Oxovitisin A

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)	Interactive image;
PubChem CID	136740013;
	InChI 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;
	SMILES 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
Chemical formula	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

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]

References

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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[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