Vitisin B (pyranoanthocyanin)

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

Quick Facts Names, Identifiers ...

Vitisin B
Names
Chemical structure of vitisin B
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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:147426
ChemSpider	58191428^N
PubChem CID	44195285
UNII	C3JJ5TC7LJ^Y
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^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
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). N verify (what is ^YN ?) Infobox references

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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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
CAS Number	184362-10-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:147426
ChemSpider	58191428^N
PubChem CID	44195285
UNII	C3JJ5TC7LJ^Y
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^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
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). N verify (what is ^YN ?) Infobox references

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^Y

3D model (JSmol)

Interactive image

ChEBI

CHEBI:147426

ChemSpider

58191428^N

PubChem CID

44195285

UNII

C3JJ5TC7LJ^Y

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^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