Oenin
From Wikipedia the free encyclopedia
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| Names | |
|---|---|
| IUPAC name 3-(β-D-Glucopyranosyloxy)-4′,5,7-trihydroxy-3′,5′-dimethoxyflavylium | |
| Systematic IUPAC name 5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4-benzopyran-1-ylium | |
| Other names Enin Malvidin-3-glucoside Malvidin 3-O-glucoside | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.027.847 |
| KEGG | |
PubChem CID | |
| UNII | |
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). | |
Oenin is an anthocyanin. It is the 3-glucoside of malvidin. It is one of the red pigments found in the skin of purple grapes[1] and in wine.[2]
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] In the presence of procyanidin C2, the red color of oenin appears more stable. However, the HPLC chromatogram shows a decrease in the amplitude of the peaks of oenin and procyanidin C2. Concomitantly, a new peak appears with a maximal absorption in the red region. This newly formed pigment probably comes from the condensation of oenin and procyanidin C2.[4]
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.[5]
See also[edit]
- Phenolic compounds in wine
- Wine color
- Malvidin glucoside-ethyl-catechin
- Anthocyanone A, a degradation product of oenin found in wine
References[edit]
- ^ Oenin on answers.com
- ^ Di Justo, Patrick (Aug 30, 2011). "What's Inside: Red Wine". Wired. Condé Nast.
- ^ Houbiers, Chantal; Lima, João C.; Maçanita, António L.; Santos, Helena (1998). "Color Stabilization of Malvidin 3-Glucoside: Self-Aggregation of the Flavylium Cation and Copigmentation with the Z-Chalcone Form". The Journal of Physical Chemistry B. 102 (18): 3578. doi:10.1021/jp972320j.
- ^ Malien-Aubert, C; Dangles, O; Amiot, MJ (2002). "Influence of procyanidins on the color stability of oenin solutions". Journal of Agricultural and Food Chemistry. 50 (11): 3299–305. doi:10.1021/jf011392b. PMID 12010001.
- ^ Sarni-Manchado, Pascale; Cheynier, Véronique; Moutounet, Michel (1997). "Reactions of polyphenoloxidase generated caftaric acid o-quinone with malvidin 3-O-glucoside". Phytochemistry. 45 (7): 1365. doi:10.1016/S0031-9422(97)00190-8.