Oenin

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Oenin
Malvidin-3-glucoside.svg
Identifiers
CAS number 7228-78-6 YesY
PubChem 443652
ChemSpider 391785 N
ChEMBL CHEMBL403236 N, CHEMBL602754
Jmol-3D images Image 1
Properties
Molecular formula C23H25O12+, C23H25ClO12 (chloride)
Molar mass 493.43 g/mol, 528.89 g/mol (chloride)
Appearance dark brown powder (chloride)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
UV visible spectrum of malvidin 3-O-glucoside.

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]

References[edit]

  1. ^ Oenin on answers.com
  2. ^ Di Justo, Patrick (Aug 30, 2011). "What’s Inside: Red Wine". Wired (Condé Nast). 
  3. ^ 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 theZ-Chalcone Form". The Journal of Physical Chemistry B 102 (18): 3578. doi:10.1021/jp972320j. 
  4. ^ 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. 
  5. ^ 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.