2-Methoxy-4-vinylphenol: Difference between revisions

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| IUPACName = 4-Ethenyl-2-methoxyphenol
| IUPACName = 4-Ethenyl-2-methoxyphenol
| OtherNames = 4-Hydroxy-3-methoxystyrene<br>4-Vinylguaiacol<br>p-Vinylguaiacol<br>p-Vinicatechol-o-methyl ether
| OtherNames = 4-Hydroxy-3-methoxystyrene<br>4-Vinylguaiacol<br>p-Vinylguaiacol<br>p-Vinicatechol-o-methyl ether
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DA069CTH0O
| UNII = DA069CTH0O
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
Line 22: Line 22:
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 7786-61-0
| CASNo = 7786-61-0
| CASOther =
| CASNoOther =
| PubChem = 332
| PubChem = 332
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 325
| ChemSpiderID = 325
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03514
| DrugBank = DB03514
| SMILES = Oc1ccc(cc1OC)C=C
| SMILES = Oc1ccc(cc1OC)C=C
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=9|H=10|O=2
| C=9 | H=10 | O=2
| Appearance =
| ExactMass = 150.06808 u
| Appearance =
| Density =
| Density =
| MeltingPtC =
| MeltingPtC =
| BoilingPtC = 224
| BoilingPtC = 224
| Solubility =
| Solubility =
}}
}}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| ExternalMSDS =
| ExternalSDS =
| EUClass =
| EUClass =
| NFPA-H = | NFPA-F = | NFPA-R =
| NFPA-H = | NFPA-F = | NFPA-R =
| FlashPtC = 113
| FlashPtC = 113
| RPhrases =
| RPhrases =
| SPhrases =
| SPhrases =
| AutoignitionC =
| AutoignitionPtC =
}}
}}
}}
}}


'''2-Methoxy-4-vinylphenol''' is an aromatic substance used as a flavoring agent.<ref>[http://www.inchem.org/documents/jecfa/jeceval/jec_1395.htm 2-METHOXY-4-VINYLPHENOL], Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives</ref> It is one of the compounds responsible for the natural aroma of [[buckwheat]].<ref>{{cite journal
'''2-Methoxy-4-vinylphenol''' is an aromatic substance used as a flavoring agent.<ref>[http://www.inchem.org/documents/jecfa/jeceval/jec_1395.htm 2-METHOXY-4-VINYLPHENOL], Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives</ref> It is one of the compounds responsible for the natural aroma of [[buckwheat]].<ref>{{cite journal
| author=Janes D, Kantar D, Kreft S, Prosen H
| author=Janes D, Kantar D, Kreft S, Prosen H
| title=Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS
| title=Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS
| journal=Food Chemistry
| journal=Food Chemistry
| volume=112
| volume=112
| issue=
| issue=
| pages=120
| pages=120
| date=2008
| date=2008
| doi=10.1016/j.foodchem.2008.05.048
| doi=10.1016/j.foodchem.2008.05.048
}}</ref>
}}</ref>


Revision as of 00:37, 2 November 2015

2-Methoxy-4-vinylphenol
Names
IUPAC name
4-Ethenyl-2-methoxyphenol
Other names
4-Hydroxy-3-methoxystyrene
4-Vinylguaiacol
p-Vinylguaiacol
p-Vinicatechol-o-methyl ether
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.029.183 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 checkY
    Key: YOMSJEATGXXYPX-UHFFFAOYSA-N checkY
  • InChI=1/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3
    Key: YOMSJEATGXXYPX-UHFFFAOYAD
  • Oc1ccc(cc1OC)C=C
Properties
C9H10O2
Molar mass 150.177 g·mol−1
Boiling point 224 °C (435 °F; 497 K)
Hazards
Flash point 113 °C (235 °F; 386 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

2-Methoxy-4-vinylphenol is an aromatic substance used as a flavoring agent.[1] It is one of the compounds responsible for the natural aroma of buckwheat.[2]

Some insects such as Rhynchophorus ferrugineus (Red palm weevil) use this substance for chemical signaling (pheromones).[3]

The aroma of pure substance was described as: apple, spicy, peanut, wine-like or clove and curry.

Ferulic acid is converted by certain strains of yeast, notably strains used in brewing of wheat beers, such as Torulaspora delbrueckii to 2-methoxy-4-vinylphenol which gives beers such as Weissbier and Wit their distinctive "clove" flavor. Saccharomyces cerevisiae (dry brewer's yeast) and Pseudomonas fluorescens are also able to convert trans-ferulic acid into 2-methoxy-4-vinylphenol.[4]

References

  1. ^ 2-METHOXY-4-VINYLPHENOL, Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives
  2. ^ Janes D, Kantar D, Kreft S, Prosen H (2008). "Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS". Food Chemistry. 112: 120. doi:10.1016/j.foodchem.2008.05.048.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Semiochemical - 2-methoxy-4-vinylphenol, Pherobase.com
  4. ^ Huang, Z.; Dostal, L.; Rosazza, J. P. (1993). "Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens". Applied and environmental microbiology. 59 (7): 2244–2250. PMC 182264. PMID 8395165.
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