475:
138:. He manually separated the crystals of a mixture, starting from an aqueous solution of the sodium ammonium salt of racemate tartaric acid. Pasteur benefited from the fact that ammonium tartrate salt gives enantiomeric crystals with distinct crystal forms (at 77 °F). Reasoning from the macroscopic scale down to the molecular, he reckoned that the molecules had to have non-superimposable mirror images. A sample with only a single enantiomer is an
595:. The (R) enantiomer of thalidomide is effective against morning sickness, while the (S) enantiomer is teratogenic, causing birth defects. Since the drug racemizes, the drug cannot be considered safe for use by women of child-bearing age, and its use is tightly controlled when used for treating other illness.
384:
When there is no big difference in affinity between the same and opposite enantiomers, then in contrast to the racemic compound and the conglomerate, the two enantiomers will coexist in an unordered manner in the crystal lattice. Addition of a small amount of one enantiomer changes the melting point
363:
than for the same enantiomer, the substance forms a single crystalline phase in which the two enantiomers are present in an ordered 1:1 ratio in the elementary cell. Adding a small amount of one enantiomer to the racemic compound decreases the melting point. But the pure enantiomer can have a higher
297:
In contrast to the two pure enantiomers, which have identical physical properties except for the direction of rotation of plane-polarized light, a racemate sometimes has different properties from either of the pure enantiomers. Different melting points are most common, but different solubilities and
447:
or starting material), a chemical reaction that makes a chiral product will always yield a racemate. That can make the synthesis of a racemate cheaper and easier than making the pure enantiomer, because it does not require special conditions. This fact also leads to the question of how biological
393:
A quasiracemate is a co-crystal of two similar but distinct compounds, one of which is left-handed and the other right-handed. Although chemically different, they are sterically similar (isosteric) and are still able to form a racemic crystalline phase. One of the first such racemates studied, by
305:
Pharmaceuticals may be available as a racemate or as the pure enantiomer, which might have different potencies. Because biological systems have many chiral asymmetries, pure enantiomers frequently have very different biological effects; examples include
556:. This means that preparing a pure enantiomer for medication is largely pointless. However, sometimes samples containing pure enantiomers may be made and sold at a higher cost in cases where the use requires specifically one isomer (e.g., for a
337:
If the molecules of the substance have a much greater affinity for the same enantiomer than for the opposite one, a mechanical mixture of enantiomerically pure crystals will result. The mixture of enantiomerically pure R and S crystals forms a
1015:
de Jesus, Soraya
Machado; Santana, Rafael Santos; Leite, Silvana Nair (2 January 2022). "Comparative analysis of the use and control of thalidomide in Brazil and different countries: is it possible to say there is safety?".
346:
of the conglomerate is always lower than that of the pure enantiomer. Addition of a small amount of one enantiomer to the conglomerate increases the melting point. Roughly 10% of racemic chiral compounds crystallize as
1105:
Brock, Carolyn Pratt; Schweizer, W. Bernd; Dunitz, Jack D. (December 1991). "On the validity of
Wallach's rule: on the density and stability of racemic crystals compared with their chiral counterparts".
286:
light. Although the two enantiomers rotate plane-polarized light in opposite directions, the rotations cancel each other out because they are present in equal amounts of negative (-) counterclockwise (
471:
intermediate) acting as an electrophile. The nucleophile will have a 50% probability of 'hitting' either of the two sides of the planar grouping, thus producing a racemic mixture:
617:
drug that is less centrally-acting and more peripherally-acting. Methedrine during the 20th century was a 50:50 racemic mixture of both methamphetamine isomers (levo and dextro).
410:-shape with the central part consisting of ammonium (+)-bitartrate, whereas the outer parts are a quasiracemic mixture of ammonium (+)-bitartrate and ammonium (−)-bimalate.
1285:
1290:
496:
are chiral, and the enantiomers have different effects on biological entities. They can be sold as one enantiomer or as a racemic mixture. Examples include
568:. Moving from a racemic drug to a chiral specific drug may be done for a better safety profile or an improved therapeutic index. This process is called
1721:
1151:
162:, meaning a bunch of grapes. This acid, when naturally produced in grapes, is only the right-handed version of the molecule, better known as
1060:
1681:
1397:
1740:
1078:
Wallach, O. (1895). "Zur
Kenntniss der Terpene und der ätherischen Oele" [On the knowledge of terpenes and essential oils].
910:
Wheeler, Kraig A.; Grove, Rebecca C.; Davis, Raymond E.; Kassel, W. Scott (January 2008). "Rediscovering
Pasteur's Quasiracemates".
532:
was a racemic mixture, and isolated dextroamphetamine was later introduced to the market as
Dexedrine. The prescription analgesic
851:
742:
587:
While often only one enantiomer of the drug may be active, there are cases in which the other enantiomer is harmful, like
528:
and amphetamine, with the dextro isomer of amphetamine saccharate and D/L-amphetamine aspartate monohydrate. The original
372:), in which the crystal itself has handedness (is enantiomorphic), despite containing both enantiomorphs in a 1:1 ratio.
1144:
1323:
323:
1596:
114:
molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates.
606:
1809:
764:. Department of Chemistry, Queen Mary University of London: Blackwell Scientific Publications. pp. 8, 11.
1763:
1390:
1308:
1137:
1318:
1701:
1577:
1814:
1499:
1161:
1804:
1280:
945:
Agranat, Israel; Wainschtein, Silvya R. (March 2010). "The strategy of enantiomer patents of drugs".
1799:
1780:
1383:
1206:
676:
1446:
666:
609:. This is the right-handed isomer of methamphetamine. The left-handed isomer of methamphetamine,
369:
365:
1672:
1437:
661:
1619:
1559:
1344:
1258:
1175:
875:
Fábián, László; Brock, Carolyn Pratt (1 February 2010). "A list of organic kryptoracemates".
651:
634:
614:
436:
111:
213:
may be used), indicating an equal (1:1) mixture of dextro and levo isomers. Also the prefix
1623:
1354:
1339:
1190:
283:
980:
Ameredes, Bill T.; Calhoun, William J. (November 2006). "(R)-Albuterol for Asthma: Pro ".
419:
The separation of a racemate into its components, the individual enantiomers, is called a
8:
1252:
1129:
610:
103:
512:. A well known drug that has different effects depending on its ratio of enantiomers is
474:
1534:
1313:
1211:
1041:
815:
798:
734:
697:
637:
counterparts. This rule has been substantiated by crystallographic database analysis.
455:
The reagents of, and the reactions that produce, racemic mixtures are said to be "not
1300:
1045:
1033:
997:
962:
927:
892:
857:
847:
738:
655:
525:
420:
802:
1349:
1275:
1185:
1115:
1087:
1025:
989:
954:
919:
884:
828:
788:
730:
487:
275:
190:, means 'grape elder', so called because its berries grow in a grape-like cluster.
34:
1029:
467:. A frequent scenario is that of a planar species (such as an sp carbon atom or a
364:
or lower melting point than the compound. A special case of racemic compounds are
1406:
1359:
1227:
1201:
958:
702:
598:
464:
460:
339:
311:
1642:
581:
557:
493:
456:
424:
291:
179:
888:
1793:
1242:
1091:
646:
573:
449:
399:
395:
343:
299:
175:
166:. In many Germanic languages racemic acid is called “grape acid” e.g. German
163:
135:
127:
793:
776:
1472:
1364:
1237:
1180:
1037:
1001:
966:
931:
923:
896:
861:
759:
671:
626:
577:
565:
287:
155:
123:
524:
enantiomers. A single
Adderall dose combines the neutral sulfate salts of
993:
592:
544:
521:
513:
497:
468:
1119:
818:(Recommendations 1996), 2-Carb-4. – Configurational symbols and prefixes
423:. Various methods exist for this separation, including crystallization,
1232:
588:
561:
529:
509:
505:
403:
360:
282:), meaning that such materials do not rotate the polarization of plane-
107:
1421:
540:
501:
20:
1654:
777:"Basic terminology of stereochemistry (IUPAC Recommendations 1996)"
679:
which describes how stereochemistry is denoted in skeletal formulae
548:
533:
517:
440:
407:
16:
Mixture with equal amounts of left- and right-handed chiral isomers
1375:
761:
Basic terminology of stereochemistry (IUPAC Recommendations 1996)
630:
602:
552:
444:
307:
279:
131:
452:
evolved on what is presumed to be a racemic primordial earth.
322:
There are four ways to crystallize a racemate; three of which
49:
1061:"Thalidomide Approved to Treat Leprosy, With Other Uses Seen"
263:
406:
in water. Re-investigated in 2008, the crystals formed are
91:
67:
55:
40:
1159:
982:
American
Journal of Respiratory and Critical Care Medicine
85:
79:
909:
244:
If the ratio is not 1:1 (or is not known), the prefix
842:
Jacques, Jean; Collet, André; Wilen, Samuel H (1981).
359:
If molecules have a greater affinity for the opposite
394:
Pasteur in 1853, forms from a 1:2 mixture of the bis
82:
46:
1104:
1014:
877:
94:
76:
64:
58:
37:
88:
73:
52:
43:
944:
841:
601:is available by prescription under the brand name
1291:Ultraviolet–visible spectroscopy of stereoisomers
1791:
979:
572:and the resulting enantiopure drug is called a
130:found to be a mixture of the two enantiomeric
1391:
1145:
473:
874:
198:A racemic mixture is denoted by the prefix
1398:
1384:
1152:
1138:
580:is a chiral switch of (±)-omeprazole and
481:
792:
1108:Journal of the American Chemical Society
1058:
463:", for their indecision in a particular
1702:Pseudoasymmetric (pseudochiral) centers
1682:CIP (Cahn–Ingold–Prelog) priority rules
1077:
1052:
912:Angewandte Chemie International Edition
844:Enantiomers, racemates, and resolutions
725:Brakel, Jaap van (2012). "Substances".
262:The usage of d and l is discouraged by
1792:
724:
633:crystals tend to be denser than their
584:is a chiral switch of (±)-cetirizine.
1379:
1133:
1059:Stolberg, Sheryl Gay (17 July 1998).
605:. The active component of Desoxyn is
774:
757:
122:The first known racemic mixture was
1405:
607:dextromethamphetamine hydrochloride
547:), the enantiomers interconvert or
427:, and the use of various reagents.
13:
1080:Justus Liebig's Annalen der Chemie
735:10.1016/B978-0-444-51675-6.50018-9
625:Wallach's rule (first proposed by
317:
14:
1826:
1286:NMR spectroscopy of stereoisomers
667:Racemic (protein) crystallography
620:
402:and the bis ammonium salt of (−)-
1324:Diastereomeric recrystallization
677:Skeletal formula#Stereochemistry
439:influence (for example a chiral
259:(with a slash) is used instead.
33:
1098:
1071:
1008:
973:
938:
193:
903:
868:
835:
821:
809:
775:Moss, G. P. (1 January 1996).
768:
751:
718:
703:Merriam-Webster.com Dictionary
690:
520:is an unequal mixture of both
290:) and positive (+) clockwise (
1:
1030:10.1080/14740338.2021.1953467
1018:Expert Opinion on Drug Safety
816:Nomenclature of Carbohydrates
683:
414:
269:
1319:Chiral column chromatography
959:10.1016/j.drudis.2010.01.007
430:
352:Racemic compound (sometimes
158:found in grapes; from Latin
149:
7:
640:
342:mixture. Consequently, the
326:had distinguished by 1899:
10:
1831:
1764:Octahedral propeller twist
1500:Arene substitution pattern
1281:Chiral derivatizing agents
1162:enantioselective synthesis
781:Pure and Applied Chemistry
485:
377:Pseudoracemate (sometimes
117:
106:of left- and right-handed
1778:
1762:
1739:
1720:
1700:
1680:
1671:
1653:
1641:
1618:
1595:
1576:
1558:
1533:
1498:
1471:
1445:
1438:Configuration descriptors
1436:
1413:
1332:
1299:
1268:
1220:
1168:
889:10.1107/S0108768109053610
1781:Category:Stereochemistry
1207:Supramolecular chirality
1092:10.1002/jlac.18952860105
330:Conglomerate (sometimes
102:) is one that has equal
1673:Absolute configurations
1578:Three identical ligands
794:10.1351/pac199668122193
758:Moss, Gerry P. (1996).
727:Philosophy of Chemistry
482:Racemic pharmaceuticals
385:slightly or not at all.
366:kryptoracemic compounds
206:(for sugars the prefix
1741:Relative configuration
924:10.1002/anie.200704007
662:Descriptor (chemistry)
478:
379:racemic solid solution
1810:Chemical nomenclature
1560:Syn and anti addition
1345:Chiral pool synthesis
1259:Diastereomeric excess
539:In some cases (e.g.,
477:
186:as the Swedish name,
140:enantiomerically pure
1590:(facies, meridonal)
1355:Asymmetric catalysis
1340:Asymmetric induction
994:10.1164/rccm.2606001
947:Drug Discovery Today
729:. pp. 191–229.
536:is also a racemate.
332:racemic conglomerate
182:the scientific name
1597:In carbon skeletons
1253:Enantiomeric excess
1120:10.1021/ja00026a015
831:. 15 November 2021.
611:levomethamphetamine
302:are also possible.
241:letters) are used.
1350:Chiral auxiliaries
1314:Kinetic resolution
1212:Inherent chirality
1197:-symmetric ligands
1065:The New York Times
829:"Racemic Mixtures"
560:reagent); compare
479:
324:H. W. B. Roozeboom
276:optically inactive
1815:Organic chemistry
1787:
1786:
1774:
1773:
1667:
1666:
1373:
1372:
1309:Recrystallization
1301:Chiral resolution
1114:(26): 9811–9820.
853:978-0-471-08058-9
787:(12): 2193–2222.
744:978-0-444-51675-6
706:. Merriam-Webster
656:optical isomerism
526:dextroamphetamine
421:chiral resolution
225:) or the symbols
184:Sambucus racemosa
1822:
1805:Racemic mixtures
1756:
1755:
1750:
1749:
1722:Optical rotation
1678:
1677:
1443:
1442:
1400:
1393:
1386:
1377:
1376:
1276:Optical rotation
1221:Chiral molecules
1186:Planar chirality
1154:
1147:
1140:
1131:
1130:
1124:
1123:
1102:
1096:
1095:
1075:
1069:
1068:
1056:
1050:
1049:
1012:
1006:
1005:
977:
971:
970:
953:(5–6): 163–170.
942:
936:
935:
907:
901:
900:
872:
866:
865:
839:
833:
832:
825:
819:
813:
807:
806:
796:
772:
766:
765:
755:
749:
748:
722:
716:
715:
713:
711:
694:
570:chiral switching
488:Enantiopure drug
252:
210:
101:
100:
97:
96:
93:
90:
87:
84:
81:
78:
75:
70:
69:
66:
61:
60:
57:
54:
51:
48:
45:
42:
39:
1830:
1829:
1825:
1824:
1823:
1821:
1820:
1819:
1800:Stereochemistry
1790:
1789:
1788:
1783:
1770:
1758:
1753:
1752:
1747:
1746:
1735:
1716:
1696:
1663:
1649:
1637:
1614:
1591:
1572:
1554:
1529:
1494:
1467:
1432:
1431:
1427:Racemic mixture
1409:
1407:Stereochemistry
1404:
1374:
1369:
1360:Organocatalysis
1328:
1295:
1264:
1248:Racemic mixture
1216:
1202:Axial chirality
1196:
1169:Chirality types
1164:
1158:
1128:
1127:
1103:
1099:
1076:
1072:
1057:
1053:
1013:
1009:
978:
974:
943:
939:
908:
904:
873:
869:
854:
840:
836:
827:
826:
822:
814:
810:
773:
769:
756:
752:
745:
723:
719:
709:
707:
696:
695:
691:
686:
643:
623:
599:Methamphetamine
576:. As examples,
490:
484:
465:stereoisomerism
461:stereoselective
433:
417:
370:kryptoracemates
320:
318:Crystallization
312:methamphetamine
294:) enantiomers.
272:
250:
208:
196:
152:
120:
72:
63:
36:
32:
25:racemic mixture
17:
12:
11:
5:
1828:
1818:
1817:
1812:
1807:
1802:
1785:
1784:
1779:
1776:
1775:
1772:
1771:
1768:
1766:
1760:
1759:
1745:
1743:
1737:
1736:
1727:(+)-, (−)- or
1726:
1724:
1718:
1717:
1706:
1704:
1698:
1697:
1686:
1684:
1675:
1669:
1668:
1665:
1664:
1659:
1657:
1651:
1650:
1647:
1645:
1643:Spiro compound
1639:
1638:
1628:
1626:
1616:
1615:
1601:
1599:
1593:
1592:
1582:
1580:
1574:
1573:
1564:
1562:
1556:
1555:
1546:
1544:
1531:
1530:
1504:
1502:
1496:
1495:
1484:
1482:
1469:
1468:
1458:
1456:
1440:
1434:
1433:
1430:
1429:
1424:
1418:
1417:
1415:
1411:
1410:
1403:
1402:
1395:
1388:
1380:
1371:
1370:
1368:
1367:
1362:
1357:
1352:
1347:
1342:
1336:
1334:
1330:
1329:
1327:
1326:
1321:
1316:
1311:
1305:
1303:
1297:
1296:
1294:
1293:
1288:
1283:
1278:
1272:
1270:
1266:
1265:
1263:
1262:
1256:
1250:
1245:
1240:
1235:
1230:
1224:
1222:
1218:
1217:
1215:
1214:
1209:
1204:
1199:
1194:
1188:
1183:
1178:
1172:
1170:
1166:
1165:
1157:
1156:
1149:
1142:
1134:
1126:
1125:
1097:
1070:
1051:
1007:
988:(9): 965–969.
972:
937:
902:
867:
852:
834:
820:
808:
767:
750:
743:
717:
688:
687:
685:
682:
681:
680:
674:
669:
664:
659:
649:
642:
639:
629:) states that
622:
621:Wallach's rule
619:
582:levocetirizine
558:stereospecific
494:drug molecules
483:
480:
457:stereospecific
432:
429:
425:chromatography
416:
413:
412:
411:
391:
387:
386:
382:
374:
373:
357:
349:
348:
347:conglomerates.
335:
319:
316:
300:boiling points
292:dextrorotatory
274:A racemate is
271:
268:
195:
192:
180:red elderberry
176:Carl von Linné
151:
148:
119:
116:
15:
9:
6:
4:
3:
2:
1827:
1816:
1813:
1811:
1808:
1806:
1803:
1801:
1798:
1797:
1795:
1782:
1777:
1767:
1765:
1761:
1744:
1742:
1738:
1734:
1730:
1725:
1723:
1719:
1714:
1710:
1705:
1703:
1699:
1694:
1690:
1685:
1683:
1679:
1676:
1674:
1670:
1662:
1658:
1656:
1652:
1646:
1644:
1640:
1635:
1631:
1627:
1625:
1621:
1617:
1612:
1608:
1604:
1600:
1598:
1594:
1589:
1585:
1581:
1579:
1575:
1571:
1567:
1563:
1561:
1557:
1553:
1549:
1545:
1543:
1541:
1537:
1532:
1527:
1523:
1519:
1515:
1511:
1507:
1503:
1501:
1497:
1492:
1488:
1483:
1481:
1479:
1475:
1470:
1465:
1461:
1457:
1455:
1453:
1449:
1444:
1441:
1439:
1435:
1428:
1425:
1423:
1420:
1419:
1416:
1412:
1408:
1401:
1396:
1394:
1389:
1387:
1382:
1381:
1378:
1366:
1363:
1361:
1358:
1356:
1353:
1351:
1348:
1346:
1343:
1341:
1338:
1337:
1335:
1331:
1325:
1322:
1320:
1317:
1315:
1312:
1310:
1307:
1306:
1304:
1302:
1298:
1292:
1289:
1287:
1284:
1282:
1279:
1277:
1274:
1273:
1271:
1267:
1260:
1257:
1254:
1251:
1249:
1246:
1244:
1243:Meso compound
1241:
1239:
1236:
1234:
1231:
1229:
1226:
1225:
1223:
1219:
1213:
1210:
1208:
1205:
1203:
1200:
1198:
1193:
1189:
1187:
1184:
1182:
1179:
1177:
1174:
1173:
1171:
1167:
1163:
1155:
1150:
1148:
1143:
1141:
1136:
1135:
1132:
1121:
1117:
1113:
1109:
1101:
1093:
1089:
1086:(1): 90–118.
1085:
1082:(in German).
1081:
1074:
1066:
1062:
1055:
1047:
1043:
1039:
1035:
1031:
1027:
1023:
1019:
1011:
1003:
999:
995:
991:
987:
983:
976:
968:
964:
960:
956:
952:
948:
941:
933:
929:
925:
921:
917:
913:
906:
898:
894:
890:
886:
883:(1): 94–103.
882:
878:
871:
863:
859:
855:
849:
845:
838:
830:
824:
817:
812:
804:
800:
795:
790:
786:
782:
778:
771:
763:
762:
754:
746:
740:
736:
732:
728:
721:
705:
704:
699:
693:
689:
678:
675:
673:
670:
668:
665:
663:
660:
657:
653:
650:
648:
647:Chiral switch
645:
644:
638:
636:
632:
628:
618:
616:
612:
608:
604:
600:
596:
594:
590:
585:
583:
579:
575:
574:chiral switch
571:
567:
563:
559:
555:
554:
550:
546:
542:
537:
535:
531:
527:
523:
519:
515:
511:
507:
503:
499:
495:
489:
476:
472:
470:
466:
462:
458:
453:
451:
450:homochirality
446:
442:
438:
428:
426:
422:
409:
405:
401:
400:tartaric acid
397:
396:ammonium salt
392:
390:Quasiracemate
389:
388:
383:
380:
376:
375:
371:
367:
362:
358:
355:
354:true racemate
351:
350:
345:
344:melting point
341:
336:
333:
329:
328:
327:
325:
315:
313:
309:
303:
301:
295:
293:
289:
285:
281:
277:
267:
265:
260:
258:
254:
247:
242:
240:
236:
235:
230:
229:
224:
223:
218:
217:
212:
205:
201:
191:
189:
185:
181:
177:
173:
169:
165:
164:tartaric acid
161:
157:
147:
145:
141:
137:
136:tartaric acid
133:
129:
128:Louis Pasteur
125:
115:
113:
109:
105:
99:
30:
26:
22:
1732:
1728:
1712:
1708:
1692:
1688:
1660:
1633:
1629:
1610:
1606:
1602:
1587:
1583:
1569:
1565:
1551:
1547:
1539:
1535:
1525:
1521:
1517:
1513:
1509:
1505:
1490:
1486:
1477:
1473:
1463:
1459:
1451:
1447:
1426:
1365:Biocatalysis
1247:
1238:Diastereomer
1228:Stereoisomer
1191:
1181:Stereocenter
1160:Concepts in
1111:
1107:
1100:
1083:
1079:
1073:
1064:
1054:
1024:(1): 67–81.
1021:
1017:
1010:
985:
981:
975:
950:
946:
940:
918:(1): 78–81.
915:
911:
905:
880:
876:
870:
843:
837:
823:
811:
784:
780:
770:
760:
753:
726:
720:
708:. Retrieved
701:
692:
672:Racemization
627:Otto Wallach
624:
597:
586:
578:esomeprazole
569:
566:esomeprazole
551:
538:
491:
454:
434:
418:
378:
353:
331:
321:
304:
296:
288:levorotatory
273:
261:
256:
249:
245:
243:
238:
233:
232:
227:
226:
221:
220:
215:
214:
207:
203:
199:
197:
194:Nomenclature
187:
183:
171:
170:and Swedish
168:traubensäure
167:
159:
156:racemic acid
153:
143:
139:
124:racemic acid
121:
28:
24:
18:
593:thalidomide
545:thalidomide
522:amphetamine
514:amphetamine
498:thalidomide
469:carbocation
144:enantiopure
108:enantiomers
1794:Categories
1233:Enantiomer
698:"racemate"
684:References
589:salbutamol
562:omeprazole
530:Benzedrine
510:salbutamol
506:cetirizine
486:See also:
459:" or "not
435:Without a
415:Resolution
404:malic acid
361:enantiomer
270:Properties
188:druvfläder
146:compound.
1620:Secondary
1542:isomerism
1454:isomerism
1422:Chirality
1333:Reactions
1176:Chirality
1046:235759079
846:. Wiley.
654:(same as
652:Chirality
541:ibuprofen
502:ibuprofen
431:Synthesis
284:polarized
150:Etymology
21:chemistry
1655:Catenane
1624:tertiary
1480:notation
1269:Analysis
1038:34232089
1002:17060667
967:20116449
932:18022885
897:20101089
803:98272391
641:See also
613:, is an
549:racemize
534:tramadol
518:Adderall
441:catalyst
408:dumbbell
340:eutectic
237:(all in
172:druvsyra
126:, which
29:racemate
1613:, cyclo
1476:–
862:7174200
631:racemic
603:Desoxyn
553:in vivo
445:solvent
398:of (+)-
308:glucose
280:achiral
246:(+)/(−)
160:racemus
132:isomers
118:History
104:amounts
1769:Λ-, Δ-
1661:catena
1414:Topics
1044:
1036:
1000:
965:
930:
895:
860:
850:
801:
741:
710:8 July
635:chiral
437:chiral
239:italic
222:racem-
112:chiral
1648:spiro
1518:ortho
1489:)-, (
1464:trans
1452:trans
1042:S2CID
799:S2CID
492:Some
264:IUPAC
178:gave
154:From
110:of a
1711:), (
1691:), (
1634:tert
1622:and
1570:anti
1548:endo
1536:Endo
1526:para
1522:meta
1261:(de)
1255:(ee)
1034:PMID
998:PMID
963:PMID
928:PMID
893:PMID
858:OCLC
848:ISBN
739:ISBN
712:2018
591:and
564:and
543:and
508:and
368:(or
310:and
257:d/l-
231:and
219:(or
216:rac-
200:(±)-
23:, a
1751:-,
1632:-,
1630:sec
1611:neo
1607:iso
1588:mer
1584:fac
1566:syn
1552:exo
1550:,
1540:exo
1516:- (
1512:-,
1508:-,
1462:-,
1460:cis
1448:cis
1116:doi
1112:113
1088:doi
1084:286
1026:doi
990:doi
986:174
955:doi
920:doi
885:doi
789:doi
731:doi
615:OTC
255:or
251:d/l
204:dl-
202:or
142:or
134:of
27:or
19:In
1796::
1733:l-
1731:,
1729:d-
1609:,
1605:,
1586:,
1568:,
1524:,
1520:,
1493:)-
1110:.
1063:.
1040:.
1032:.
1022:21
1020:.
996:.
984:.
961:.
951:15
949:.
926:.
916:47
914:.
891:.
881:66
879:.
856:.
797:.
785:68
783:.
779:.
737:.
700:.
516:.
504:,
500:,
443:,
314:.
266:.
248:,
234:SR
228:RS
209:dl
174:.
92:eɪ
71:-,
56:eɪ
50:iː
41:eɪ
1757:-
1754:L
1748:D
1715:)
1713:s
1709:r
1707:(
1695:)
1693:S
1689:R
1687:(
1636:-
1603:n
1538:-
1528:)
1514:p
1510:m
1506:o
1491:Z
1487:E
1485:(
1478:Z
1474:E
1466:-
1450:–
1399:e
1392:t
1385:v
1195:2
1192:C
1153:e
1146:t
1139:v
1122:.
1118::
1094:.
1090::
1067:.
1048:.
1028::
1004:.
992::
969:.
957::
934:.
922::
899:.
887::
864:.
805:.
791::
747:.
733::
714:.
658:)
381:)
356:)
334:)
278:(
253:-
211:-
98:/
95:t
89:m
86:ɪ
83:s
80:æ
77:r
74:ˈ
68:ə
65:r
62:,
59:t
53:m
47:s
44:ˈ
38:r
35:/
31:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.