Petunidin-3-O-glucoside

Last updated
Petunidin-3-O-glucoside
Petunidin-3-O-glucoside.svg
Names
IUPAC name
(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
Petunidin-3-glucoside
Petunidin 3-O-glucoside
Petunidin 3-O-β-glucopyranoside
Identifiers
  • 6988-81-4(chloride) Yes check.svgY
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C22H22O12/c1-31-14-3-8(2-12(26)17(14)27)21-15(6-10-11(25)4-9(24)5-13(10)32-21)33-22-20(30)19(29)18(28)16(7-23)34-22/h2-6,16,18-20,22-23,28-30H,7H2,1H3,(H3-,24,25,26,27)/p+1/t16-,18-,19+,20-,22-/m1/s1
    Key: CCQDWIRWKWIUKK-QKYBYQKWSA-O
  • COC1=CC(=CC(=C1O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O
Properties
C
22
H
23
O+
12

C22H23O12Cl (chloride)
Molar mass 479.41 g/mol, 514.86 g/mol (chloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Petunidin-3-O-glucoside is anthocyanin. It is found in fruits and berries, in red Vitis vinifera grapes and red wine. [1]

See also

Related Research Articles

<i>Vitis vinifera</i> Species of flowering plant in the grape vine family Vitaceae

Vitis vinifera, the common grape vine, is a species of flowering plant, native to the Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern Iran. There are currently between 5,000 and 10,000 varieties of Vitis vinifera grapes though only a few are of commercial significance for wine and table grape production.

Cyanidin anthocyanidin pigment in flowering plant plant petals and fruits

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin. It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry. It can also be found in other fruits such as apples and plums, and in red cabbage and red onion. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin. Cyanidin has been found to be a potent sirtuin 6 (SIRT6) activator.

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.

Petunidin Chemical compound

Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many redberries including chokeberries, Saskatoon berries or different species of grape, and also part of the pigments responsible for the petal colors in many flowers. This pigment gives the Indigo Rose tomatoes the majority of their deep purple color when the fruits are exposed to sunlight. The name of the molecule itself is derived from the word Petunia.

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.

Astragalin Chemical compound

Astragalin is a chemical compound. It can be isolated from Phytolacca americana or in the methanolic extract of fronds of the fern Phegopteris connectilis. It is also found in wine.

Caftaric acid Chemical compound

Caftaric acid is a non-flavonoid phenolic compound.

Oenin Chemical 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.

Chrysanthemin Chemical compound

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin.

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.

Syringetin Chemical compound

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape, in Lysimachia congestiflora and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

Laricitrin Chemical compound

Laricitrin is an O-methylated flavonol, a type of flavonoid. It is found in red grape and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

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.

Delphinidin-3-<i>O</i>-(6-<i>p</i>-coumaroyl)glucoside Chemical compound

Delphinidin 3-O-(6-p-coumaroyl)glucoside is a p-coumaroylated anthocyanin. It can be found in some red Vitis vinifera grape cultivars and in red wine.

Peonidin-3-<i>O</i>-glucoside Chemical compound

Peonidin-3-O-glucoside is anthocyanin. It is found in fruits and berries, in red Vitis vinifera grapes and red wine, in red onions and in purple corn. It is dark red to purple in colour.

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.

Malvidin-3-<i>O</i>-(6-<i>p</i>-coumaroyl)glucoside Chemical compound

Malvidin-3-O-(6-p-coumaroyl)glucoside is a p-coumaroylated anthocyanin found in grape and wine. There are two forms with the cis and trans isomers of p-coumaric acid. It is a cation.

<i>p</i>-Coumaroylated anthocyanin

p-Coumaroylated anthocyanins are a type of anthocyanins with a p-coumaric acid unit linked with a sugar to an anthocyanidin aglycone. 3-(6-p-Coumaroyl)glucosides are found in grape and wine. Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside is found in dark opal basil. Red leaves of Perilla frutescens also accumulate cyanidin 3-(6-O-p-coumaroyl-β-D-glucoside)-5-(6-O-malonyl-β-D-glucoside).

References

  1. Petunidin 3-O-glucoside on www.phenol-explorer.eu Archived 2013-02-13 at archive.today