2-Methoxy-4-vinylphenol

changed changed 477213842 2-methoxy-4-vinylphenol.png 240px 4-Ethenyl-2-methoxyphenol 4-Hydroxy-3-methoxystyrene4-Vinylguaiacolp-Vinylguaiacolp-Vinicatechol-o-methyl ether correct FDA DA069CTH0O correct kegg C17883 changed EBI 42438 1/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 YOMSJEATGXXYPX-UHFFFAOYAD correct chemspider 1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 correct chemspider YOMSJEATGXXYPX-UHFFFAOYSA-N correct CAS 7786-61-0 332 correct chemspider 325 correct drugbank DB03514 Oc1ccc(cc1OC)C=C 9 10 2 269.35 113 StyreneGuaiacol4-EthylguaiacolCatechol4-Vinylphenol 2-Methoxy-4-vinylphenol (also known as 4-vinyl guaiacol, 4VG) is an aromatic substance used as a flavoring agent.2-METHOXY-4-VINYLPHENOL, Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives It is one of the compounds responsible for the natural aroma of buckwheat.Janes D, Kantar D, Kreft S, Prosen H Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS Food Chemistry 112 120–124 2008 10.1016/j.foodchem.2008.05.048 Some insects such as Rhynchophorus ferrugineus (Red palm weevil) use this substance for chemical signaling (pheromones).Semiochemical - 2-methoxy-4-vinylphenol, Pherobase.com The aroma of pure substance was described as: apple, spicy, peanut, wine-like or clove and curry. Ferulic acid is converted to 4VG by certain strains of yeast, notably strains used in brewing of wheat beers, such as phenolic (POF phenolic off-flavor+) 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 4VG. Huang Z. Dostal L. Rosazza J. P. Microbial transformations of ferulic acid by Saccharomyces cerevisiae and Pseudomonas fluorescens Applied and Environmental Microbiology 59 7 2244–2250 1993 10.1128/aem.59.7.2244-2250.1993 8395165 182264 1993ApEnM..59.2244H Most wild strains of Saccharomyces are POF+. 4VG is considered an off-flavor in more typical types of beer, especially crisp lagers. As a result, most beer/ale strains of Saccharomyces have been selected for the inability to produce 4VG (POF-).Langdon QK Peris D Baker EP Opulente DA Nguyen HV Bond U Gonçalves P Sampaio JP Libkind D Hittinger CT Fermentation innovation through complex hybridization of wild and domesticated yeasts. Nature Ecology & Evolution November 2019 3 11 1576–1586 10.1038/s41559-019-0998-8 31636426 7295394 2019NatEE...3.1576L See also Arene substitution pattern, for 4- vs. p-(para-) and 2- vs. o-(ortho-) Ferulic acid decarboxylase Methoxy group Vinyl group, also known as ethenyl group References Category:O-methylated natural phenols Category:Insect pheromones Category:Vanilloids Category:Vinyl compounds