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
ChEBI	CHEBI:42438
ChemSpider	325
DrugBank	DB03514
Jmol interactive 3D	Image
KEGG	C17883
PubChem	332
UNII	DA069CTH0O
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	150.18 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).
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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 (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: 120–124. 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.