Pinotin A

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Pinotin A
Pinotin A.svg
Identifiers
  • 663910-41-6 X mark.svgN
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C31H28O14/c1-40-21-6-13(7-22(41-2)25(21)36)29-30(45-31-28(39)27(38)26(37)23(11-32)44-31)15-10-18(12-3-4-16(34)17(35)5-12)42-19-8-14(33)9-20(43-29)24(15)19/h3-10,23,26-28,31-32,37-39H,11H2,1-2H3,(H3-,33,34,35,36)/p+1/t23-,26-,27+,28-,31+/m1/s1
    Key: RFTHDRVOYDHSOC-BGXVWEPQSA-O
  • COc1cc(cc(c1O)OC)c2c(c3c4c([o+]2)cc(cc4OC(=C3)c5ccc(c(c5)O)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
Properties
C31H29O14+
Molar mass 625.55 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Pinotin A is a pinotin, a type of pyranoanthocyanins and a class of phenolic compounds found in red wine. [1] [2]

Contents

See also

Related Research Articles

Resveratrol Chemical compound

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts.

Hydroxytyrosol Chemical compound

Hydroxytyrosol is a phenylethanoid, a type of phenolic phytochemical with antioxidant properties in vitro. In nature, hydroxytyrosol is mainly found in olives, olive leaves, and olive oil in the form of its elenolic acid ester, oleuropein. It is a constituent of red and white wines.

Flavonols Class of plant and fungus secondary metabolites

Flavonols are a class of flavonoids that have the 3-hydroxyflavone backbone. Their diversity stems from the different positions of the phenolic -OH groups. They are distinct from flavanols such as catechin, another class of flavonoids.

Anthocyanin

Anthocyanins are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical compound that gives flowers a blue color for the first time in his treatise “Die Farben der Blüthen”. Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

Phenolic content in wine

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which 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.

Wine color

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.

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.

Syringic acid Chemical compound

Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.

Naturally occurring phenols Group of chemical compounds

In biochemistry, naturally occurring phenols refers to phenol functional group that is found in natural products. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

Grape reaction product Chemical compound

The grape reaction product is a phenolic compound explaining the disappearance of caftaric acid from grape must during processing. It is also found in aged red wines. Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts, especially in white wine production. The product can be recreated in model solutions.

Vitisin A (pyranoanthocyanin) Chemical compound

Vitisin A is a natural phenol found in red wines. It is a pyranoanthocyanin.

Vitisin B (pyranoanthocyanin) Chemical compound

Vitisin B is a natural phenol found in red wines. It is a pyranoanthocyanin.

Pinotin

Pinotins are a type of pyranoanthocyanins, a class of phenolic compounds found in red wine. One such compound is pinotin A.

Wine chemistry

Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4.

Ethyl protocatechuate Chemical compound

Ethyl protocatechuate is a phenolic compound. It can be found in the peanut seed testa. It is also present in wine. It is the ethylic ester of protocatechuic acid.

Portosin

Portosins are vinylpyranoanthocyanins, a type of blueish phenolic pigments, found in aged port wine.

Malvidin glucoside-ethyl-catechin Chemical compound

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.

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.

Cyanidin-3,5-<i>O</i>-diglucoside Chemical compound

Cyanidin-3,5-O-diglucoside, also known as cyanin, is an anthocyanin. It is the 3,5-O-diglucoside of cyanidin.

Pelargonin Chemical compound

Pelargonin is an anthocyanin. It is the 3,5-O-diglucoside of pelargonidin.

References

  1. Investigations on Anthocyanins in Wines from Vitis vinifera cv. Pinotage: Factors Influencing the Formation of Pinotin A and Its Correlation with Wine Age. Schwarz Michael, Hofmann Glenn and Winterhalter Peter, J. Agric. Food Chem., 2004, 52 (3): 498–504. doi : 10.1021/jf035034f
  2. Variation of pyranoanthocyanins in red wines of different varieties and vintages and the impact of pinotin A addition on their color parameters. Michael Rentzsch, Fabian Weber, Dominik Durner, Ulrich Fischer and Peter Winterhalter, European Food Research and Technology, Volume 229, Number 4, pp. 689-696, doi : 10.1007/s00217-009-1102-4
  3. "Showing dietary polyphenol Pinotin a aglycone - Phenol-Explorer".