Oxovitisin A

Oxovitisin A is an oxovitisin, a type of pyranoanthocyanin with a pyranone (2-pyrone) component. It is found in aged Port wines. It does not contain an oxonium ion component (flavylium cation), as anthocyanins do. Therefore, it does not have an absorption maximum at 520 nm. Oxovitisins are stable yellowish pigments with similar unique spectral features, displaying only a pronounced broad band around 370 nm in the UV−vis spectrum. It is an oxidative derivative of carboxypyranomalvidin-3-glucoside (vitisin A).[1]

Oxovitisin A
Chemical structure of oxovitisin A
Names
IUPAC name
7-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,8-dioxatricyclo[7.3.1.05,13]trideca-1(12),3,5(13),6,9-pentaen-11-one
Other names
Pyranone-malvidin-3-glucoside
Identifiers
3D model (JSmol)
  • InChI=1S/C25H24O13/c1-33-14-3-9(4-15(34-2)19(14)29)23-24(38-25-22(32)21(31)20(30)16(8-26)37-25)11-7-17(28)35-12-5-10(27)6-13(36-23)18(11)12/h3-7,16,20-22,25-26,28-32H,8H2,1-2H3/t16-,20-,21+,22-,25+/m1/s1
    Key: ZHRWIFDUQBVARB-DCNRUEEBSA-N
  • COC1=CC(=CC(=C1O)OC)C2=C(C3=C4C(=CC(=O)C=C4O2)OC(=C3)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
Properties
C25H24O13
Molar mass 532.45 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Oxovitisins: A New Class of Neutral Pyranone-anthocyanin Derivatives in Red Wines. Jingren He, Joana Oliveira, Artur M. S. Silva, Nuno Mateus and Victor De Freitas, J. Agric. Food Chem., 2010, 58 (15), pages 8814–8819, doi:10.1021/jf101408q


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