Vitisin A (pyranoanthocyanin)

For other uses, see Vitisin A.

Vitisin A
Names

IUPAC name 5′′-Formyl-3-(β-D-glucopyranosyloxy)-4′,7-dihydroxy-3′,5′-dimethoxy-6′′-oxo-1,6′′-dihydropyranoflavylium
Systematic IUPAC name 3-Formyl-8-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-2-oxo-4-{oxy}-2H-pyranobenzopyran-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/s1Key: DYYPRYJWENTOEN-DMRYIZGCSA-O
SMILES O=CC1=C2C3=C(OC1=O)C=C(O)C=C3()C(C4=CC(OC)=C(O)C(OC)=C4)=C2O5O(CO)(O)(O)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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Vitisin A is a natural phenol found in red wines. It is a pyranoanthocyanin.

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

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

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