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Procyanidin B3

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Benavides, Angelyne; Montoro, Paola; Bassarello, Carla; Piacente, Sonia; Pizza, Cosimo (2006). "Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali–quantitative analysis".
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InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1
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Delcour, Jan. A.; Ferreira, Daneel; Roux, David G. (1983). "Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins".
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Kamimura, A; Takahashi, T (2002). "Procyanidin B-3, isolated from barley and identified as a hair-growth stimulant, has the potential to counteract inhibitory regulation by TGF-beta1".
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Quinde-Axtell, Zory; Baik, Byung-Kee (2006). "Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration".
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condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-- and -bi- (procyanidins B3,
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Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer
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Infante, Rodrigo; Contador, Loreto; Rubio, Pía; Aros, Danilo; Peña-Neira, Álvaro (2011).
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O1Cc2c(O)cc(O)c(3(O)(Oc4cc(O)cc(O)c34)c3ccc(O)c(O)c3)c2O1c1ccc(O)c(O)c1
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Except where otherwise noted, data are given for materials in their
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C. Dallas, J.M. Ricardo-Da-Silva and Olga Laureano (1995).
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Journal of the Chemical Society, Perkin Transactions 1
71:)-2,2′-Bis(3,4-dihydroxyphenyl)-3,3′,4,4′-tetrahydro-2 458: 1053:(epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin) 897: 865:Journal of Pharmaceutical and Biomedical Analysis 773: 730: 1174: 1047:(epicatechin-(4β→8)-epicatechin-(4β→6)-catechin) 255: 643:Molar equivalents of synthetic (2R,3S,4R or S)- 109: 532: 1157: 933: 1164: 1150: 1059:(catechin-(4α→8)-catechin-(4α→8)-catechin) 940: 926: 776:Journal of Agricultural and Food Chemistry 726: 724: 308: 215: 193: 947: 846: 275: 835:Chilean Journal of Agricultural Research 808: 721: 304: 1175: 802: 600: 593:. Procyanidin B3 is a catechin dimer ( 206: 921: 638: 336:Key: XFZJEEAOWLFHDH-AVFWISQGSA-N 173: 153: 1116: 246: 13: 14: 1199: 745:10.1034/j.1600-0625.2002.110606.x 626: 1120: 605:It can be found in red wine, in 552: 428: 22: 1040:(ent-Epicatechin(4α→8)catechin) 848:10.4067/S0718-58392011000300016 548:(at 25 °C , 100 kPa). 891: 855: 819: 767: 681: 1: 674: 655:) the all-trans-- and -tri- ( 1136:. You can help Knowledge by 631:It has been identified as a 7: 662: 10: 1204: 1115: 877:10.1016/j.jpba.2005.10.004 703:(1): 51–56. Archived from 400:578.52 g/mol 1072: 992: 956: 542: 409: 404: 365: 345: 320: 93: 85: 45: 35: 30: 21: 994:B type proanthocyanidins 958:A-type proanthocyanidins 733:Experimental Dermatology 669:Phenolic content in wine 475:Precautionary statements 1188:Aromatic compound stubs 591:B type proanthocyanidin 1128:This article about an 623:, the Huanarpo Macho. 79:--3,3′,5,5′,7,7′-hexol 809:Delcour, Jan (1985). 633:hair-growth stimulant 47:Systematic IUPAC name 908:10.1039/P19830001711 601:Natural occurrences 597:-(4α→8)-catechin). 18: 1183:Procyanidin dimers 639:Chemical synthesis 620:Jatropha macrantha 575:Infobox references 16: 1145: 1144: 1110: 1109: 1062:Tetramers : 788:10.1021/jf060974w 583:Chemical compound 581: 580: 453:Hazard statements 289:CompTox Dashboard 135:Interactive image 1195: 1166: 1159: 1152: 1124: 1117: 942: 935: 928: 919: 918: 912: 911: 895: 889: 888: 859: 853: 852: 850: 832: 823: 817: 816: 806: 800: 799: 771: 765: 764: 728: 719: 718: 716: 715: 709: 694: 685: 565: 559: 556: 555: 538: 534: 530: 526: 522: 518: 514: 510: 506: 502: 498: 494: 490: 486: 482: 468: 464: 460: 432: 373:Chemical formula 313: 312: 297: 295: 279: 259: 248: 227: 219: 208: 197: 177: 157: 137: 113: 26: 19: 15: 1203: 1202: 1198: 1197: 1196: 1194: 1193: 1192: 1173: 1172: 1171: 1170: 1113: 1111: 1106: 1068: 1064:Cinnamtannin A2 988: 978:Cinnamtannin B1 952: 946: 916: 915: 896: 892: 860: 856: 830: 824: 820: 807: 803: 782:(26): 9978–84. 772: 768: 729: 722: 713: 711: 707: 692: 686: 682: 677: 665: 641: 629: 603: 584: 577: 572: 571: 570:  ?) 561: 557: 553: 549: 477: 455: 441: 425: 389: 385: 381: 375: 361: 358: 353: 352: 341: 338: 337: 334: 328: 327: 316: 298: 291: 282: 262: 249: 237: 200: 180: 160: 140: 127: 116: 103: 89: 81: 80: 41: 17:Procyanidin B3 12: 11: 5: 1201: 1191: 1190: 1185: 1169: 1168: 1161: 1154: 1146: 1143: 1142: 1132:compound is a 1125: 1108: 1107: 1105: 1104: 1103: 1102: 1100:Arecatannin C1 1097: 1095:Arecatannin B2 1092: 1090:Arecatannin A3 1087: 1085:Arecatannin A1 1076: 1074: 1070: 1069: 1067: 1066: 1060: 1057:Procyanidin C2 1054: 1051:Procyanidin C1 1048: 1045:Arecatannin B1 1041: 1035: 1030: 1025: 1020: 1015: 1010: 1005: 1003:Procyanidin B1 1001:Dimers : 998: 996: 990: 989: 987: 986: 984:Arecatannin A2 980: 974: 969: 967:Procyanidin A1 965:Dimers : 962: 960: 954: 953: 945: 944: 937: 930: 922: 914: 913: 890: 854: 841:(3): 445–451. 818: 801: 766: 720: 679: 678: 676: 673: 672: 671: 664: 661: 657:procyanidin C2 640: 637: 628: 627:Health effects 625: 602: 599: 587:Procyanidin B3 582: 579: 578: 573: 551: 550: 546:standard state 543: 540: 539: 505:P305+P351+P338 478: 473: 470: 469: 456: 451: 448: 447: 442: 437: 434: 433: 426: 421: 418: 417: 407: 406: 402: 401: 398: 392: 391: 387: 383: 379: 376: 371: 368: 367: 363: 362: 360: 359: 356: 348: 347: 346: 343: 342: 340: 339: 335: 332: 331: 323: 322: 321: 318: 317: 315: 314: 306:DTXSID60178193 301: 299: 287: 284: 283: 281: 280: 272: 270: 264: 263: 261: 260: 252: 250: 242: 239: 238: 236: 235: 231: 229: 221: 220: 210: 202: 201: 199: 198: 190: 188: 182: 181: 179: 178: 170: 168: 162: 161: 159: 158: 150: 148: 142: 141: 139: 138: 130: 128: 121: 118: 117: 115: 114: 106: 104: 99: 96: 95: 91: 90: 88:Procyanidin B3 87: 83: 82: 50: 49: 43: 42: 39: 33: 32: 28: 27: 9: 6: 4: 3: 2: 1200: 1189: 1186: 1184: 1181: 1180: 1178: 1167: 1162: 1160: 1155: 1153: 1148: 1147: 1141: 1139: 1135: 1131: 1126: 1123: 1119: 1118: 1114: 1101: 1098: 1096: 1093: 1091: 1088: 1086: 1083: 1082: 1081: 1078: 1077: 1075: 1071: 1065: 1061: 1058: 1055: 1052: 1049: 1046: 1042: 1039: 1036: 1034: 1031: 1029: 1026: 1024: 1021: 1019: 1016: 1014: 1011: 1009: 1006: 1004: 1000: 999: 997: 995: 991: 985: 981: 979: 975: 973: 970: 968: 964: 963: 961: 959: 955: 951: 943: 938: 936: 931: 929: 924: 923: 920: 909: 905: 901: 894: 886: 882: 878: 874: 871:(3): 639–47. 870: 866: 858: 849: 844: 840: 836: 829: 822: 814: 813: 805: 797: 793: 789: 785: 781: 777: 770: 762: 758: 754: 750: 746: 742: 739:(6): 532–41. 738: 734: 727: 725: 710:on 2013-12-03 706: 702: 698: 691: 684: 680: 670: 667: 666: 660: 659:and isomer). 658: 654: 650: 646: 645:leucocyanidin 636: 634: 624: 622: 621: 616: 612: 608: 598: 596: 592: 588: 576: 569: 564: 547: 541: 479: 476: 472: 471: 457: 454: 450: 449: 446: 443: 440: 436: 435: 431: 427: 424: 420: 419: 415: 413: 408: 403: 399: 397: 394: 393: 377: 374: 370: 369: 364: 355: 354: 351: 344: 330: 329: 326: 319: 311: 307: 303: 302: 300: 290: 286: 285: 278: 274: 273: 271: 269: 266: 265: 258: 254: 253: 251: 245: 241: 240: 233: 232: 230: 228: 223: 222: 218: 214: 211: 209: 207:ECHA InfoCard 204: 203: 196: 192: 191: 189: 187: 184: 183: 176: 172: 171: 169: 167: 164: 163: 156: 152: 151: 149: 147: 144: 143: 136: 132: 131: 129: 125: 120: 119: 112: 108: 107: 105: 102: 98: 97: 92: 84: 78: 74: 70: 66: 62: 58: 54: 48: 44: 38: 34: 29: 25: 20: 1138:expanding it 1127: 1112: 1080:Arecatannins 1012: 950:procyanidins 899: 893: 868: 864: 857: 838: 834: 821: 811: 804: 779: 775: 769: 736: 732: 712:. Retrieved 705:the original 700: 696: 683: 642: 630: 618: 604: 586: 585: 444: 411: 175:ChEMBL501490 94:Identifiers 86:Other names 76: 72: 68: 64: 60: 56: 52: 982:Tetramers: 439:Signal word 366:Properties 213:100.150.578 155:CHEBI:75630 1177:Categories 714:2013-06-24 675:References 423:Pictograms 396:Molar mass 277:2TC1A0KEAQ 186:ChemSpider 122:3D model ( 111:23567-23-9 101:CAS Number 37:IUPAC name 1043:Trimers: 948:Types of 529:P403+P233 521:P337+P313 517:P332+P313 501:P304+P340 497:P302+P352 414:labelling 234:621-754-2 226:EC Number 1130:aromatic 976:Trimers: 902:: 1711. 885:16300918 796:17177530 761:39454993 753:12473061 663:See also 649:catechin 647:and (+)- 595:catechin 405:Hazards 568:what is 566: ( 445:Warning 390: 244:PubChem 40:-(4→8)- 883:  794:  759:  751:  617:or in 607:barley 563:verify 560:  350:SMILES 257:146798 195:129476 166:ChEMBL 31:Names 1073:Types 831:(PDF) 757:S2CID 708:(PDF) 697:Vitis 693:(PDF) 615:peach 613:, in 609:, in 589:is a 325:InChI 146:ChEBI 124:JSmol 1134:stub 881:PMID 792:PMID 749:PMID 611:beer 537:P501 533:P405 525:P362 513:P321 509:P312 493:P280 489:P271 485:P264 481:P261 467:H335 463:H319 459:H315 268:UNII 904:doi 873:doi 843:doi 784:doi 741:doi 412:GHS 294:EPA 247:CID 75:,2′ 63:,3′ 55:,2′ 1179:: 1033:B8 1028:B6 1023:B5 1018:B4 1013:B3 1008:B2 972:A2 879:. 869:40 867:. 839:71 837:. 833:. 790:. 780:54 778:. 755:. 747:. 737:11 735:. 723:^ 701:34 699:. 695:. 653:B6 635:. 535:, 531:, 527:, 523:, 519:, 515:, 511:, 507:, 503:, 499:, 495:, 491:, 487:, 483:, 465:, 461:, 416:: 388:12 384:26 380:30 67:,4 59:,3 51:(2 1165:e 1158:t 1151:v 1140:. 1038:D 941:e 934:t 927:v 910:. 906:: 887:. 875:: 851:. 845:: 815:. 798:. 786:: 763:. 743:: 717:. 558:Y 386:O 382:H 378:C 296:) 292:( 126:) 77:H 73:H 69:S 65:S 61:S 57:R 53:R

Index

Chemical structure of procyanidin B3
IUPAC name
Systematic IUPAC name
CAS Number
23567-23-9
JSmol
Interactive image
ChEBI
CHEBI:75630
ChEMBL
ChEMBL501490
ChemSpider
129476
ECHA InfoCard
100.150.578
Edit this at Wikidata
EC Number
PubChem
146798
UNII
2TC1A0KEAQ
CompTox Dashboard
DTXSID60178193
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
GHS labelling
Pictograms

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