2-Methoxy-4-vinylphenol

2-Methoxy-4-vinylphenol
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 Y
PubChem	332
ChemSpider	325 Y
UNII	DA069CTH0O Y
DrugBank	DB03514
KEGG	C17883 Y
Jmol-3D images	Image 1
SMILES Oc1ccc(cc1OC)C=C
InChI InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 Y Key: YOMSJEATGXXYPX-UHFFFAOYSA-N Y InChI=1/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 Key: YOMSJEATGXXYPX-UHFFFAOYAD
Properties
Molecular formula	C9H10O2
Molar mass	150.17 g mol−1
Exact mass	150.06808 u
Boiling point	224 °C, 497 K, 435 °F
Hazards
Flash point	113 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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

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. 
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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=182264.  edit