Oenin

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Oenin
Malvidin-3-glucoside.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C23H24O12/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27)/p+1/t17-,19-,20+,21-,23-/m1/s1 X mark.svgN
    Key: PXUQTDZNOHRWLI-OXUVVOBNSA-O X mark.svgN
  • InChI=1/C23H24O12/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27)/p+1/t17-,19-,20+,21-,23-/m1/s1
    Key: PXUQTDZNOHRWLI-JIKKCJRGBW
  • COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O
Properties
C23H25O12+, C23H25ClO12 (chloride)
Molar mass 493.43 g/mol, 528.89 g/mol (chloride)
Appearancedark 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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UV visible spectrum of malvidin 3-O-glucoside. MalvidinG UV visible spectrum.PNG
UV visible spectrum of malvidin 3-O-glucoside.

Oenin is an anthocyanin. It is the 3-O-glucoside of malvidin (malvidin-3-O-glucoside). It is one of the red pigments found in purple grape skins and red wine. [1] [2]

Color stabilization of oenin 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]

Oenin 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

References

  1. ↑ Zhang B, Wang Q, Zhou PP, Li NN, Han SY (May 2020). "Copigmentation evidence of oenin with phenolic compounds: A comparative study of spectrographic, thermodynamic and theoretical data" . Food Chemistry. 313 126163. doi:10.1016/j.foodchem.2020.126163. PMID   31945702.
  2. ↑ He F, Liang NN, Mu L, Pan QH, Wang J, Reeves MJ, Duan CQ (February 2012). "Anthocyanins and their variation in red wines I. Monomeric anthocyanins and their color expression". Molecules. 17 (2): 1571–601. doi: 10.3390/molecules17021571 . PMC   6268338 . PMID   22314380.
  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 the Z-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. Bibcode:2002JAFC...50.3299M. 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. Bibcode:1997PChem..45.1365S. doi:10.1016/S0031-9422(97)00190-8.
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