Vitisin B (pyranoanthocyanin)

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

For other uses, see Vitisin B.
Vitisin B
Chemical structure of vitisin B
Names
IUPAC name
3-(β-D-Glucopyranosyloxy)-4′,7-dihydroxy-3′,5′-dimethoxypyrano[4′′,3′′,2′′:4,5]flavylium
Systematic IUPAC name
8-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4-pyrano[4,3,2-de][1]benzopyran-1-ylium
Other names
Pyranomalvidin-3-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C25H24O12/c1-32-15-5-10(6-16(33-2)19(15)28)23-24(37-25-22(31)21(30)20(29)17(9-26)36-25)12-3-4-34-13-7-11(27)8-14(35-23)18(12)13/h3-8,17,20-22,25-26,29-31H,9H2,1-2H3,(H-,27,28)/p+1/t17-,20-,21+,22-,25+/m1/s1 ☒N
    Key: ZFFLAEFKTXRRFR-FHBCLOHASA-O ☒N
  • InChI=1/C25H24O12/c1-32-15-5-10(6-16(33-2)19(15)28)23-24(37-25-22(31)21(30)20(29)17(9-26)36-25)12-3-4-34-13-7-11(27)8-14(35-23)18(12)13/h3-8,17,20-22,25-26,29-31H,9H2,1-2H3,(H-,27,28)/p+1/t17-,20-,21+,22-,25+/m1/s1
    Key: ZFFLAEFKTXRRFR-IPEXBSMVBT
  • COc1cc(cc(c1O)OC)c2c(c3c4c([o+]2)cc(cc4OC=C3)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
Properties
C25H25O12+
Molar mass 517.45 g/mol
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

See also

References
  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
  2. Formation of the highly stable pyranoanthocyanins (vitisins A and B) in red wines by the addition of pyruvic acid and acetaldehyde. A. Morata, F. Calderón, M.C. González, M.C. Gómez-Cordovés and J.A. Suárez, Food Chemistry, Volume 100, Issue 3, 2007, Pages 1144-1152, doi:10.1016/j.foodchem.2005.11.024
  3. A novel synthetic pathway to vitisin B compounds. Joana Oliveira, Victor de Freitas and Nuno Mateus, Tetrahedron Letters, Volume 50, Issue 27, 8 July 2009, Pages 3933-3935, doi:10.1016/j.tetlet.2009.04.072
  4. 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
  5. 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


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