Vitisin A (pyranoanthocyanin)

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	184362-09-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	8500967 ;
PubChem CID	10325504;
CompTox Dashboard (EPA)	DTXSID20438083 ;
	InChI 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;
	SMILES 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). verify (what is ?) Infobox references

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

This article about an aromatic compound is a stub. You can help Wikipedia by expanding it.