2-Methoxy-4-vinylphenol

Last updated
2-Methoxy-4-vinylphenol
2-methoxy-4-vinylphenol.png
Names
Preferred IUPAC name
4-Ethenyl-2-methoxyphenol
Other names
4-Hydroxy-3-methoxystyrene
4-Vinylguaiacol
p-Vinylguaiacol
p-Vinicatechol-o-methyl ether
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.029.183 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3 Yes check.svgY
    Key: YOMSJEATGXXYPX-UHFFFAOYSA-N Yes check.svgY
  • 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
C9H10O2
Molar mass 150.177 g·mol−1
Boiling point 269.35 °C (516.83 °F; 542.50 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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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]

Related Research Articles

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Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constitute 1% of all described fungal species.

<span class="mw-page-title-main">Wheat beer</span> Beer brewed in part with wheat

Wheat beer is a top-fermented beer which is brewed with a large proportion of wheat relative to the amount of malted barley. The two main varieties are German Weizenbier and Belgian witbier; other types include Lambic, Berliner Weisse, and Gose.

In cooking, a leavening agent or raising agent, also called a leaven or leavener, is any one of a number of substances used in doughs and batters that cause a foaming action that lightens and softens the mixture. An alternative or supplement to leavening agents is mechanical action by which air is incorporated. Leavening agents can be biological or synthetic chemical compounds. The gas produced is often carbon dioxide, or occasionally hydrogen.

<i>Saccharomyces cerevisiae</i> Species of yeast

Saccharomyces cerevisiae is a species of yeast. The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have been originally isolated from the skin of grapes. It is one of the most intensively studied eukaryotic model organisms in molecular and cell biology, much like Escherichia coli as the model bacterium. It is the microorganism which causes many common types of fermentation. S. cerevisiae cells are round to ovoid, 5–10 μm in diameter. It reproduces by budding.

<i>Pseudomonas fluorescens</i> Species of bacterium

Pseudomonas fluorescens is a common Gram-negative, rod-shaped bacterium. It belongs to the Pseudomonas genus; 16S rRNA analysis as well as phylogenomic analysis has placed P. fluorescens in the P. fluorescens group within the genus, to which it lends its name.

<i>Saccharomyces</i> Genus of fungi

Saccharomyces is a genus of fungi that includes many species of yeasts. Saccharomyces is from Greek σάκχαρον (sugar) and μύκης (fungus) and means sugar fungus. Many members of this genus are considered very important in food production where they are known as brewer's yeast, baker's yeast and sourdough starter among others. They are unicellular and saprotrophic fungi. One example is Saccharomyces cerevisiae, which is used in making bread, wine, and beer, and for human and animal health. Other members of this genus include the wild yeast Saccharomyces paradoxus that is the closest relative to S. cerevisiae, Saccharomyces bayanus, used in making wine, and Saccharomyces cerevisiaevar. boulardii, used in medicine.

<span class="mw-page-title-main">Ferulic acid</span> Chemical compound

Ferulic acid is a hydroxycinnamic acid derivative and a phenolic compound. It is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans. Salts and esters derived from ferulic acid are called ferulates.

Ethylphenol (4-EP) is an organic compound with the formula C2H5C6H4OH. It is one of three isomeric ethylphenols. A white solid, it occurs as an impurity in xylenols and as such is used in the production of some commercial phenolic resins. It is also a precursor to 4-vinylphenol.

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Saccharomyces boulardii is a tropical yeast first isolated from lychee and mangosteen fruit peel in 1923 by French scientist Henri Boulard. Although early reports claimed distinct taxonomic, metabolic, and genetic properties, S. boulardii is genetically a grouping of S. cerevisiae strains, sharing >99% genomic relatedness, giving the synonym S. cerevisiae var. boulardii.

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The process of fermentation in winemaking turns grape juice into an alcoholic beverage. During fermentation, yeasts transform sugars present in the juice into ethanol and carbon dioxide. In winemaking, the temperature and speed of fermentation are important considerations as well as the levels of oxygen present in the must at the start of the fermentation. The risk of stuck fermentation and the development of several wine faults can also occur during this stage, which can last anywhere from 5 to 14 days for primary fermentation and potentially another 5 to 10 days for a secondary fermentation. Fermentation may be done in stainless steel tanks, which is common with many white wines like Riesling, in an open wooden vat, inside a wine barrel and inside the wine bottle itself as in the production of many sparkling wines.

<span class="mw-page-title-main">Phenylacetaldehyde</span> Chemical compound

Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.

4-Vinylphenol is an organic compound with the formula C2H3C6H4OH. It is the most studied of the three isomeric vinylphenols. It is a white volatile solid.

<span class="mw-page-title-main">Yeast in winemaking</span> Yeasts used for alcoholic fermentation of wine

The role of yeast in winemaking is the most important element that distinguishes wine from fruit juice. In the absence of oxygen, yeast converts the sugars of the fruit into alcohol and carbon dioxide through the process of fermentation. The more sugars in the grapes, the higher the potential alcohol level of the wine if the yeast are allowed to carry out fermentation to dryness. Sometimes winemakers will stop fermentation early in order to leave some residual sugars and sweetness in the wine such as with dessert wines. This can be achieved by dropping fermentation temperatures to the point where the yeast are inactive, sterile filtering the wine to remove the yeast or fortification with brandy or neutral spirits to kill off the yeast cells. If fermentation is unintentionally stopped, such as when the yeasts become exhausted of available nutrients and the wine has not yet reached dryness, this is considered a stuck fermentation.

4-Hydroxycinnamate decarboxylase is an enzyme that uses p-coumaric acid to produce 4-ethylphenol.

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Debaryomyces hansenii, also known as Candida famata, is a species of yeast in the family Saccharomycetaceae.

Aerobic fermentation or aerobic glycolysis is a metabolic process by which cells metabolize sugars via fermentation in the presence of oxygen and occurs through the repression of normal respiratory metabolism. Preference of aerobic fermentation over aerobic respiration is referred to as the Crabtree effect in yeast, and is part of the Warburg effect in tumor cells. While aerobic fermentation does not produce adenosine triphosphate (ATP) in high yield, it allows proliferating cells to convert nutrients such as glucose and glutamine more efficiently into biomass by avoiding unnecessary catabolic oxidation of such nutrients into carbon dioxide, preserving carbon-carbon bonds and promoting anabolism.

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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. Bibcode:1993ApEnM..59.2244H. doi:10.1128/aem.59.7.2244-2250.1993. PMC   182264 . PMID   8395165.