Oenin

Last updated
Oenin
Malvidin-3-glucoside.svg
Names
IUPAC name
(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
Enin
Malvidin-3-glucoside
Malvidin 3-O-glucoside
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.027.847
PubChem CID
UNII
Properties
C23H25O12+, C23H25ClO12 (chloride)
Molar mass 493.43 g/mol, 528.89 g/mol (chloride)
Appearancedark brown powder (chloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
UV visible spectrum of malvidin 3-O-glucoside. MalvidinG UV visible spectrum.PNG
UV visible spectrum of malvidin 3-O-glucoside.

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 [1] and in wine. [2]

Color stabilization of malvidin 3-glucoside at a higher pH can be explained by self-aggregation of the flavylium cation and copigmentation with the Z-chalcone form. [3] In the presence of procyanidin C2, the red color of oenin appears more stable. However, the HPLC chromatogram shows a decrease in the amplitude of the peaks of oenin and procyanidin C2. Concomitantly, a new peak appears with a maximal absorption in the red region. This newly formed pigment probably comes from the condensation of oenin and procyanidin C2. [4]

Malvidin 3-glucoside alone is not oxidized in the presence of grape polyphenol oxidase, whereas it is degraded in the presence of a crude grape PPO extract and of caftaric acid forming anthocyanidin-caftaric acid adducts. [5]

See also

Related Research Articles

Anthocyanidin chemical compound

Anthocyanidins are common plant pigments, the sugar-free counterparts of anthocyanins. They are based on the flavylium cation, an oxonium ion, with various groups substituted for its hydrogen atoms. They generally change color from red through purple, blue, and bluish green as a function of pH.

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

Vitis vinifera, the common grape vine, is a species of Vitis, 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 chemical compound

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. In a recent study, cyanidin was found to be a potent sirtuin 6 (SIRT6) activator.

Proanthocyanidins are a class of polyphenols found in a variety of plants such as blueberry. 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 tannins.

Malvin chemical compound

Malvin is a naturally occurring chemical of the anthocyanin family.

Malvidin chemical compound

Malvidin is an O-methylated anthocyanidin, the 3',5'-methoxy derivative of delphinidin. As a primary plant pigment, its glycosides are highly abundant in nature.

Procyanidin group of chemical 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.

Anthocyanin class of chemical compounds

Anthocyanins are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue or black. 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.

Caftaric acid chemical compound

Caftaric acid is a non-flavonoid phenolic compound.

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.

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.

Copigmentation is a phenomenon where pigmentation due to anthocyanidins is reinforced by the presence of other colorless flavonoids known as cofactors or “copigments”. This occurs by the formation of a non-covalently-linked complex.

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 class of chemical compounds

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.

Oxovitisin group of chemical compounds

Oxovitisins are a type of pyranoanthocyanin with a pyranone (2-pyrone) component found in aged Port wines. They do not contain an oxonium ion component, as anthocyanins do. Therefore, they do not have an absorption maximum at 520 nm. Oxovitisins are stable yellowish pigments with similar unique spectral features, displaying only a pronounced broad band around 370 nm in the UV−vis spectrum.

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.

Anthocyanone A chemical compound

Anthocyanone A is a degradation product of malvidin 3-O-glucoside under acidic conditions. It is found in wine.

References

  1. Oenin on answers.com
  2. Di Justo, Patrick (Aug 30, 2011). "What's Inside: Red Wine". Wired. Condé Nast.
  3. Houbiers, Chantal; Lima, João C.; Maçanita, António L.; Santos, Helena (1998). "Color Stabilization of Malvidin 3-Glucoside: Self-Aggregation of the Flavylium Cation and Copigmentation with the Z-Chalcone Form". The Journal of Physical Chemistry B. 102 (18): 3578. doi:10.1021/jp972320j.
  4. Malien-Aubert, C; Dangles, O; Amiot, MJ (2002). "Influence of procyanidins on the color stability of oenin solutions". Journal of Agricultural and Food Chemistry. 50 (11): 3299–305. doi:10.1021/jf011392b. PMID   12010001.
  5. Sarni-Manchado, Pascale; Cheynier, Véronique; Moutounet, Michel (1997). "Reactions of polyphenoloxidase generated caftaric acid o-quinone with malvidin 3-O-glucoside". Phytochemistry. 45 (7): 1365. doi:10.1016/S0031-9422(97)00190-8.