Oenin is an anthocyanin. It is the 3-glucoside of malvidin. It can be found in the skin of purple grapes[1] and in wine. It is the red pigment in red wine.[2]
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| Names | |
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| IUPAC name
(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
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| Other names
Enin
Malvidin-3-glucoside Malvidin 3-O-glucoside | |
| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ECHA InfoCard | 100.027.847 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C23H25O12+, C23H25ClO12 (chloride) | |
| Molar mass | 493.43 g/mol, 528.89 g/mol (chloride) |
| Appearance | dark brown powder (chloride) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Color stabilization of malvidin 3-glucoside at a higher pH can be explained by self-aggregation of the flavylium cation and copigmentation with the Z-chalcone form.[3]
Malvidin 3-glucoside alone is not oxidized in the presence of grape polyphenol oxidase, whereas it is degraded in the presence of a crude grape PPO extract and of caftaric acid forming anthocyanidin-caftaric acid adducts.[4]
See also
References
- ^ Oenin on answers.com
- ^ http://www.wired.com/magazine/2011/08/st_whatsinside_redwine/
- ^ Color Stabilization of Malvidin 3-Glucoside: Self-Aggregation of the Flavylium Cation and Copigmentation with the Z-Chalcone Form. Chantal Houbiers, João C. Lima, António L. Maçanita and Helena Santos, J. Phys. Chem. B, 1998, 102 (18), pages 3578–3585, doi:10.1021/jp972320j
- ^ Reactions of polyphenoloxidase generated caftaricacido-quinone with malvidin 3-O-glucoside. Pascale Sarni-Manchado, Véronique Cheynier and Michel Moutounet, Phytochemistry, August 1997, Volume 45, Issue 7, pages 1365–1369, doi:10.1016/S0031-9422(97)00190-8