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Contents

   



(Top)
  


1 See also  




2 References  




3 External links  













Vitisin A (pyranoanthocyanin)






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From Wikipedia, the free encyclopedia
  

For other uses, see Vitisin A.
Vitisin A
Chemical structure of vitisin A
Names
IUPAC name

5′′-Formyl-3-(β-D-glucopyranosyloxy)-4′,7-dihydroxy-3′,5′-dimethoxy-6′′-oxo-1,6′′-dihydropyrano[4′′,3′′,2′′:4,5]flavylium

Systematic IUPAC name

3-Formyl-8-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-2-oxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-pyrano[4,3,2-de][1]benzopyran-6-ium

Other names

Malvidin 3-O-glucoside pyruvic acid
Malvidin 3-O-glucoside pyruvic adduct
5-carboxypyranomalvidin-3-glucoside

Identifiers

CAS Number

3D model (JSmol)
ChemSpider

PubChem CID

CompTox Dashboard (EPA)

  • InChI=1S/C26H24O14/c1-35-14-3-9(4-15(36-2)19(14)30)23-24(40-26-22(33)21(32)20(31)16(8-28)39-26)17-11(7-27)25(34)38-13-6-10(29)5-12(37-23)18(13)17/h3-7,16,20-22,26,28-33H,8H2,1-2H3/p+1/t16-,20-,21+,22-,26+/m1/s1

    Key: DYYPRYJWENTOEN-DMRYIZGCSA-O

  • O=CC1=C2C3=C(OC1=O)C=C(O)C=C3[O+]([H])C(C4=CC(OC)=C(O)C(OC)=C4)=C2O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O

Properties

Chemical formula

 C26H25O14+
Molar mass 561.46 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

☒N verify (what is checkY☒N ?)

Infobox references

Vitisin A is a natural phenol found in red wines.[1][2][3] It is a pyranoanthocyanin.[4][5]

See also[edit]

References[edit]

  1. ^ Brazilian red wines made from the hybrid grape cultivar Isabel: Phenolic composition and antioxidant capacity. Suzana Lucy Nixdorf and Isidro Hermosín-Gutiérrez, Analytica Chimica Acta, Volume 659, Issues 1-2, 5 February 2010, Pages 208-215, doi:10.1016/j.aca.2009.11.058
  • ^ Formation of vitisin A during red wine fermentation and maturation. Robert E. Asenstrfer, Andrew J. Markides, Patrick G. Iland and Graham P. Jones, Australian Journal of Grape and Wine Research, Volume 9, Issue 1, pages 40–46, April 2003, doi:10.1111/j.1755-0238.2003.tb00230.x
  • ^ Vitisin A content in chilean wines from Vitis vinifera cv. cabernet sauvignon and contribution to the color of aged red wines. Schwarz Michael, Quast Peter, Von Baer Dietrich and Winterhalter Peter, Journal of agricultural and food chemistry, 2003, vol. 51, no21, pp. 6261-626, INIST 15183115
  • ^ Charge equilibria and pK values of 5-carboxypyranomalvidin-3-glucoside (vitisin A) by electrophoresis and absorption spectroscopy. Robert E. Asenstorfer and Graham P. Jones, Tetrahedron, Volume 63, Issue 22, 28 May 2007, Pages 4788-4792, doi:10.1016/j.tet.2007.03.052
  • ^ Effect of acetaldehyde and several acids on the formation of vitisin A in model wine anthocyanin and colour evolution. Romero C. and Bakker J., International journal of food science & technology, 2000, vol. 35, no. 1, pp. 129-140, INIST 1283952

    • External links[edit]


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