2-Methoxy-4-vinylphenol

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
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	269.35 °C (516.83 °F; 542.50 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). verify (what is ?) Infobox references

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

^ 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: 120–124. doi:10.1016/j.foodchem.2008.05.048.
^ Semiochemical - 2-methoxy-4-vinylphenol, Pherobase.com
^ 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.

[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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