Malvidin glucoside-ethyl-catechin

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Malvidin glucoside-ethyl-catechin
Chemical structure of malvidin glucoside-ethyl-catechin
Identifiers
Jmol-3D images Image 1
Properties
Molecular formula C41H43O17
Molar mass 807.76 g/mol
Except where noted otherwise, 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[edit]

  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. 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: 10. 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. doi:10.1111/j.1365-2621.2003.tb05697.x. INIST:15183380. 

See also[edit]