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4-hydroxycinnamate Decarboxylase
4-Hydroxycinnamate decarboxylase is an enzyme that uses ''p''-coumaric acid to produce 4-ethylphenol. ''p''-Coumaric acid is the precursor of 4-ethylphenol produced by the yeast ''Saccharomyces'' and '' Brettanomyces'' in wine. The yeast converts this to 4-vinylphenol via the enzyme cinnamate decarboxylase. 4-Hydroxycinnamate decarboxylase can also be induced in bacteria species such as ''Klebsiella oxytoca'' and works also with p-coumaric acid analogs such as caffeic acid, ferulic acid and E-2,4-dihydroxycinnamic acid. References See also * Wine chemistry Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4. The chemistry of wine and its resultant quality depend on achieving a balance between three aspects of the berries used to make the wine: their sugar ... {{enzyme-stub Hydroxycinnamic acids metabolism EC 4.1.1 ...
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Enzyme
Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. Almost all metabolic processes in the cell need enzyme catalysis in order to occur at rates fast enough to sustain life. Metabolic pathways depend upon enzymes to catalyze individual steps. The study of enzymes is called ''enzymology'' and the field of pseudoenzyme analysis recognizes that during evolution, some enzymes have lost the ability to carry out biological catalysis, which is often reflected in their amino acid sequences and unusual 'pseudocatalytic' properties. Enzymes are known to catalyze more than 5,000 biochemical reaction types. Other biocatalysts are catalytic RNA molecules, called ribozymes. Enzymes' specificity comes from their unique three-dimensional structures. Like all catalysts, enzymes increase the reaction ra ...
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4-ethylphenol
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. Natural occurrences In wine and beer, 4-EP is produced by the yeast ''Brettanomyces''. At concentrations greater than 140 μg/L (typical sensory threshold) it gives the wine aromas described as ''barnyard'', ''medicinal'', ''band-aids'', and ''mousy''. In certain Belgian beer styles, a high 4-EP level may be desirable; however, very high levels of the compound in wine can render it undrinkable. The level of 4-EP is roughly proportional to ''Brettanomyces'' concentration and activity, and can therefore be used as an indicator of the yeast's presence. There are significant differences between strains of ''Brettanomyces'' in their ability to produce 4-EP. 4-EP is also a component of castoreum, the e ...
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Yeast (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.Jeff Cox ''"From Vines to Wines: The Complete Guide to Growing Grapes and Making Your Own Wine"'' pp. 133–36 Storey Publishing 1999 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.D. Bird ''"Understanding Wine Technology"'' pp. 67–73 DBQA Publishing 2005 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 unintentiona ...
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Saccharomyces
''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. It is known as the brewer's yeast or baker's yeast. 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 cerevisiae'' var. ''boulardii'', used in medicine. Morphology Colonies of ''Saccharomyces'' grow rapidly and mature in three days. They are flat, smooth, moist, glistening or dull, and cream in color. The inability to use nitrate and ability to ferment various carbohydrates are typical characteristics of ''Sacc ...
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Brettanomyces
''Brettanomyces'' is a non-spore forming genus of yeast in the family Saccharomycetaceae, and is often colloquially referred to as "Brett". The genus name ''Dekkera'' is used interchangeably with ''Brettanomyces'', as it describes the teleomorph or spore forming form of the yeast, but is considered deprecated under the one fungus, one name change. The cellular morphology of the yeast can vary from ovoid to long "sausage" shaped cells. The yeast is acidogenic, and when grown on glucose rich media under aerobic conditions, produces large amounts of acetic acid. ''Brettanomyces'' is important to both the brewing and wine industries due to the sensory compounds it produces. In the wild, ''Brettanomyces'' lives on the skins of fruit. History In 1889, Seyffert of the Kalinkin Brewery in St. Petersburg was the first to isolate a "''Torula''" from English beer which produced the typical "English" taste in lager beer, and in 1899 JW Tullo at Guinness described two types of "secondary y ...
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Klebsiella Oxytoca
''Klebsiella oxytoca'' is a Gram-negative, rod-shaped bacterium that is closely related to ''K. pneumoniae'', from which it is distinguished by being indole-positive; it also has slightly different growth characteristics in that it is able to grow on melezitose, but not 3-hydroxybutyrate. It was first described in 1886 when it was isolated from sour milk and named ''Bacillus oxytocus perniciosus'' (from Greek ''oxus'' 'sour' + ''-tokos'' 'producing'). ''Klebsiella oxytoca'' is characterized by negative methyl red, positive VP, positive citrate, urea and TSI gas production, is AA, and negative for TSI sulfide, DNAse, growth on sulfide-indole motility medium and the phenylalanine deaminase test. It is a diazotroph, able to colonise plant hosts and fix atmospheric nitrogen into a form which the plant can use. Association of ''K. oxytoca'' with the barley rhizosphere during an entire vegetative period has been demonstrated. The bacteria adhere strongly to root hairs, and less stron ...
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Caffeic Acid
Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues. Natural occurrences Caffeic acid can be found in the bark of ''Eucalyptus globulus'' the barley grain ''Hordeum vulgare'' and the herb ''Dipsacus asperoides''. It can also be found in the freshwater fern ''Salvinia molesta'' and in the mushroom ''Phellinus linteus''. Occurrences in food Free caffeic acid can be found in a variety of beverages, including brewed coffee at 0.13 mg per 100 ml and red wine at 2 mg per 100 ml. It is found at relatively high levels in herbs of the mint family, especially thyme, sage and spearmint (at about 20 mg per 100 g), and in spices, such as Ceylon cinnamon and star anise (at about 22 mg per 100  ...
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Ferulic Acid
Ferulic acid is a hydroxycinnamic acid, 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. Occurrence in nature As a building block of lignocelluloses, such as pectin and lignin, ferulic acid is ubiquitous in the plant kingdom, including a number of vegetable sources. It occurs in particularly high concentrations in popcorn and bamboo shoots. It is a major metabolite of chlorogenic acids in humans along with caffeic and isoferulic acid, and is absorbed in the small intestine, whereas other metabolites such as dihydroferulic acid, feruloylglycine and dihydroferulic acid sulfate are produced from chlorogenic acid in the large intestine by the action of gut flora. In cereals, f ...
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2,4-dihydroxycinnamic Acid
Umbellic acid (2,4-dihydroxycinnamic acid) is a hydroxycinnamic acid. It is an isomer of caffeic acid. It is a precursor in the umbelliferone biosynthesis pathway. Umbelliferone is a phenylpropanoid and as such is synthesized from L-phenylalanine, which in turn is produced via the shikimate pathway. Phenylalanine is lysated into cinnamic acid, followed by hydroxylation by cinnamate 4-hydroxylase to yield 4-coumaric acid. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid followed by a bond rotation of the unsaturated bond adjacent to the carboxylic acid group. Finally an intramolecular attack from the hydroxyl group of C2' to the carboxylic acid group closes the ring and forms the lactone umbelliferone. :  \xrightarrow  \xrightarrow  \xrightarrow  \longrightarrow  The enzyme 4-hydroxycinnamate decarboxylase, induced in bacteria species such as ''Klebsiella oxytoca ''Kle ...
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Wine Chemistry
Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4. The chemistry of wine and its resultant quality depend on achieving a balance between three aspects of the berries used to make the wine: their sugar content, acidity and the presence of secondary compounds. Vines store sugar in grapes through photosynthesis, and acids break down as grapes ripen. Secondary compounds are also stored in the course of the season. Anthocyanins give grapes a red color and protection against ultraviolet light. Tannins add bitterness and astringency which acts to defend vines against pests and grazing animals. Environmental factors such as soil, rainfall and fog affect flavor in ways that can be described collectively as "character" or the French term “terroir”. As climate change disrupts long-established patterns of temperature and precipitation in wine-growing regions and causes more extreme weather events, the rate at which sugars, acids and seconda ...
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