Malvidin glucoside-ethyl-catechin

Last updated
Malvidin glucoside-ethyl-catechin
Malvidin glucoside-ethyl-catechin.svg
Names
Preferred IUPAC name
8-{(1Ξ)-1-[(2R*,3S*)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]ethyl}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4-benzopyran-1-ylium
Other names
8,8-linked malvidin-3-glucose-ethyl-(epi)catechin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C40H40O18/c1-14(30-23(46)11-20(43)17-9-25(48)36(57-38(17)30)15-4-5-19(42)22(45)6-15)31-24(47)12-21(44)18-10-28(55-40-35(52)34(51)33(50)29(13-41)56-40)37(58-39(18)31)16-7-26(53-2)32(49)27(8-16)54-3/h4-8,10-12,14,25,29,33-36,40-41,48,50-52H,9,13H2,1-3H3,(H6-,42,43,44,45,46,47,49)/p+1/t14?,25?,29-,33-,34+,35-,36?,40-/m1/s1
    Key: OWEZHPRMUFSMFC-OGEOSVLCSA-O
  • CC(c1c2[o+]c(c(cc2c(O)cc1O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)-c1cc(OC)c(O)c(c1)OC)c1c2OC(C(O)Cc2c(O)cc1O)c1cc(O)c(O)cc1
Properties
C40H40O18
Molar mass 809.75 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Malvidin glucoside-ethyl-catechin is a flavanol-anthocyanin adduct. [1] [2] 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. [3] [4]

This compound has a better color stability at pH 5.5 than malvidin-3O-glucoside. When the pH was increased from 2.2 to 5.5, the solution of the pigment became progressively more violet (λmax = 560 nm at pH 5.5), whereas similar solutions of the anthocyanin were almost colorless at pH 4.0. [5]

Other types of aldehyde, such as isovaleraldehyde, benzaldehyde, propionaldehyde, isobutyraldehyde, formaldehyde or 2-methylbutyraldehyde, show the same reactivity in model solutions. [6]

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 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.

Catechin A type of natural phenol and antioxidant. A plant secondary metabolite

Catechin is a flavan-3-ol, a type of natural phenol and antioxidant. It is a plant secondary metabolite. It belongs to the group of flavan-3-ols, part of the chemical family of flavonoids.

Delphinidin Chemical compound

Delphinidin is an anthocyanidin, a primary plant pigment, and also an antioxidant. Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape that produces Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates, and bilberries.

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.

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.

Anthocyanin

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.

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.

Myrtillin Chemical compound

Myrtillin is an anthocyanin. It is the 3-glucoside of delphinidin. It can be found in all green plants, most abundantly in blackcurrant, blueberry, huckleberry, bilberry leaves and in various myrtles, roselle plants, and Centella asiatica plant. It is also present in yeast and oatmeal. The sumac fruit's pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.

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.

Naturally occurring phenols

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.

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.

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.

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.

Oxovitisin

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

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.

References

  1. Malvidin glucoside-ethyl-catechin on Yeast Metabolome Database
  2. Atanasova, Vessela; Fulcrand, Hélène; Cheynier, Véronique; Moutounet, Michel (2002). "Effect of oxygenation on polyphenol changes occurring in the course of wine-making". Analytica Chimica Acta. 458: 15–27. doi:10.1016/S0003-2670(01)01617-8.
  3. Morata, A; González, C; Suárez-Lepe, JA (2007). "Formation of vinylphenolic pyranoanthocyanins by selected yeasts fermenting red grape musts supplemented with hydroxycinnamic acids". International Journal of Food Microbiology. 116 (1): 144–52. doi:10.1016/j.ijfoodmicro.2006.12.032. PMID   17303275.
  4. Asenstorfer, Robert E.; Lee, David F.; Jones, Graham P. (2006). "Influence of structure on the ionisation constants of anthocyanin and anthocyanin-like wine pigments". Analytica Chimica Acta. 563 (1–2): 10–14. doi:10.1016/j.aca.2005.09.040.
  5. Escribano-Bailón, Teresa; Álvarez-García, Marta; Rivas-Gonzalo, Julian C.; Heredia, Francisco J.; Santos-Buelga, Celestino (2001). "Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin". Journal of Agricultural and Food Chemistry. 49 (3): 1213–7. doi:10.1021/jf001081l. PMID   11312838.
  6. Pissarra, J.; Mateus, N.; Rivas-Gonzalo, J.; Santos Buelga, C.; Freitas, V. (2003). "Reaction Between Malvidin 3-Glucoside and (+)-Catechin in Model Solutions Containing Different Aldehydes". Journal of Food Science. 68 (2): 476–481. doi:10.1111/j.1365-2621.2003.tb05697.x. INIST:15183380.

See also