Oenin

Oenin
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
CAS Number	7228-78-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL403236 ; ChEMBL602754 ;
ChemSpider	391785 ;
ECHA InfoCard	100.027.847
KEGG	C12140 ;
PubChem CID	443652;
UNII	B34F52D7NB ;
CompTox Dashboard (EPA)	DTXSID30332124 ;
	InChI 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 Key: PXUQTDZNOHRWLI-OXUVVOBNSA-O ; 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;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox references

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]

References

^ 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.
^ 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. PMID 22314380.
^ 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.

[zhang-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.

[he-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. 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. 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.

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[2]

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See also

References