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Quebrachitol

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1955 - ACTA UNIVERSITATIS PALACKIANAE OLOMUCENSIS - TOM. VI. - HEMP AS A MEDICAMENT, Properties of isolated substances. Prof. Jan Kabelik, A brief survey of the methods of isolation and the physical and chemical properties and structures of the isolated antibacterial substances. F. Santavy & Z.
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Some new data about antiviral and related activities of seabuckthorn principals and the prospects of their use. Shipulina L.D., All-Russian Research Institute of Medicinal and Aromatic Plants, Moscow, Russia
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Total synthesis of antibiotic (−)-oudemansin X utilizing L-quebrachitol as a chiral pool. Chida N., Yamada K. and Ogawa S., Chemistry Letters, 1992, no4, pp. 687-690
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Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials. For example, its conversion into antifungal
418:. The substance was tested as a sweetening agent for diabetics in 1933. It shows a sweetening property half of that of sucrose but induces colic or 588:
Kiddle, James J. (1995). "Quebrachitol: A Versatile Building Block in the Construction of Naturally Occurring Bioactive Materials".
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Díaz, Martina; González, Andrés; Castro-Gamboa, Ian; Gonzalez, David; Rossini, Carmen (13 October 2008).
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InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m0/s1
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Except where otherwise noted, data are given for materials in their
452:"First record of l-quebrachitol in Allophylus edulis (Sapindaceae)" 104: 94: 298:
190 to 198 °C (374 to 388 °F; 463 to 471 K)
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at concentration used to render the food palatable.
379:and in the serum left after the coagulation of the 43:(1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol 651:: CS1 maint: bot: original URL status unknown ( 169: 633:. Archived from the original on October 3, 2012 80: 8: 631:"Quebrachitol on the Sigma-Aldrich website" 369:is a naturally occurring optically active 144: 18: 564: 189: 489:van Alphen, Jan (1951). "Quebrachitol". 442: 234: 209: 644: 491:Industrial & Engineering Chemistry 373:, a cyclic polyol. It can be found in 216:Key: DSCFFEYYQKSRSV-FIZWYUIZSA-N 124: 7: 160: 539:McCance, RA; Lawrence, RD (1933). 14: 332: 25: 328:(at 25 °C , 100 kPa). 1: 468:10.1016/j.carres.2008.07.014 686: 385:latex in the operation of 288:White to off-white powder 280:194.18 g/mol 412:in 1887 from the bark of 408:It was first isolated by 322: 245: 225: 200: 64: 59:2-0-methyl-chiro-inositol 48: 38: 33: 24: 415:Aspidosperma quebracho 389:. It is also found in 456:Carbohydrate Research 427:(E)-β-methoxyacrylate 57:2-O-methyl-l-inositol 602:10.1021/cr00038a016 503:10.1021/ie50493a041 305:Solubility in water 21: 382:Hevea brasiliensis 355:Infobox references 316:dimethyl formamide 19: 557:10.1042/bj0270986 462:(15): 2699–2700. 398:Paullinia pinnata 376:Allophylus edulis 363:Chemical compound 361: 360: 237:CO1((((1O)O)O)O)O 106:Interactive image 16:Chemical compound 677: 656: 650: 642: 640: 638: 617: 612: 606: 605: 596:(6): 2189–2202. 590:Chemical Reviews 585: 579: 578: 568: 536: 530: 525: 519: 513: 507: 506: 486: 480: 479: 447: 345: 339: 336: 335: 253:Chemical formula 193: 173: 162: 148: 128: 108: 84: 55:(-)-Quebrachitol 29: 22: 685: 684: 680: 679: 678: 676: 675: 674: 660: 659: 643: 636: 634: 629: 626: 621: 620: 613: 609: 587: 586: 582: 538: 537: 533: 526: 522: 514: 510: 488: 487: 483: 449: 448: 444: 439: 433:has been made. 392:Cannabis sativa 364: 357: 352: 351: 350:  ?) 341: 337: 333: 329: 307: 269: 265: 261: 255: 241: 238: 233: 232: 221: 218: 217: 214: 208: 207: 196: 176: 163: 151: 131: 111: 98: 87: 74: 60: 58: 56: 54: 52: 44: 17: 12: 11: 5: 683: 681: 673: 672: 662: 661: 658: 657: 625: 624:External links 622: 619: 618: 607: 580: 531: 520: 508: 481: 441: 440: 438: 435: 387:rubber tapping 362: 359: 358: 353: 331: 330: 326:standard state 323: 320: 319: 308: 303: 300: 299: 296: 290: 289: 286: 282: 281: 278: 272: 271: 267: 263: 259: 256: 251: 248: 247: 243: 242: 240: 239: 236: 228: 227: 226: 223: 222: 220: 219: 215: 212: 211: 203: 202: 201: 198: 197: 195: 194: 186: 184: 178: 177: 175: 174: 166: 164: 156: 153: 152: 150: 149: 141: 139: 133: 132: 130: 129: 121: 119: 113: 112: 110: 109: 101: 99: 92: 89: 88: 86: 85: 77: 75: 70: 67: 66: 62: 61: 53:L-Quebrachitol 50: 46: 45: 42: 36: 35: 31: 30: 15: 13: 10: 9: 6: 4: 3: 2: 682: 671: 668: 667: 665: 654: 648: 637:September 19, 632: 628: 627: 623: 616: 611: 608: 603: 599: 595: 591: 584: 581: 576: 572: 567: 562: 558: 554: 550: 546: 542: 535: 532: 529: 524: 521: 518: 512: 509: 504: 500: 496: 492: 485: 482: 477: 473: 469: 465: 461: 457: 453: 446: 443: 436: 434: 432: 428: 423: 421: 417: 416: 411: 406: 404: 400: 399: 394: 393: 388: 384: 383: 378: 377: 372: 368: 356: 349: 344: 327: 321: 317: 313: 309: 306: 302: 301: 297: 295: 294:Melting point 292: 291: 287: 284: 283: 279: 277: 274: 273: 257: 254: 250: 249: 244: 235: 231: 224: 210: 206: 199: 192: 188: 187: 185: 183: 180: 179: 172: 168: 167: 165: 159: 155: 154: 147: 143: 142: 140: 138: 135: 134: 127: 123: 122: 120: 118: 115: 114: 107: 103: 102: 100: 96: 91: 90: 83: 79: 78: 76: 73: 69: 68: 63: 47: 41: 37: 32: 28: 23: 20:quebrachitol 635:. Retrieved 610: 593: 589: 583: 551:(4): 986–9. 548: 544: 534: 523: 511: 494: 490: 484: 459: 455: 445: 431:oudemansin X 424: 413: 407: 403:seabuckthorn 396: 390: 380: 374: 367:Quebrachitol 366: 365: 126:ChEMBL501109 65:Identifiers 51:Quebrachitol 49:Other names 497:: 141–145. 318:, or water 310:Soluble in 285:Appearance 246:Properties 437:References 276:Molar mass 191:9W4JLQ7I4W 137:ChemSpider 93:3D model ( 72:CAS Number 40:IUPAC name 670:Cyclitols 545:Biochem J 420:diarrhoea 664:Category 647:cite web 575:16745234 476:18715552 371:cyclitol 146:10254652 82:642-38-6 566:1252976 401:and in 348:what is 346: ( 270: 158:PubChem 573:  563:  517:Krejci 474:  410:Tanret 343:verify 340:  230:SMILES 171:151108 117:ChEMBL 34:Names 395:, in 205:InChI 95:JSmol 653:link 639:2016 571:PMID 472:PMID 312:DMSO 182:UNII 598:doi 561:PMC 553:doi 499:doi 464:doi 460:343 161:CID 666:: 649:}} 645:{{ 594:95 592:. 569:. 559:. 549:27 547:. 543:. 495:43 493:. 470:. 458:. 454:. 429:, 405:. 314:, 264:14 655:) 641:. 604:. 600:: 577:. 555:: 505:. 501:: 478:. 466:: 338:N 268:6 266:O 262:H 260:7 258:C 97:)

Index

Chemical structure of quebrachitol
IUPAC name
CAS Number
642-38-6
JSmol
Interactive image
ChEMBL
ChEMBL501109
ChemSpider
10254652
PubChem
151108
UNII
9W4JLQ7I4W
InChI
SMILES
Chemical formula
Molar mass
Melting point
Solubility in water
DMSO
dimethyl formamide
standard state
verify
what is
Infobox references
cyclitol
Allophylus edulis
Hevea brasiliensis
rubber tapping

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