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

doi:10.1016/j.aca.2009.11.058

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

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

Vitisin A on www.phenol-explorer.eu

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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[Nixdorf-1] doi:10.1016/j.aca.2009.11.058

[2] doi:10.1111/j.1755-0238.2003.tb00230.x

[3] 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

[4] 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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[2]

[3]

[4]

[5]

See also

References

External links