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Chalcone

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Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation. Some 2′-amino chalcones have been studied as potential antitumor agents. Chalcones are of interest in
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Song, Dong-mee; Jung, Kyoung-Hoon; Moon, Ji-hye; Shin, Dong-Myung (2003). "Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display".
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Xia, Yi; Yang, Zheng-Yu; Xia, Peng; Bastow, Kenneth F.; Nakanishi, Yuka; Lee, Kuo-Hsiung (2000). "Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation".
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Santos, Mariana B.; Pinhanelli, Vitor C.; Garcia, Mayara A.R.; Silva, Gabriel; Baek, Seung J.; França, Suzelei C.; Fachin, Ana L.; Marins, Mozart; Regasini, Luis O. (2017).
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Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar; Asati, Vivek (2017). "Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives".
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Tomás-Barberán, Francisco A.; Clifford, Michael N. (2000). "Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden".
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This reaction, which can be carried out without any solvent, is so reliable that it is often given as an example of
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Zhuang, Chunlin; Zhang, Wen; Sheng, Chunquan; Zhang, Wannian; Xing, Chengguo; Miao, Zhenyuan (28 June 2017).
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Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of
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Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
550:. They are widely known bioactive substances, fluorescent materials, and chemical intermediates. 464: 1253: 978: 864: 571: 281: 52: 217: 8: 722: 661: 644: 640: 579: 148: 131: 1186: 1143: 982: 868: 314: 239: 197: 141: 1210: 1167: 919: 894: 603: 591: 17: 1052: 1017: 876: 1214: 1202: 1171: 1159: 1124: 1116: 1064: 1056: 1021: 924: 808: 688: 678: 575: 546:. A variety of important biological compounds are known collectively as chalcones or 1231: 1194: 1151: 1106: 1098: 1048: 1013: 986: 951: 914: 906: 872: 837: 800: 673: 523: 387: 261: 1263: 1238: 1102: 627: 910: 804: 704: 683: 587: 478: 842:
10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B
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Chalcones have two absorption maxima at 280 nm and 340 nm.
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InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H
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Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04).
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Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04).
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Except where otherwise noted, data are given for materials in their
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InChI=1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H
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Palleros, Daniel R (2004). "Solvent-Free Synthesis of Chalcones".
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E. P. Kohler, H. M. Chadwell (1922). "Benzalacetophenone".
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345 to 348 °C (653 to 658 °F; 618 to 621 K)
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of these compounds. The enzyme is found in all "higher" (
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55 to 57 °C (131 to 135 °F; 328 to 330 K)
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synthesized in plants as 73:)-1,3-Diphenylprop-2-en-1-one 1103:10.1016/j.ejmech.2017.06.049 630:in undergraduate education. 7: 911:10.1021/acs.chemrev.7b00020 805:10.1039/9781849733069-FP001 750: 10: 1280: 15: 757:Juliá–Colonna epoxidation 735:Uses in organic chemistry 582:, is responsible for the 475: 380: 360: 325: 124: 79: 63: 51: 46: 37: 28: 16:For the butterflies, see 1232:Chalcone on reference.md 956:10.15227/orgsyn.002.0001 372:O=C(C=Cc1ccccc1)c2ccccc2 650: 590:) and several "lower" ( 465:Magnetic susceptibility 84:Benzylideneacetophenone 634:Potential pharmacology 544:α,β-unsaturated ketone 799:. 2014. p. 722. 572:secondary metabolites 65:Systematic IUPAC name 723:corrosion inhibitors 598:Laboratory synthesis 93:-phenylacrylophenone 86:Phenyl styryl ketone 53:Preferred IUPAC name 983:2004JChEd..81.1345P 869:2003OptMa..21..667S 662:medicinal chemistry 645:privileged scaffold 641:medicinal chemistry 580:polyketide synthase 554:Chemical properties 420: g·mol 25: 1237:2020-09-25 at the 991:10.1021/ed081p1345 713:chemical scaffolds 689:antimalarial drugs 679:antidiabetic drugs 604:aldol condensation 508:Infobox references 428:pale yellow solid 88:benzalacetophenone 23: 18:Chalcone (skipper) 1199:10.1002/jhet.4617 1156:10.1002/jhet.4617 1012:(28): 3146–3169. 944:Organic Syntheses 905:(12): 7762–7810. 857:Optical Materials 814:978-0-85404-182-4 674:Anticancer agents 576:chalcone synthase 516:Chemical compound 514: 513: 471:-125.7·10 cm/mol 294:CompTox Dashboard 178:Interactive image 119:-benzoylethylene. 1271: 1259:Phenyl compounds 1219: 1218: 1182: 1176: 1175: 1139: 1133: 1132: 1114: 1088: 1079: 1073: 1072: 1036: 1030: 1029: 1001: 995: 994: 966: 960: 959: 939: 933: 932: 922: 899:Chemical Reviews 890: 881: 880: 852: 846: 845: 836:(7): 1073–1080. 825: 819: 818: 791:"Front Matter". 788: 782: 778:, 11th Edition, 773: 622: 524:organic compound 498: 492: 489: 488: 419: 407: 401: 395: 388:Chemical formula 318: 317: 302: 300: 284: 264: 253: 242: 231: 220: 200: 180: 151: 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Cambridge: 794: 787: 781: 777: 772: 768: 758: 755: 754: 748: 746: 742: 729: 726: 724: 721: 719: 718:metal sensors 716: 714: 711: 708: 706: 703: 702: 701: 690: 687: 685: 682: 680: 677: 675: 672: 670: 667: 666: 665: 663: 648: 646: 642: 631: 629: 621: 617: 616: 615: 613: 609: 605: 595: 593: 589: 585: 581: 578:, a type III 577: 574:. The enzyme 573: 569: 559: 551: 549: 545: 525: 521: 509: 502: 497: 480: 474: 470: 466: 462: 461: 457: 455: 454:Boiling point 452: 451: 447: 445: 444:Melting point 442: 441: 437: 435: 432: 431: 427: 424: 423: 416: 414: 411: 410: 392: 389: 385: 384: 379: 370: 369: 366: 359: 345: 335: 334: 331: 324: 316: 312: 308: 307: 305: 295: 291: 290: 283: 279: 278: 276: 274: 271: 270: 263: 259: 258: 256: 250: 246: 245: 241: 237: 234: 232: 230:ECHA InfoCard 227: 226: 219: 215: 214: 212: 210: 207: 206: 199: 195: 194: 192: 190: 187: 186: 179: 175: 174: 172: 168: 163: 162: 155: 150: 146: 143: 139: 138: 136: 133: 129: 128: 123: 118: 114: 109: 105: 101: 97: 92: 78: 72: 66: 62: 54: 50: 45: 41: 36: 32: 27: 19: 1190: 1180: 1147: 1137: 1112:11449/174929 1094: 1090: 1077: 1044: 1040: 1034: 1009: 1005: 999: 974: 970: 964: 947: 943: 937: 902: 898: 860: 856: 850: 833: 829: 823: 792: 786: 779: 775: 771: 738: 699: 669:antioxidants 659: 637: 625: 612:acetophenone 608:benzaldehyde 601: 592:non-vascular 584:biosynthesis 565: 562:Biosynthesis 557: 519: 518: 153: 125:Identifiers 116: 112: 107: 103: 99: 95: 90: 80:Other names 70: 1254:Chalconoids 1097:: 884–889. 977:(9): 1345. 776:Merck Index 710:fluorescent 568:chalconoids 548:chalconoids 542:. It is an 438:1.071 g/cm 425:Appearance 381:Properties 236:100.002.119 198:CHEBI:27618 156:)-Chalcone) 1248:Categories 763:References 594:) plants. 534:C(O)CH=CHC 413:Molar mass 282:5S5A2Q39HX 209:ChemSpider 165:3D model ( 132:CAS Number 110:-propylene 106:-diphenyl- 1215:255212828 1207:0022-152X 1172:255212828 1164:0022-152X 1121:0223-5234 1061:0960-894X 741:pyrazoles 691:and more. 24:Chalcone 1235:Archived 1129:28738308 1069:10782667 1026:28914193 929:28488435 751:See also 606:between 588:vascular 520:Chalcone 467:(χ) 152: (( 149:614-47-1 115:-phenyl- 82:Chalkone 57:Chalcone 979:Bibcode 920:6131713 865:Bibcode 745:aurones 522:is the 501:what is 499: ( 434:Density 418:208.260 249:PubChem 142:94-41-7 1264:Enones 1213:  1205:  1170:  1162:  1127:  1119:  1067:  1059:  1024:  927:  917:  811:  496:verify 493:  365:SMILES 262:637760 47:Names 1211:S2CID 1168:S2CID 1087:(PDF) 950:: 1. 330:InChI 189:ChEBI 167:JSmol 98:-oxo- 1203:ISSN 1160:ISSN 1125:PMID 1117:ISSN 1065:PMID 1057:ISSN 1022:PMID 925:PMID 809:ISBN 780:2028 743:and 651:Uses 610:and 273:UNII 218:6921 1195:doi 1152:doi 1107:hdl 1099:doi 1095:138 1049:doi 1014:doi 987:doi 952:doi 915:PMC 907:doi 903:117 873:doi 838:doi 801:doi 660:In 299:EPA 252:CID 1250:: 1209:. 1201:. 1189:. 1166:. 1158:. 1146:. 1123:. 1115:. 1105:. 1093:. 1089:. 1063:. 1055:. 1045:10 1043:. 1020:. 1010:17 1008:. 985:. 975:81 973:. 946:. 923:. 913:. 901:. 897:. 885:^ 871:. 861:21 859:. 834:80 832:. 807:. 747:. 647:. 614:. 403:12 397:15 69:(2 1217:. 1197:: 1174:. 1154:: 1131:. 1109:: 1101:: 1071:. 1051:: 1028:. 1016:: 993:. 989:: 981:: 958:. 954:: 948:2 931:. 909:: 879:. 875:: 867:: 844:. 840:: 817:. 803:: 730:. 540:5 538:H 536:6 532:5 530:H 528:6 526:C 491:N 406:O 400:H 394:C 301:) 297:( 169:) 154:E 117:β 113:α 108:α 104:γ 102:, 100:α 96:γ 91:β 71:E 20:.

Index

Chalcone (skipper)
Skeletal formula of chalcone
Ball-and-stick model of the chalcone molecule
Preferred IUPAC name
Systematic IUPAC name
CAS Number
94-41-7
614-47-1
JSmol
Interactive image
ChEBI
CHEBI:27618
ChemSpider
6921
ECHA InfoCard
100.002.119
Edit this at Wikidata
PubChem
637760
UNII
5S5A2Q39HX
CompTox Dashboard
DTXSID20873536
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Density
Melting point

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