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-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. |
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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 | 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 |
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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 | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0ug0-9700000000-32bccf98e351d8308924 | 2015-03-01 | View 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 |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-000i-9800000000-56d5ac2538cf6e556070 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive | splash10-000i-9000000000-e8dab5adaa22e054ee21 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a4i-0900000000-0ecf25f0ebb081e29570 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative | splash10-001i-0900000000-90c9c5c165a18a64dbb3 | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-001i-0900000000-90c9c5c165a18a64dbb3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-000i-9100000000-4fc1449d3b5ebcebcddc | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-07c85f81abcab35c8c85 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0c00-9200000000-e9c17a72d9b795c9cadc | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-142267324f6352c647e4 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900000000-9de02cce24e40d1314af | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-1900000000-04be6d79c3fa5851d78d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-9300000000-bab367ece5e140a11583 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-cd337f7259f32e912e8a | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-5cef2e884a5445e8509b | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00o0-7900000000-27870d0d63eeb1b6290d | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0uxr-1900000000-3df4f1c76f8984133ce7 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gdl-7900000000-5c60e1bd99afb019139f | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-9000000000-51462e1d8e8381a72712 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-e0b12c10ffeec106d759 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1900000000-dae1e2e32bbe62db4e5a | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-6900000000-c0a65988d269dc5278a8 | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum |
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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 | | An agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention. | DUKE | Anti-inflammatory | 35472 | An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis. | DUKE | Anti prostaglandin | 49020 | An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort. | DUKE | Name | 48318 | flavor | DUKE | Perfumery | 48318 | The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties. | DUKE | Prostaglandin synthesis inhibitor | 35222 | An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs). | DUKE | Pheromone | 26013 | A chemical signal that triggers biological responses, influencing behavior, reproduction, and social interactions. Therapeutically, pheromones have applications in anxiety and stress management, as well as mood regulation, with potential medical uses in treating disorders such as anxiety and depression. | 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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