2-Methoxy-4-vinylphenol

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 (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 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 (brewer'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: 120–124. 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. PMC 182264. PMID 8395165.

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[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. PMC 182264. PMID 8395165.