Names | |
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IUPAC name 2-[(E)-3-[3-[2-[(4-amino-4-carboxybutanoyl)amino]-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-4,5-dihydroxyphenyl]prop-2-enoyl]oxy-3-hydroxybutanedioic acid | |
Other names GRP GRP1 2-S-Glutathionyl caftaric acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
PubChem CID | |
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Properties | |
C23H27N3O15S | |
Molar mass | 617.54 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
The grape reaction product (GRP, GRP1 or 2-S-glutathionyl caftaric acid [1] ) is a phenolic compound explaining the disappearance of caftaric acid from grape must during processing. [2] It is also found in aged red wines. [3] Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts, [4] especially in white wine production. The product can be recreated in model solutions. [5] [6]
Determining its concentration in wine is possible by mass spectrometry. [7]
S-Glutathionyl caftaric acid is itself oxidizable. [8] It is not a substrate for grape polyphenol oxidase, but laccase from Botrytis cinerea can use it to form GRP2. [9]
Other related molecules are trans-caffeoyltartrate derivatives like GRP o-quinone [10] and 2,5-di-S-glutathionyl cafteoyl tartrate (GRP2) [11] or adducts with anthocyanidins. [12]
Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.
Browning is the process of food turning brown due to the chemical reactions that take place within. The process of browning is one of the chemical reactions that take place in food chemistry and represents an interesting research topic regarding health, nutrition, and food technology. Though there are many different ways food chemically changes over time, browning in particular falls into two main categories: enzymatic versus non-enzymatic browning processes.
A winepress is a device used to extract juice from crushed grapes during winemaking. There are a number of different styles of presses that are used by wine makers but their overall functionality is the same. Each style of press exerts controlled pressure in order to free the juice from the fruit. The pressure must be controlled, especially with grapes, in order to avoid crushing the seeds and releasing a great deal of undesirable tannins into the wine. Wine was being made at least as long ago as 4000 BC; in 2011, a winepress was unearthed in Armenia with red wine dated 6,000 years old.
Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It is a polyphenol. It is a yellow solid. Structurally, it is classified as a hydroxycinnamic acid. The molecule consists of both phenolic and acrylic functional groups. It is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues. It is unrelated to caffeine.
Hydroxycinnamic acids (hydroxycinnamates) are a class of aromatic acids or phenylpropanoids having a C6–C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid.
Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of condensed tannins.
Laccases are multicopper oxidases found in plants, fungi, and bacteria. Laccases oxidize a variety of phenolic substrates, performing one-electron oxidations, leading to crosslinking. For example, laccases play a role in the formation of lignin by promoting the oxidative coupling of monolignols, a family of naturally occurring phenols. Other laccases, such as those produced by the fungus Pleurotus ostreatus, play a role in the degradation of lignin, and can therefore be classed as lignin-modifying enzymes. Other laccases produced by fungi can facilitate the biosynthesis of melanin pigments. Laccases catalyze ring cleavage of aromatic compounds.
Procyanidins are members of the proanthocyanidin class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.
The Folin–Ciocâlteu reagent (FCR) or Folin's phenol reagent or Folin–Denis reagent, is a mixture of phosphomolybdate and phosphotungstate used for the colorimetric in vitro assay of phenolic and polyphenolic antioxidants, also called the gallic acid equivalence method (GAE). It is named after Otto Folin, Vintilă Ciocâlteu, and Willey Glover Denis. The Folin-Denis reagent is prepared by mixing sodium tungstate and phosphomolybdic acid in phosphoric acid. The Folin–Ciocalteu reagent is just a modification of the Folin-Denis reagent. The modification consisted of the addition of lithium sulfate and bromine to the phosphotungstic-phosphomolybdic reagent.
Polyphenol oxidase, an enzyme involved in fruit browning, is a tetramer that contains four atoms of copper per molecule.
Sugars in wine are at the heart of what makes winemaking possible. During the process of fermentation, sugars from wine grapes are broken down and converted by yeast into alcohol (ethanol) and carbon dioxide. Grapes accumulate sugars as they grow on the grapevine through the translocation of sucrose molecules that are produced by photosynthesis from the leaves. During ripening the sucrose molecules are hydrolyzed (separated) by the enzyme invertase into glucose and fructose. By the time of harvest, between 15 and 25% of the grape will be composed of simple sugars. Both glucose and fructose are six-carbon sugars but three-, four-, five- and seven-carbon sugars are also present in the grape. Not all sugars are fermentable, with sugars like the five-carbon arabinose, rhamnose and xylose still being present in the wine after fermentation. Very high sugar content will effectively kill the yeast once a certain (high) alcohol content is reached. For these reasons, no wine is ever fermented completely "dry". Sugar's role in dictating the final alcohol content of the wine sometimes encourages winemakers to add sugar during winemaking in a process known as chaptalization solely in order to boost the alcohol content – chaptalization does not increase the sweetness of a wine.
Phenolic compounds—natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.
The color of wine is one of the most easily recognizable characteristics of wines. Color is also an element in wine tasting since heavy wines generally have a deeper color. The accessory traditionally used to judge the wine color was the tastevin, a shallow cup allowing one to see the color of the liquid in the dim light of a cellar. The color is an element in the classification of wines.
Caftaric acid is a non-flavonoid phenolic compound.
Oenin is an anthocyanin. It is the 3-glucoside of malvidin. It is one of the red pigments found in the skin of purple grapes and in wine.
The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes or during controlled oxygenation processes during the aging of wine. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins, oxovitisins and pyranoanthocyanin dimers; their general structure includes an additional ring that may have different substituents linked directly at C-10.
Coutaric acid is a hydroxycinnamoyltartaric acid found in wine, pomace and grape. It is an ester formed from coumaric acid and tartaric acid.
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.
Flash release (FR) is a technique used in wine pressing. The technique allows for a better extraction of phenolic compounds and wine polysaccharides.
Malvidin glucoside-ethyl-catechin is a flavanol-anthocyanin adduct. Flavanol-anthocyanin adducts are formed during wine ageing through reactions between anthocyanins and tannins present in grape, with yeast metabolites such as acetaldehyde. Acetaldehyde-induced reactions yield ethyl-linked species such as malvidin glucoside-ethyl-catechin.