Vitisin B (pyranoanthocyanin)

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
CAS Number	184362-10-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:147426;
ChemSpider	58191428 ;
PubChem CID	44195285;
UNII	C3JJ5TC7LJ ;
CompTox Dashboard (EPA)	DTXSID301311376 ;
	InChI 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 Key: ZFFLAEFKTXRRFR-FHBCLOHASA-O ; 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;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox references

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

References

^ 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 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
^ 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
^ 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

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[Nixdorf-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

[1]

[2]

[3]

[4]

[5]

v t e Pyranoanthocyanidins
Vitisins	Vitisin A Vitisin B
Pinotins	Pinotin A
Portosins	Vinylpyranomalvidin-3O-glucoside-procyanidin dimer VinylpyranoMv-3-coumaroylglucoside-procyanidin dimer Vinylpyranomalvidin-3O-glucoside-catechin Vinylpyranomalvidin-3O-coumaroylglucoside-catechin Vinylpyranomalvidin-3O-phenol Vinylpyranopetunidin-3O-glucoside-catechin Vinylpyranopeonidin-3O-glucoside-catechin Vinylpyranomalvidin-3O-acetylglucoside-catechin

See also

References