290:
195:
459:
35:
426:
496:, 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.
1368:
586:
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".
125:
313:
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
323:
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
439:
649:
Sarni-Manchado, Pascale; Cheynier, Véronique; Moutounet, Michel (1997). "Reactions of polyphenoloxidase generated caftaric acid o-quinone with malvidin 3-O-glucoside".
339:
1234:
694:
1247:
1477:
1459:
1468:
1378:
1351:
1561:
1450:
1445:
530:
304:
1260:
1273:
1221:
1310:
1297:
1174:
1156:
1183:
687:
508:
247:
1192:
1165:
1147:
614:
Malien-Aubert, C; Dangles, O; Amiot, MJ (2002). "Influence of procyanidins on the color stability of oenin solutions".
1437:
268:
976:
962:
520:
446:
1020:
1057:
1006:
1112:
1075:
1066:
1093:
1084:
949:
940:
680:
190:
1102:
931:
152:
145:
1016:
972:
61:
47:
823:
721:
488:
Color stabilization of malvidin 3-glucoside at a higher pH can be explained by self-aggregation of the
1369:
delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside)
843:
771:
1507:
285:
1364:
1334:
91:
1517:
672:
1497:
568:
500:
1501:
458:
1523:
736:
631:
1539:
1388:
1002:
658:
623:
596:
362:
172:
256:
101:
289:
194:
1533:
1528:
751:
535:
493:
417:
662:
1555:
901:
789:
761:
703:
504:
183:
34:
891:
863:
828:
804:
799:
794:
779:
756:
726:
236:
1512:
1402:
1139:
1037:
878:
833:
746:
741:
470:
992:
838:
784:
525:
397:
163:
503:, whereas it is degraded in the presence of a crude grape PPO extract and of
66:
5,7-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{oxy}-1λ-benzopyran-1-ylium
1117:
911:
868:
858:
707:
489:
474:
635:
853:
848:
731:
478:
1374:
492:
cation and copigmentation with the Z-chalcone form. In the presence of
223:
627:
600:
1047:
986:
555:
136:
499:
Malvidin 3-glucoside alone is not oxidized in the presence of grape
416:
Except where otherwise noted, data are given for materials in their
347:
COC1=CC(=CC(=C1O)OC)C2=C(C=C3C(=CC(=CC3=2)O)O)OC4C(C(C(C(O4)CO)O)O)O
17:
211:
482:
457:
124:
114:
202:
676:
55:-Glucopyranosyloxy)-4′,5,7-trihydroxy-3′,5′-dimethoxyflavylium
481:. It is one of the red pigments found in the skin of purple
273:
434:
1490:
1436:
1344:
1327:
1290:
1204:
1138:
1131:
877:
813:
770:
714:
402:493.43 g/mol, 528.89 g/mol (chloride)
235:
100:
1337:(malvidin 3-(6″-malonylglucoside)-5-glucoside)
538:, a degradation product of oenin found in wine
462:UV visible spectrum of malvidin 3-O-glucoside.
688:
8:
1135:
695:
681:
673:
616:Journal of Agricultural and Food Chemistry
288:
193:
171:
26:
255:
548:
344:
309:
284:
184:
316:Key: PXUQTDZNOHRWLI-OXUVVOBNSA-O
151:
144:
7:
589:The Journal of Physical Chemistry B
509:anthocyanidin-caftaric acid adducts
326:Key: PXUQTDZNOHRWLI-JIKKCJRGBW
226:
210:
1478:Epiafzelechin(4α→8)pelargonidin 3-
567:Di Justo, Patrick (Aug 30, 2011).
25:
1446:Malvidin glucoside-ethyl-catechin
1383:-coumaroylrutinoside)-5-glucoside
1345:Acylated anthocyanin diglycosides
531:Malvidin glucoside-ethyl-catechin
1460:Epicatechin(4α→8)pelargonidin 3-
424:
33:
1469:Afzelechin(4α→8)pelargonidin 3-
1360:-coumarylglucoside)-5-glucoside
420:(at 25 °C , 100 kPa).
1536:(degradation product of oenin)
1:
1542:(oxidation product of malvin)
1451:Catechin(4α→8)pelargonidin 3-
663:10.1016/S0031-9422(97)00190-8
410:dark brown powder (chloride)
1438:Flavanol-anthocyanin adducts
1405:(Delphinidin 3-rutinoside-7-
882:(anthocyaninidin glycosides)
1578:
1205:Coumaroylated anthocyanins
989:(Malvidin 3,5-diglucoside)
817:-Methylated anthocyanidins
521:Phenolic compounds in wine
1562:O-methylated anthocyanins
1291:Caffeoylated anthocyanins
1113:Pulchellidin 3-rhamnoside
569:"What's Inside: Red Wine"
414:
355:
335:
300:
84:
72:
60:
46:
41:
32:
1421:-glucosyl)oxybenzoyl)-β-
1328:Malonylated anthocyanins
950:Pulchellidin 3-glucoside
715:3-Hydroxyanthocyanidins
1417:-(4-hydroxybenzoyl)-β-
1179:-(6-acetyl)galactoside
706:and their anthocyanin
463:
79:Malvidin 3-O-glucoside
1132:Acylated anthocyanins
772:3-Deoxyanthocyanidins
461:
62:Systematic IUPAC name
1282:-coumaroyl)glucoside
1269:-coumaroyl)glucoside
1256:-coumaroyl)glucoside
1243:-coumaroyl)glucoside
1230:-coumaroyl)glucoside
1197:-(6-acetyl)glucoside
1188:-(6-acetyl)glucoside
1170:-(6-acetyl)glucoside
1161:-(6-acetyl)glucoside
1152:-(6-acetyl)glucoside
556:Oenin on answers.com
77:Malvidin-3-glucoside
1498:Metalloanthocyanins
1319:-caffeoyl)glucoside
1306:-caffeoyl)glucoside
29:
1524:Pyranoanthocyanins
1482:-β-glucopyranoside
1473:-β-glucopyranoside
1464:-β-glucopyranoside
1455:-β-glucopyranoside
1032:Others glycosides:
995:(Pelargonidin 3,5-
501:polyphenol oxidase
464:
447:Infobox references
27:
1549:
1548:
1432:
1431:
1424:
1420:
1399:-glucopyranoside)
1398:
824:5-Desoxy-malvidin
737:6-Hydroxycyanidin
722:5-Desoxy-peonidin
628:10.1021/jf011392b
601:10.1021/jp972320j
455:Chemical compound
453:
452:
392:(chloride)
269:CompTox Dashboard
126:Interactive image
54:
16:(Redirected from
1569:
1422:
1418:
1396:
1391:(petunidin 3--5-
1136:
977:Delphinidin 3,5-
894:(Pelargonidin 3-
844:Kaempferidinidin
697:
690:
683:
674:
667:
666:
646:
640:
639:
622:(11): 3299–305.
611:
605:
604:
583:
577:
576:
564:
558:
553:
437:
431:
428:
427:
363:Chemical formula
293:
292:
277:
275:
259:
239:
228:
214:
197:
186:
175:
155:
148:
128:
104:
52:
37:
30:
21:
1577:
1576:
1572:
1571:
1570:
1568:
1567:
1566:
1552:
1551:
1550:
1545:
1486:
1428:
1379:Delphinidin 3-(
1340:
1323:
1286:
1206:
1200:
1127:
1120:(Delphinidin 3-
914:(Delphinidin 3-
881:
873:
809:
766:
710:
701:
671:
670:
648:
647:
643:
613:
612:
608:
585:
584:
580:
566:
565:
561:
554:
550:
545:
517:
456:
449:
444:
443:
442: ?)
433:
429:
425:
421:
391:
387:
383:
379:
375:
371:
365:
351:
348:
343:
342:
331:
328:
327:
324:
318:
317:
314:
308:
307:
296:
278:
271:
262:
242:
229:
217:
178:
158:
131:
118:
107:
94:
80:
78:
76:
68:
67:
56:
23:
22:
15:
12:
11:
5:
1575:
1573:
1565:
1564:
1554:
1553:
1547:
1546:
1544:
1543:
1537:
1534:Anthocyanone A
1531:
1529:Copigmentation
1526:
1521:
1515:
1510:
1508:Cyanosalvianin
1505:
1494:
1492:
1488:
1487:
1485:
1484:
1475:
1466:
1457:
1448:
1442:
1440:
1434:
1433:
1430:
1429:
1427:
1426:
1400:
1386:
1372:
1362:
1348:
1346:
1342:
1341:
1339:
1338:
1331:
1329:
1325:
1324:
1322:
1321:
1308:
1294:
1292:
1288:
1287:
1285:
1284:
1271:
1258:
1245:
1235:Delphinidin 3-
1232:
1218:
1216:
1202:
1201:
1199:
1190:
1181:
1172:
1163:
1157:Delphinidin 3-
1154:
1145:
1143:
1133:
1129:
1128:
1126:
1125:
1115:
1110:
1100:
1091:
1082:
1073:
1064:
1058:Delphinidin 3-
1055:
1045:
1029:
1028:
1021:Petunidin 3,5-
1014:
1000:
990:
984:
970:
953:
952:
947:
938:
929:
919:
909:
899:
885:
883:
875:
874:
872:
871:
866:
861:
856:
851:
846:
841:
836:
831:
826:
820:
818:
811:
810:
808:
807:
802:
797:
792:
787:
782:
776:
774:
768:
767:
765:
764:
759:
754:
752:Guibourtinidin
749:
744:
739:
734:
729:
724:
718:
716:
712:
711:
704:Anthocyanidins
702:
700:
699:
692:
685:
677:
669:
668:
651:Phytochemistry
641:
606:
578:
559:
547:
546:
544:
541:
540:
539:
536:Anthocyanone A
533:
528:
523:
516:
513:
494:procyanidin C2
473:. It is the 3-
454:
451:
450:
445:
423:
422:
418:standard state
415:
412:
411:
408:
404:
403:
400:
394:
393:
389:
385:
381:
377:
373:
369:
366:
361:
358:
357:
353:
352:
350:
349:
346:
338:
337:
336:
333:
332:
330:
329:
325:
322:
321:
319:
315:
312:
311:
303:
302:
301:
298:
297:
295:
294:
286:DTXSID30332124
281:
279:
267:
264:
263:
261:
260:
252:
250:
244:
243:
241:
240:
232:
230:
222:
219:
218:
216:
215:
207:
205:
199:
198:
188:
180:
179:
177:
176:
168:
166:
160:
159:
157:
156:
149:
141:
139:
133:
132:
130:
129:
121:
119:
112:
109:
108:
106:
105:
97:
95:
90:
87:
86:
82:
81:
74:
70:
69:
65:
64:
58:
57:
50:
44:
43:
39:
38:
24:
14:
13:
10:
9:
6:
4:
3:
2:
1574:
1563:
1560:
1559:
1557:
1541:
1538:
1535:
1532:
1530:
1527:
1525:
1522:
1519:
1516:
1514:
1511:
1509:
1506:
1503:
1499:
1496:
1495:
1493:
1491:Miscellaneous
1489:
1483:
1481:
1476:
1474:
1472:
1467:
1465:
1463:
1458:
1456:
1454:
1449:
1447:
1444:
1443:
1441:
1439:
1435:
1416:
1412:
1408:
1404:
1401:
1394:
1390:
1387:
1384:
1382:
1376:
1373:
1370:
1366:
1365:Gentiodelphin
1363:
1361:
1359:
1355:
1350:
1349:
1347:
1343:
1336:
1335:Malonylmalvin
1333:
1332:
1330:
1326:
1320:
1318:
1314:
1309:
1307:
1305:
1301:
1296:
1295:
1293:
1289:
1283:
1281:
1277:
1272:
1270:
1268:
1264:
1259:
1257:
1255:
1251:
1246:
1244:
1242:
1238:
1233:
1231:
1229:
1225:
1220:
1219:
1217:
1214:
1210:
1203:
1198:
1196:
1191:
1189:
1187:
1182:
1180:
1178:
1173:
1171:
1169:
1164:
1162:
1160:
1155:
1153:
1151:
1146:
1144:
1141:
1137:
1134:
1130:
1123:
1119:
1116:
1114:
1111:
1109:-galactoside)
1108:
1104:
1101:
1099:
1097:
1092:
1090:
1088:
1083:
1081:
1079:
1074:
1072:
1070:
1065:
1063:
1061:
1056:
1054:-galactoside)
1053:
1049:
1046:
1043:
1039:
1036:
1035:
1034:
1033:
1026:
1024:
1018:
1015:
1012:
1010:
1007:Peonidin 3,5-
1004:
1001:
999:-diglucoside)
998:
994:
991:
988:
985:
982:
980:
974:
971:
968:
966:
963:Cyanidin 3,5-
960:
959:
958:
957:
956:Diglucosides:
951:
948:
946:
944:
939:
937:
935:
930:
927:
923:
920:
917:
913:
910:
907:
903:
902:Chrysanthemin
900:
897:
893:
890:
889:
888:
884:
880:
876:
870:
867:
865:
862:
860:
857:
855:
852:
850:
847:
845:
842:
840:
837:
835:
832:
830:
827:
825:
822:
821:
819:
816:
812:
806:
803:
801:
798:
796:
793:
791:
790:Diosmetinidin
788:
786:
783:
781:
778:
777:
775:
773:
769:
763:
762:Robinetinidin
760:
758:
755:
753:
750:
748:
745:
743:
740:
738:
735:
733:
730:
728:
725:
723:
720:
719:
717:
713:
709:
705:
698:
693:
691:
686:
684:
679:
678:
675:
664:
660:
656:
652:
645:
642:
637:
633:
629:
625:
621:
617:
610:
607:
602:
598:
594:
590:
582:
579:
575:. Condé Nast.
574:
570:
563:
560:
557:
552:
549:
542:
537:
534:
532:
529:
527:
524:
522:
519:
518:
514:
512:
510:
506:
505:caftaric acid
502:
497:
495:
491:
486:
485:and in wine.
484:
480:
476:
472:
468:
460:
448:
441:
436:
419:
413:
409:
406:
405:
401:
399:
396:
395:
367:
364:
360:
359:
354:
345:
341:
334:
320:
310:
306:
299:
291:
287:
283:
282:
280:
270:
266:
265:
258:
254:
253:
251:
249:
246:
245:
238:
234:
233:
231:
225:
221:
220:
213:
209:
208:
206:
204:
201:
200:
196:
192:
189:
187:
185:ECHA InfoCard
182:
181:
174:
170:
169:
167:
165:
162:
161:
154:
150:
147:
143:
142:
140:
138:
135:
134:
127:
123:
122:
120:
116:
111:
110:
103:
99:
98:
96:
93:
89:
88:
83:
71:
63:
59:
49:
45:
40:
36:
31:
19:
1518:Protodelphin
1479:
1470:
1461:
1452:
1414:
1410:
1406:
1392:
1380:
1357:
1353:
1316:
1312:
1303:
1299:
1279:
1275:
1266:
1262:
1261:Petunidin 3-
1253:
1249:
1240:
1236:
1227:
1223:
1212:
1208:
1194:
1185:
1184:Petunidin 3-
1176:
1175:Petunidin 3-
1167:
1158:
1149:
1142:anthocyanins
1124:-rutinoside)
1121:
1106:
1105:(Malvidin 3-
1095:
1094:Petunidin 3-
1086:
1085:Petunidin 3-
1080:-galactoside
1077:
1076:Petunidin 3-
1071:-arabinoside
1068:
1067:Petunidin 3-
1059:
1051:
1050:(Cyanidin 3-
1044:-rutinoside)
1041:
1040:(Cyanidin 3-
1031:
1030:
1025:-diglucoside
1022:
1011:-diglucoside
1008:
996:
981:-diglucoside
978:
967:-diglucoside
964:
955:
954:
942:
941:Petunidin 3-
933:
925:
924:(Malvidin 3-
921:
915:
905:
904:(Cyanidin 3-
895:
892:Callistephin
886:
879:Anthocyanins
864:Pulchellidin
829:Capensinidin
814:
805:Tricetinidin
800:Luteolinidin
780:Apigeninidin
757:Pelargonidin
727:Aurantinidin
654:
650:
644:
619:
615:
609:
595:(18): 3578.
592:
588:
581:
572:
562:
551:
498:
487:
466:
465:
153:ChEMBL602754
146:ChEMBL403236
85:Identifiers
73:Other names
1513:Protocyanin
1425:-glucoside)
1403:Violdelphin
1352:Cyanidin 3-
1311:Peonidin 3-
1298:Malvidin 3-
1274:Peonidin 3-
1248:Malvidin 3-
1222:Cyanidin 3-
1193:Peonidin 3-
1166:Malvidin 3-
1148:Cyanidin 3-
1098:-rutinoside
1089:-rhamnoside
1062:-rhamnoside
1038:Antirrhinin
932:Peonidin 3-
928:-glucoside)
918:-glucoside)
908:-glucoside)
898:-glucoside)
887:Glucosides:
834:Europinidin
747:Fisetinidin
742:Delphinidin
657:(7): 1365.
471:anthocyanin
407:Appearance
356:Properties
191:100.027.847
1502:commelinin
1140:Acetylated
993:Pelargonin
945:-glucoside
936:-glucoside
839:Hirsutidin
795:Gesneridin
785:Columnidin
708:glucosides
543:References
526:Wine color
398:Molar mass
257:B34F52D7NB
164:ChemSpider
113:3D model (
92:CAS Number
48:IUPAC name
1118:Tulipanin
912:Myrtillin
869:Rosinidin
859:Petunidin
490:flavylium
475:glucoside
102:7228-78-6
1556:Category
1103:Primulin
961:Cyanin (
854:Peonidin
849:Malvidin
732:Cyanidin
636:12010001
515:See also
507:forming
479:malvidin
1540:Malvone
1413:-(4-(6-
1389:Petanin
1375:Nasunin
1017:Petunin
973:Delphin
440:what is
438: (
224:PubChem
1211:- and
1048:Ideain
1003:Peonin
987:Malvin
634:
483:grapes
469:is an
435:verify
432:
340:SMILES
237:443652
212:C12140
173:391785
137:ChEMBL
42:Names
28:Oenin
1356:-(di-
1213:trans
922:Oenin
573:Wired
467:Oenin
305:InChI
115:JSmol
51:3-(β-
1409:-(6-
1315:-(6-
1302:-(6-
1278:-(6-
1265:-(6-
1252:-(6-
1239:-(6-
1226:-(6-
632:PMID
248:UNII
203:KEGG
75:Enin
18:Enin
1395:-β-
1209:cis
659:doi
624:doi
597:doi
593:102
477:of
388:ClO
380:, C
274:EPA
227:CID
1558::
1215:-)
655:45
653:.
630:.
620:50
618:.
591:.
571:.
511:.
390:12
386:25
382:23
378:12
374:25
370:23
1520:)
1504:)
1500:(
1480:O
1471:O
1462:O
1453:O
1423:D
1419:D
1415:O
1411:O
1407:O
1397:D
1393:O
1385:)
1381:p
1377:(
1371:)
1367:(
1358:p
1354:O
1317:p
1313:O
1304:p
1300:O
1280:p
1276:O
1267:p
1263:O
1254:p
1250:O
1241:p
1237:O
1228:p
1224:O
1207:(
1195:O
1186:O
1177:O
1168:O
1159:O
1150:O
1122:O
1107:O
1096:O
1087:O
1078:O
1069:O
1060:O
1052:O
1042:O
1027:)
1023:O
1019:(
1013:)
1009:O
1005:(
997:O
983:)
979:O
975:(
969:)
965:O
943:O
934:O
926:O
916:O
906:O
896:O
815:O
696:e
689:t
682:v
665:.
661::
638:.
626::
603:.
599::
430:N
384:H
376:O
372:H
368:C
276:)
272:(
117:)
53:D
20:)
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