Oenin

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Oenin

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
Other names Enin Malvidin-3-glucoside Malvidin 3-O-glucoside
Identifiers
CAS number	7228-78-6^Y
PubChem	443652
ChemSpider	391785^N
ChEMBL	CHEMBL403236^N, CHEMBL602754
Jmol-3D images	{{#if:COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O\|Image 1
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
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^N Key: PXUQTDZNOHRWLI-OXUVVOBNSA-O^N 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
Properties
Molecular formula	C₂₃H₂₅O₁₂⁺, C₂₃H₂₅ClO₁₂ (chloride)
Molar mass	493.43 g/mol, 528.89 g/mol (chloride)
Appearance	dark brown powder (chloride)
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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]

References

↑ 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 theZ-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.

v t e Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins	5-Desoxy-peonidin Aurantinidin Cyanidin 6-Hydroxycyanidin Delphinidin Fisetinidin Guibourtinidin Pelargonidin Robinetinidin

3-deoxyanthocyanidins	Apigeninidin Columnidin Diosmetinidin Gesneridin Luteolinidin Tricetinidin

O-methylated anthocyanidins	5-Desoxy-malvidin Capensinidin Europinidin Hirsutidin Malvidin Peonidin Petunidin Pulchellidin Rosinidin

Anthocyanins	Antirrhinin (Cyanidin-3-O-rutinoside) Callistephin (Pelargonidin 3-O-glucoside) Chrysanthemin (Cyanidin-3-O-glucoside) Malvin (Malvidin 3,5-diglucoside) Myrtillin (Delphinidin-3-O-glucoside) Oenin (Malvidin-3-O-glucoside) Peonidin-3-O-glucoside Petunidin 3,5-O-diglucoside Petunidin 3-O-arabinoside Petunidin 3-O-galactoside Petunidin-3-O-glucoside Petunidin 3-O-rhamnoside Petunidin-3-O-rutinoside Primulin (Malvidin-3-O-galactoside) Pulchellidin 3-glucoside Pulchellidin 3-rhamnoside Tulipanin (Delphinidin 3-O-rutinoside)

Acetylated anthocyanins	Cyanidin-3-O-(6-acetyl)-glucoside Delphinidin-3-O-(6-acetyl)-glucoside Malvidin-3-O-(6-acetyl)-glucoside Petunidin-3-O-(6-acetyl)-galactoside Petunidin-3-O-(6-acetyl)-glucoside Peonidin-3-O-(6-acetyl)-glucoside

Coumaroylated anthocyanins (cis- and trans-)	Cyanidin-3-O-(6-p-coumaroyl)glucoside Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) Petunidin-3-O-(6-p-coumaroyl)glucoside Peonidin-3-O-(6-p-coumaroyl)glucoside

Caffeoylated anthocyanins	Malvidin-3-O-(6-p-caffeoyl)glucoside Peonidin-3-O-(6-p-caffeoyl)glucoside Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside))

p-hydroxybenzoylated anthocyanins	Violdelphin

Flavanol-anthocyanin adducts	Malvidin glucoside-ethyl-catechin

Misc.	Metalloanthocyanins (Commelinin Cyanosalvianin Protocyanin Protodelphin) Pyranoanthocyanins Copigmentation

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Oenin

See also

References