Vitisin B (pyranoanthocyanin)

Last updated
Vitisin B
Vitisin B.svg
Names
Preferred IUPAC name
8-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4-pyrano[4,3,2-de][1]benzopyran-1-ylium
Other names
Pyranomalvidin-3-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C25H24O12/c1-32-15-5-10(6-16(33-2)19(15)28)23-24(37-25-22(31)21(30)20(29)17(9-26)36-25)12-3-4-34-13-7-11(27)8-14(35-23)18(12)13/h3-8,17,20-22,25-26,29-31H,9H2,1-2H3,(H-,27,28)/p+1/t17-,20-,21+,22-,25+/m1/s1 X mark.svgN
    Key: ZFFLAEFKTXRRFR-FHBCLOHASA-O X mark.svgN
  • InChI=1/C25H24O12/c1-32-15-5-10(6-16(33-2)19(15)28)23-24(37-25-22(31)21(30)20(29)17(9-26)36-25)12-3-4-34-13-7-11(27)8-14(35-23)18(12)13/h3-8,17,20-22,25-26,29-31H,9H2,1-2H3,(H-,27,28)/p+1/t17-,20-,21+,22-,25+/m1/s1
    Key: ZFFLAEFKTXRRFR-IPEXBSMVBT
  • COc1cc(cc(c1O)OC)c2c(c3c4c([o+]2)cc(cc4OC=C3)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
Properties
C25H25O12+
Molar mass 517.45 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Vitisin B is a natural phenol found in red wines. [1] [2] It is a pyranoanthocyanin. [3] [4] [5]

See also

Related Research Articles

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.

Polyphenol Class of chemical compounds

Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

Tropolone Chemical compound

Tropolone is an organic compound with the chemical formula C7H5(OH)O. It is a pale yellow solid that is soluble in organic solvents. The compound has been of interest to research chemists because of its unusual electronic structure and its role as a ligand precursor. Although not usually prepared from tropone, it can be viewed as its derivative with a hydroxyl group in the 2-position.

Phenolic content in wine Wine chemistry

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.

Procyanidin C2 Chemical compound

Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin.

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.

Grandinin Chemical compound

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak and European red oak. It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

Syringic acid Chemical compound

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

Xanthonoid Class of phenolic chemical compounds

A xanthonoid is a chemical natural phenolic compound formed from the xanthone backbone. Many members of the Clusiaceae contain xanthonoids.

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.

Hopeaphenol Chemical compound

Hopeaphenol is a stilbenoid. It is a resveratrol tetramer. It has been first isolated from Dipterocarpaceae like Shorea ovalis. It has also been isolated from wines from North Africa.

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. 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.

Castavinol

Castavinols are natural phenolic compounds found in red wines. These molecules are colorless and are derived from anthocyanin pigments. Thus their formation leads to a wine color loss.

Pinotin A Chemical compound

Pinotin A is a pinotin, a type of pyranoanthocyanins and a class of phenolic compounds found in red 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.

References

  1. Brazilian red wines made from the hybrid grape cultivar Isabel: Phenolic composition and antioxidant capacity. Suzana Lucy Nixdorf and Isidro Hermosín-Gutiérrez, Analytica Chimica Acta, Volume 659, Issues 1-2, 5 February 2010, Pages 208-215, doi : 10.1016/j.aca.2009.11.058
  2. Formation of the highly stable pyranoanthocyanins (vitisins A and B) in red wines by the addition of pyruvic acid and acetaldehyde. A. Morata, F. Calderón, M.C. González, M.C. Gómez-Cordovés and J.A. Suárez, Food Chemistry, Volume 100, Issue 3, 2007, Pages 1144-1152, doi : 10.1016/j.foodchem.2005.11.024
  3. A novel synthetic pathway to vitisin B compounds. Joana Oliveira, Victor de Freitas and Nuno Mateus, Tetrahedron Letters, Volume 50, Issue 27, 8 July 2009, Pages 3933-3935, doi : 10.1016/j.tetlet.2009.04.072
  4. Charge equilibria and pK values of 5-carboxypyranomalvidin-3-glucoside (vitisin A) by electrophoresis and absorption spectroscopy. Robert E. Asenstorfer and Graham P. Jones, Tetrahedron, Volume 63, Issue 22, 28 May 2007, Pages 4788-4792, doi : 10.1016/j.tet.2007.03.052
  5. Effect of acetaldehyde and several acids on the formation of vitisin A in model wine anthocyanin and colour evolution. Romero C. and Bakker J., International journal of food science & technology, 2000, vol. 35, no. 1, pp. 129-140, INIST : 1283952