2-Methoxy-4-vinylphenol: Difference between revisions

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| ImageFile = 2-methoxy-4-vinylphenol.png
| ImageFile = 2-methoxy-4-vinylphenol.png
| ImageSize = 240px
| ImageSize = 240px
| IUPACName = 4-Ethenyl-2-methoxyphenol
| PIN = 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 =
| NFPA-H = | NFPA-F = | NFPA-R =
| FlashPtC = 113
| NFPA-H = | NFPA-F = | NFPA-R =
| FlashPtC = 113
| AutoignitionPtC =
| RPhrases =
| SPhrases =
| AutoignitionC =
}}
}}
}}
}}


'''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
|vauthors=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=120–124
| date=2008
| date=2008
| doi=10.1016/j.foodchem.2008.05.048
| doi=10.1016/j.foodchem.2008.05.048
}}</ref>
}}</ref>


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The aroma of pure substance was described as: apple, spicy, peanut, wine-like or clove and curry.
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 [[Witbier|Wit]] their distinctive "clove" flavor. ''[[Saccharomyces cerevisiae]]'' (dry baker's yeast) and ''[[Pseudomonas fluorescens]]'' are also able to convert [[ferulic acid|''trans''-ferulic acid]] into 2-methoxy-4-vinylphenol.<ref>{{Cite pmid|8395165}}</ref>
[[Ferulic acid]] is converted to 2-methoxy-4-vinylphenol by certain strains of yeast, notably strains used in brewing of wheat beers, such as phenolic (POF+) strains of ''[[Saccharomyces cerevisiae]]'' (brewer's yeast) which gives beers such as [[Weissbier]] and [[Witbier|Wit]] their distinctive spicy "clove" flavor. Various other microbes, including ''[[Torulaspora delbrueckii]]'' and ''[[Pseudomonas fluorescens]]'' are also able to convert [[ferulic acid]] into 2-methoxy-4-vinylphenol.<ref>{{Cite journal
| last1 = Huang | first1 = Z.
| last2 = Dostal | first2 = L.
| last3 = Rosazza | first3 = J. P.
| title = Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens
| journal = Applied and Environmental Microbiology
| volume = 59
| issue = 7
| pages = 2244–2250
| year = 1993
| doi = 10.1128/aem.59.7.2244-2250.1993
| pmid = 8395165
| pmc = 182264
| bibcode = 1993ApEnM..59.2244H
}}</ref>


== References ==
== References ==
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{{DEFAULTSORT:Methoxy-4-vinylphenol, 2-}}
{{DEFAULTSORT:Methoxy-4-vinylphenol, 2-}}
[[Category:O-Methylated phenols]]
[[Category:O-methylated natural phenols]]
[[Category:Insect pheromones]]
[[Category:Insect pheromones]]
[[Category:Vanilloids]]
[[Category:Vanilloids]]
[[Category:Alkenes]]
[[Category:Vinyl compounds]]

Latest revision as of 12:01, 29 January 2023

2-Methoxy-4-vinylphenol
Names
Preferred 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 to 2-methoxy-4-vinylphenol by certain strains of yeast, notably strains used in brewing of wheat beers, such as phenolic (POF+) strains of Saccharomyces cerevisiae (brewer's yeast) which gives beers such as Weissbier and Wit their distinctive spicy "clove" flavor. Various other microbes, including Torulaspora delbrueckii and Pseudomonas fluorescens are also able to convert ferulic acid into 2-methoxy-4-vinylphenol.[4]

References[edit]

  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: 120–124. doi:10.1016/j.foodchem.2008.05.048.
  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. Bibcode:1993ApEnM..59.2244H. doi:10.1128/aem.59.7.2244-2250.1993. PMC 182264. PMID 8395165.
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