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1 References  














2-Methoxy-4-vinylphenol






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From Wikipedia, the free encyclopedia
 

(Redirected from 4-vinyl guaiacol)

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

3D model (JSmol)

ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.029.183 Edit this at Wikidata
KEGG

PubChem CID

UNII

CompTox Dashboard (EPA)

  • InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 checkY

    Key: YOMSJEATGXXYPX-UHFFFAOYSA-N checkY

  • InChI=1/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3

    Key: YOMSJEATGXXYPX-UHFFFAOYAD

  • 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).

☒N verify (what is checkY☒N ?)

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

[edit]
  1. ^ 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.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=2-Methoxy-4-vinylphenol&oldid=1136242560"

    Categories: 
    O-methylated natural phenols
    Insect pheromones
    Vanilloids
    Vinyl compounds
    Hidden categories: 
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    ECHA InfoCard ID from Wikidata
    Articles containing unverified chemical infoboxes
    Chembox image size set
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