEATGXXYPX-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC(C=C)=CC=C1O |
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Average Molecular Weight | 150.1745 |
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Monoisotopic Molecular Weight | 150.068079564 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Methoxyphenols |
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Direct Parent | Methoxyphenols |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 71.98%; H 6.71%; O 21.31% | DFC |
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Melting Point | Mp 57° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | 312 (e 8900) (MeOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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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 | 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 | 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 | MS | Mass Spectrum (Electron Ionization) | splash10-0ug0-9700000000-32bccf98e351d8308924 | JSpectraViewer | MoNA |
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External Links |
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ChemSpider ID | 325 |
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ChEMBL ID | CHEMBL1232595 |
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KEGG Compound ID | C17883 |
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Pubchem Compound ID | 332 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 632 |
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DrugBank ID | DB03514 |
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HMDB ID | HMDB13744 |
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CRC / DFC (Dictionary of Food Compounds) ID | BRG84-D:BKH58-G |
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EAFUS ID | 2225 |
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Dr. Duke ID | P-VINYL-GUAIACOL|4-VINYL-GUAIACOL|2-METHOXY-4-VINYL-PHENOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00029546 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 7786-61-0 |
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GoodScent ID | rw1005101 |
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SuperScent ID | 332 |
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Wikipedia ID | 2-Methoxy-4-vinylphenol |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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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 |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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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.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
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