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Revision as of 14:42, 18 July 2011 editNono64 (talk | contribs)Autopatrolled, Pending changes reviewers, Rollbackers96,246 editsm Category:Phenolic compounds in wine← Previous edit Latest revision as of 15:07, 24 December 2024 edit undoCitation bot (talk | contribs)Bots5,452,046 edits Alter: title, template type. Added magazine. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:O-methylated anthocyanins | #UCB_Category 4/5 
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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 400999419 | verifiedrevid = 440126520
| name = Oenin | Name = Oenin
| ImageFile = Malvidin-3-glucoside.svg | ImageFile = Malvidin-3-glucoside.svg
| ImageSize = 300px | ImageSize = 300px
| IUPACName = 3-(β-<small>D</small>-Glucopyranosyloxy)-4′,5,7-trihydroxy-3′,5′-dimethoxyflavylium
| IUPACName = (2''S'',3''R'',4''S'',5''S'',6''R'')-2-oxy-6-(hydroxymethyl)oxane-3,4,5-triol
| SystematicName = 5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{oxy}-1λ<sup>4</sup>-benzopyran-1-ylium
| OtherNames = Enin<br>Malvidin-3-glucoside<br>Malvidin 3-O-glucoside | OtherNames = Enin<br>Malvidin-3-glucoside<br>Malvidin 3-O-glucoside
| Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo = 7228-78-6
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | PubChem = 443652
⚫ | CASNo = 7228-78-6
⚫ | SMILES = COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=2)O)O)OC4C(C(C(C(O4)CO)O)O)O
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B34F52D7NB
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C12140
⚫ | PubChem = 443652
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 403236
| ChEMBL2_Ref = {{ebicite|changed|EBI}}
| ChEMBL2 = 602754
⚫ | SMILES = COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=2)O)O)OC4C(C(C(C(O4)CO)O)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 391785
| 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
| InChIKey = PXUQTDZNOHRWLI-JIKKCJRGBW
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PXUQTDZNOHRWLI-OXUVVOBNSA-O
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>23</sub>H<sub>25</sub>O<sub>12</sub><sup>+</sup> | Formula = C<sub>23</sub>H<sub>25</sub>O<sub>12</sub><sup>+</sup>, C<sub>23</sub>H<sub>25</sub>ClO<sub>12</sub> (chloride)
| MolarMass = 493.43 g/mol | MolarMass = 493.43 g/mol, 528.89 g/mol (chloride)
| Appearance = dark brown powder (chloride)
| ExactMass = 493.134601 u
| Appearance = | Density =
| Density = | MeltingPt =
| MeltingPt = | BoilingPt =
| BoilingPt = | Solubility =
| Solubility =
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
]
'''Oenin''' is an ]. It is the 3-] of ]. It can be found in the skin of purple ]s<ref></ref> and in wine. '''Oenin''' is an ]. It is the 3-] of ]. It is one of the red pigments found in the skin of purple ]s<ref></ref> and in wine.<ref>{{cite magazine |last= Di Justo |first= Patrick |title= What's Inside: Red Wine |magazine= Wired |publisher= Condé Nast |date= Aug 30, 2011 |url=https://www.wired.com/magazine/2011/08/st_whatsinside_redwine/ }}</ref>


Color stabilization of malvidin 3-glucoside at a higher pH can be explained by self-aggregation of the ] cation and copigmentation with the Z-chalcone form.<ref>{{Cite journal|doi=10.1021/jp972320j|title=Color Stabilization of Malvidin 3-Glucoside: Self-Aggregation of the Flavylium Cation and Copigmentation with the Z-Chalcone Form|year=1998|last1=Houbiers|first1=Chantal|last2=Lima|first2=João C.|last3=Maçanita|first3=António L.|last4=Santos|first4=Helena|journal=The Journal of Physical Chemistry B|volume=102|issue=18|pages=3578}}</ref> In the presence of ], 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.<ref>{{Cite journal|pmid=12010001|year=2002|last1=Malien-Aubert|first1=C|last2=Dangles|first2=O|last3=Amiot|first3=MJ|title=Influence of procyanidins on the color stability of oenin solutions|volume=50|issue=11|pages=3299–305|journal=Journal of Agricultural and Food Chemistry|doi=10.1021/jf011392b}}</ref>
⚫ ==See also==

Malvidin 3-glucoside alone is not oxidized in the presence of grape ], whereas it is degraded in the presence of a crude grape PPO extract and of ] forming ]s.<ref>{{Cite journal|doi=10.1016/S0031-9422(97)00190-8|title=Reactions of polyphenoloxidase generated caftaric acid o-quinone with malvidin 3-O-glucoside|year=1997|last1=Sarni-Manchado|first1=Pascale|last2=Cheynier|first2=Véronique|last3=Moutounet|first3=Michel|journal=Phytochemistry|volume=45|issue=7|pages=1365}}</ref>

⚫ == See also ==
* ] * ]
* ]
* ]
* ], a degradation product of oenin found in wine


==References== == References ==
{{Reflist}} {{Reflist}}


{{Anthocyanins}} {{Anthocyanins}}


] ]
]

{{Natural-phenol-stub}}

]
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