2-Methoxy-4-vinylphenol: Difference between revisions

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
CAS Number	7786-61-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:42438 ;
ChemSpider	325 ;
DrugBank	DB03514 ;
ECHA InfoCard	100.029.183
KEGG	C17883 ;
PubChem CID	332;
UNII	DA069CTH0O ;
CompTox Dashboard (EPA)	DTXSID7052529 ;
	InChI InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 Key: YOMSJEATGXXYPX-UHFFFAOYSA-N ; InChI=1/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 Key: YOMSJEATGXXYPX-UHFFFAOYAD;
	SMILES Oc1ccc(cc1OC)C=C;
Properties
Chemical formula	C9H10O2
Molar mass	150.177 g·mol−1
Boiling point	224 °C (435 °F; 497 K)
Hazards
Flash point	113 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 13:17, 29 June 2013

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 Saccharomyces delbrueckii (Torulaspora_delbrueckii), to 4-vinyl guaiacol (2-methoxy-4-vinylphenol) which gives beers such as Weissbier and Wit their distinctive "clove" flavour. Saccharomyces cerevisiae (dry baker's yeast) and Pseudomonas fluorescens are also able to convert trans-ferulic acid into 2-methoxy-4-vinylphenol.^[4]

References

^ 2-METHOXY-4-VINYLPHENOL, Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives
^ 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)
^ Semiochemical - 2-methoxy-4-vinylphenol, Pherobase.com
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 8395165, please use {{cite journal}} with |pmid=8395165 instead.

[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] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 8395165, please use {{cite journal}} with |pmid=8395165 instead.

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@@ Line 69: / Line 69: @@
 {{DEFAULTSORT:Methoxy-4-vinylphenol, 2-}}
-[[Category:Natural phenols]]
+[[Category:O-Methylated natural phenols]]
 [[Category:Insect pheromones]]
 [[Category:Vanilloids]]