Malvidin glucoside-ethyl-catechin
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Names | |
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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) |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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]
References
- ^ Malvidin glucoside-ethyl-catechin on Yeast Metabolome Database
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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
- v
- t
- e
- 5-Desoxy-peonidin
- Aurantinidin
- Cyanidin
- 6-Hydroxycyanidin
- Delphinidin
- Fisetinidin
- Guibourtinidin
- Pelargonidin
- Robinetinidin
- 5-Desoxy-malvidin
- Capensinidin
- Europinidin
- Hirsutidin
- Kaempferidinidin
- Malvidin
- Peonidin
- Petunidin
- Pulchellidin
- Rosinidin
(anthocyaninidin glycosides)
- Callistephin (Pelargonidin 3-O-glucoside)
- Chrysanthemin (Cyanidin 3-O-glucoside)
- Myrtillin (Delphinidin 3-O-glucoside)
- Oenin (Malvidin 3-O-glucoside)
- Peonidin 3-O-glucoside
- Petunidin 3-O-glucoside
- Pulchellidin 3-glucoside
Diglucosides:
- Cyanin (Cyanidin 3,5-O-diglucoside)
- Delphin (Delphinidin 3,5-O-diglucoside)
- Malvin (Malvidin 3,5-diglucoside)
- Pelargonin (Pelargonidin 3,5-O-diglucoside)
- Peonin (Peonidin 3,5-O-diglucoside)
- Petunin (Petunidin 3,5-O-diglucoside)
Others glycosides:
- Antirrhinin (Cyanidin 3-O-rutinoside)
- Ideain (Cyanidin 3-O-galactoside)
- Delphinidin 3-O-rhamnoside
- Petunidin 3-O-arabinoside
- Petunidin 3-O-galactoside
- Petunidin 3-O-rhamnoside
- Petunidin 3-O-rutinoside
- Primulin (Malvidin 3-O-galactoside)
- Pulchellidin 3-rhamnoside
- Tulipanin (Delphinidin 3-O-rutinoside)
Acetylated anthocyanins | |
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Coumaroylated anthocyanins (cis- and trans-) |
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Caffeoylated anthocyanins |
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Malonylated anthocyanins |
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Acylated anthocyanin diglycosides |
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- Malvidin glucoside-ethyl-catechin
- Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Metalloanthocyanins (commelinin)
- Cyanosalvianin
- Protocyanin
- Protodelphin)
- Pyranoanthocyanins
- Copigmentation
- Anthocyanone A (degradation product of oenin)
- Malvone (oxidation product of malvin)