361:
613:
757:
521:
107:
164:
559:
195:
45:, the intramolecular esterification of the corresponding hydroxycarboxylic acids, which takes place spontaneously when the ring that is formed is five- or six-membered. Lactones with three- or four-membered rings (α-lactones and β-lactones) are very reactive, making their isolation difficult. Special methods are normally required for the laboratory synthesis of small-ring lactones as well as those that contain rings larger than six-membered.
141:
230:
1176:(It's desirable for this group of compounds — whose simplest representative until now has been the substance that's described in the preceding — to have a general designation, and since the name "lactide" isn't applicable because then the archetypal lactide would not be a lactide, we therefore suggest the name "lactone" as the designation of this group .)
1174:"Es ist wünschenswerth, für diese Gruppe von Verbindungen, deren bis jetzt einfachster Repräsentant der im Vorstehenden beschriebene Körper ist, eine allgemeine Bezeichnungsweise zu haben, und da der Name "Lactide" nicht anwendbar ist, weil dann das Lactid κατ εξοχην kein Lactid sein wurde, so schlagen wir als Gruppenbezeichnung den Namen "Lactone" vor".
262:
suffix and a Greek letter prefix that specifies the number of carbon atoms in the heterocycle — that is, the distance between the relevant -OH and the -COOH groups along said backbone. The first carbon atom after the carbon in the -COOH group on the parent compound is labelled α, the second will be
703:
of the hydrolysis of lactones is less than the entropy of straight-chained esters. Straight-chained esters give two products upon hydrolysis, making the entropy change more favorable than in the case of lactones which gives only a single product.
1065:"Indépendamment de la lactide dont je viens de rappeler l'existence dans les produits de la distllation de l'acide lactique, celui-ci donne encore, par sa décomposition, une autre substance, que je propose d'appeler
1071:(Independently of the lactide of which I have just recalled the existence in the products of the distillation of lactic acid, this gives further, by its decomposition, another substance, which I propose to call
695:
of the hydrolysis reaction of the lactone is lower than that of the straight-chained ester i.e. the products (hydroxyacids) are less favored in the case of the lactones. This is because although the
263:
labeled β, and so forth. Therefore, the prefixes also indicate the size of the lactone ring: α-lactone = 3-membered ring, β-lactone = 4-membered, γ-lactone = 5-membered, δ-lactone = 6-membered, etc.
309:, lactones are named as heterocyclic pseudoketones by adding the suffix 'one', 'dione', 'thione', etc. and the appropriate multiplicative prefixes to the name of the heterocyclic parent hydride.
820:. Replacement of a methylene unit by oxygen barely affects the odor of these compounds, and oxalactones with 15 – 17-membered rings are produced in addition to cyclopentadecanolide (e. g.,
773:
Lactones contribute significantly to the flavor of fruit, and of unfermented and fermented dairy products, and are therefore used as flavors and fragrances. Some examples are
378:
5-Membered γ-lactones and 6-membered δ-lactones are prevalent. β-lactones appear in a number of natural products. α‑Lactones can be detected as transient species in
333:-CH(OH)-COOH. Lactic acid, in turn, derives its name from its original isolation from soured milk (Latin: lac, lactis). The name was coined in 1844 by the French chemist
801:
874:
821:
683:
the lactone to its parent compound, the straight chained bifunctional compound. Like straight-chained esters, the hydrolysis-condensation reaction of lactones is a
781:(5-decanolide), which has a creamy coconut/peach flavour; γ-dodecalactone (4-dodecanolide), which also has a coconut/fruity flavor, a description which also fits
893:
633:
1377:
1246:
965:
449:
532:
for longer hydroxy acids, or the strained β‑lactones. γ‑Lactones, on the other hand, are so stable that 4-hydroxy acids (R-CH(OH)-(CH
205:
174:
119:
92:
1482:
Odile Dechy-Cabaret; Blanca Martin-Vaca; Didier
Bourissou (2004). "Controlled Ring-Opening Polymerization of Lactide and Glycolide".
1186:
Danheiser, Rick L.; Nowick, James S. (1991) . "A practical and efficient method for the synthesis of β‑lactones".
1466:
1033:
999:
656:
1081:
960:
1603:
1569:
1535:
1151:
1132:
598:
1220:. International Journal of Mass Spectrometry and Ion Processes, Volumes 165-166, November issue, Pages 71-82.
602:
854:
751:(polylactide). The resulting polylactic acid has been heavily investigated for commercial applications.
1696:
1628:"Polyesters as a Model System for Building Primitive Biologies from Non-Biological Prebiotic Chemistry"
1017:
334:
716:
594:
528:
Many methods in ester synthesis can also be applied to that of lactones. Lactonization competes with
1050:
1014:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
606:
590:
884:
1392:
Chandru, Kuhan; Jia, Tony Z.; Mamajanov, Irena; Bapat, Niraja; Cleaves, H. James (2020-10-16).
649:
579:
349:
27:
1593:
1525:
1118:
1559:
1394:"Prebiotic oligomerization and self-assembly of structurally diverse xenobiological monomers"
1100:
995:
364:
789:, which has an intense coconut flavor of this series, despite not occurring in coconut, and
1639:
1405:
1311:
1069:, parce qu'elle me paraît être à l'acide lactique ce que l'acétone est à l'acide acétique."
859:
797:
692:
688:
386:
338:
306:
8:
1339:
684:
342:
1643:
1409:
1662:
1627:
1434:
1393:
1343:
53:
1225:
835:
is an important plastic. Its formation has even been considered in the context of the
185:
1691:
1667:
1599:
1565:
1531:
1499:
1481:
1462:
1439:
1421:
1355:
1331:
1323:
1128:
1029:
933:
567:
509:
379:
1262:
360:
1657:
1647:
1491:
1429:
1413:
1327:
1315:
1287:
1221:
1195:
1163:
1021:
832:
813:
676:
637:
552:
489:
461:
418:
23:
1626:
Chandru, Kuhan; Mamajanov, Irena; Cleaves, H. James; Jia, Tony Z. (January 2020).
1459:
Poly(lactic acid): Synthesis, Structures, Properties, Processing, and
Applications
786:
782:
778:
774:
629:
625:
621:
1218:
Generation of α-acetolactone and the acetoxyl diradical •CH2COO• in the gas phase
748:
583:
505:
410:
70:
1025:
1417:
1363:
1213:
1075:, because it seems to me to be to lactic acid what acetone is to acetic acid.)
641:
529:
485:
445:
437:
31:
1685:
1425:
1167:
501:
465:
433:
425:
390:
298:
756:
612:
1671:
1503:
1443:
848:
743:
Some lactones convert to polyesters: For example the double lactone called
707:
Lactones also react with amines to give the ring-opened alcohol and amide.
645:
481:
106:
100:
1282:
John E. Cabaj, David Kairys, and Thomas R. Benson Org. Process Res. Dev.;
790:
151:
1652:
1558:
Mehta, Bhavbhuti M.; Kamal-Eldin, Afaf; Iwanski, Robert Z., eds. (2012).
1303:
836:
548:
520:
497:
326:
292:
264:
163:
1199:
582:
with the cationic intermediate captured intramolecularly by an adjacent
1456:
1307:
493:
473:
469:
394:
280:
76:
35:
1495:
1374:
1291:
194:
938:
817:
680:
477:
457:
352:
extended the name "lactone" to all intramolecular carboxylic esters.
286:
238:
Lactones are usually named according to the precursor acid molecule (
1375:
1244:
Karl-Georg
Fahlbusch; et al. (2007), "Flavors and Fragrances",
558:
424:
Lactone rings occur widely as building blocks in nature, such as in
337:, who first obtained it as a derivative of lactic acid. An internal
1527:
Flavours and fragrances chemistry, bioprocessing and sustainability
1335:
809:
696:
441:
406:
371:
325:, which is formed from the dehydration of 2-hydroxypropanoic acid (
978:
924:
869:
805:
744:
719:. For instance, gamma-lactones is reduced to butane-1,4-diol, (CH
700:
699:
of the hydrolysis of esters and lactones are about the same, the
575:
453:
322:
1154:[Investigations into unsaturated acids, third article].
1125:
Dictionary of
Chemistry: an etymological and historical approach
140:
1120:
Dictionnaire de chimie: Une approche étymologique et historique
915:
906:
571:
429:
402:
398:
229:
804:) have odors similar to macrocyclic ketones of animal origin (
1319:
1127:] (in French). Brussels, Belgium: de boeck. p. 183.
928:
919:
910:
785:(4-octanolide), although it also has a herbaceous character;
341:
within the same molecule of lactic acid would have produced
1152:"Untersuchungen über ungesättige Säuren, dritte Abhandlung"
655:
An alternative radical reaction yielding γ-lactones is the
1625:
1280:
Development of a
Commercial Process to Produce Oxandrolone
385:
Macrocyclic lactones are also important natural products.
1598:. Boca Raton, FL: CRC/Taylor & Francis. p. 242.
1263:"The Oxford Companion to Beer definition of barrel-aging"
812:), but they can be prepared more easily, for example, by
777:(4-decanolide), which has a characteristic peach flavor;
667:
Lactones exhibit the reactions characteristic of esters.
414:
1391:
616:γ-Lactone synthesis from fatty alcohols and acrylic acid
1557:
636:
can be prepared in good yield in a one-step process by
1457:
R. Auras; L.-T. Lim; S. E. M. Selke; H. Tsuji (2010).
34:. They can be saturated or unsaturated. Some contain
1243:
1212:
Detlef Schröder, Norman
Goldberg, Waltraud Zummack,
417:
wood, and they contribute to the flavour profile of
393:oil. Of the naturally occurring bicyclic lactones,
966:International Union of Pure and Applied Chemistry
1683:
1564:. Boca Raton: Taylor & Francis. p. 74.
1216:, John C. Poutsma and Robert R. Squires (1997),
38:replacing one or more carbon atoms of the ring.
1334:with ring-opening and finally reduction of the
1185:
993:
1378:Ullmann's Encyclopedia of Industrial Chemistry
1358:, Coll. Vol. 7, p.164 (1990); Vol. 64, p.175 (
1247:Ullmann's Encyclopedia of Industrial Chemistry
998:. Department of Chemistry & Biochemistry,
983:(8th ed.), McGraw-Hill, pp. 798–799
979:Francis A. Carey; Robert M. Giuliano (2011),
274:The other suffix used to denote a lactone is
670:
105:
1519:
1517:
1515:
1513:
1179:
996:"Illustrated Glossary of Organic Chemistry"
56:in alphabetical order indicate ring size.
26:. They are derived from the corresponding
1661:
1651:
1433:
768:
1510:
611:
557:
519:
389:is responsible for the musklike odor of
359:
1591:
1561:Fermentation effects on food properties
1098:
1079:
1048:
944:
715:Lactones can be reduced to diols using
1684:
1523:
1149:
1116:
896:(Musk T), a widely used synthetic musk
887:can be isolated from the heartwood of
321:derives from the ring compound called
1250:(7th ed.), Wiley, pp. 74‒78
1239:
1237:
1235:
1233:
278:, used in substance class names like
1346:and intramolecular lactone formation
851:(Hexahydroxydiphenic acid dilactone)
345:, a lactone with a 3-membered ring.
551:the key lactone-forming step is an
13:
1302:The complete reaction sequence is
1260:
1230:
961:Compendium of Chemical Terminology
14:
1708:
1084:[Memoir on lactic acid].
1053:[Memoir on lactic acid].
738:
599:Corey-Nicolaou macrolactonization
397:are responsible for the odors of
1595:Sensory-directed flavor analysis
1156:Annalen der Chemie und Pharmacie
1099:Pelouze, J. (January 15, 1845).
1086:Annales de Chimie et de Physique
755:
228:
193:
162:
139:
1619:
1585:
1551:
1475:
1450:
1385:
1368:
1349:
1296:
1273:
1254:
1049:Pelouze, J. (9 December 1844).
675:Heating a lactone with a base (
547:In one industrial synthesis of
48:
1286:; 11(3) pp 378–388; (Article)
1206:
1143:
1082:"Mémoire sur l'acide lactique"
1051:"Mémoire sur l'acide lactique"
1042:
1018:The Royal Society of Chemistry
1006:
987:
972:
951:
1:
1226:10.1016/S0168-1176(97)00150-X
842:
355:
1188:Journal of Organic Chemistry
855:Flavogallonic acid dilactone
816:of the corresponding linear
710:
662:
515:
312:
7:
1101:"Researches on lactic acid"
1026:10.1039/9781849733069-00648
900:
827:
657:manganese-mediated coupling
348:In 1880 the German chemist
10:
1713:
1592:Marsili, Ray, ed. (2007).
1524:Berger, R.G., ed. (2007).
1418:10.1038/s41598-020-74223-5
1117:Menten, Pierre de (2013).
1088:. 3rd series (in French).
544:H) spontaneously cyclize.
413:. Lactones are present in
968:, 2014-02-24, p. 817
802:15-pentadec-11/12-enolide
717:lithium aluminium hydride
671:Hydrolysis and aminolysis
603:Baeyer–Villiger oxidation
595:Shiina macrolactonization
589:Specific methods include
1168:10.1002/jlac.18802000102
1150:Fittig, Rudolph (1880).
875:Tergallic acid dilactone
822:12-oxa-16-hexadecanolide
607:nucleophilic abstraction
591:Yamaguchi esterification
885:Valoneic acid dilactone
763:
335:Théophile-Jules Pelouze
41:Lactones are formed by
28:hydroxycarboxylic acids
16:Cyclic carboxylic ester
1267:Craft Beer and Brewing
1097:English translation:
796:Macrocyclic lactones (
769:Flavors and fragrances
650:di-tert-butyl peroxide
617:
580:electrophilic addition
563:
525:
375:
350:Wilhelm Rudolph Fittig
267:lactones are known as
110:
1381:(7th ed.), Wiley
1020:. 2014. p. 822.
994:Steven A. Hardinger.
615:
561:
524:Oxandrolone synthesis
523:
363:
307:preferred IUPAC names
109:
1653:10.3390/life10010006
1530:. Berlin: Springer.
1312:elimination reaction
1105:The Chemical Gazette
1080:Pelouze, J. (1845).
945:References and notes
879:Rhynchosia volubilis
860:Rhynchosia volubilis
798:cyclopentadecanolide
693:equilibrium constant
387:Cyclopentadecanolide
339:dehydration reaction
1644:2020Life...10....6C
1410:2020NatSR..1017560C
1200:10.1021/jo00003a047
1094: ; see p. 262.
894:Ethylene brassylate
685:reversible reaction
343:alpha-propiolactone
258:= 6, etc.), with a
84:Structure, comment
1398:Scientific Reports
1344:sodium borohydride
1113: ; see p. 31.
618:
564:
555:– esterification.
526:
510:cardiac glycosides
376:
368:-glucono-δ-lactone
242:= 2 carbon atoms,
111:
1697:Functional groups
1496:10.1021/cr040002s
1468:978-0-470-29366-9
1356:Organic Syntheses
1332:lead tetraacetate
1324:organic oxidation
1310:(not displayed),
1292:10.1021/op060231b
1261:Oliver, Garrett.
1035:978-0-85404-182-4
981:Organic Chemistry
934:Halolactonization
889:Shorea laeviforia
865:Shorea laeviforia
574:is attacked by a
568:halolactonization
562:iodolactonization
462:neurotransmitters
419:barrel-aged beers
380:mass spectrometry
367:
236:
235:
24:carboxylic esters
1704:
1676:
1675:
1665:
1655:
1623:
1617:
1616:
1614:
1612:
1589:
1583:
1582:
1580:
1578:
1555:
1549:
1548:
1546:
1544:
1521:
1508:
1507:
1479:
1473:
1472:
1454:
1448:
1447:
1437:
1389:
1383:
1382:
1372:
1366:
1353:
1347:
1328:osmium tetroxide
1316:lithium chloride
1300:
1294:
1277:
1271:
1270:
1258:
1252:
1251:
1241:
1228:
1210:
1204:
1203:
1194:(3): 1176–1185.
1183:
1177:
1171:
1147:
1141:
1138:
1112:
1093:
1062:
1046:
1040:
1039:
1010:
1004:
1003:
991:
985:
984:
976:
970:
969:
955:
877:can be found in
857:can be found in
833:Polycaprolactone
814:depolymerization
759:
677:sodium hydroxide
638:radical addition
553:organic reaction
490:anticancer drugs
365:
232:
197:
166:
159:γ-Butyrolactone
143:
73:
64:(number of atoms
59:
58:
1712:
1711:
1707:
1706:
1705:
1703:
1702:
1701:
1682:
1681:
1680:
1679:
1624:
1620:
1610:
1608:
1606:
1590:
1586:
1576:
1574:
1572:
1556:
1552:
1542:
1540:
1538:
1522:
1511:
1490:(12): 6147–76.
1480:
1476:
1469:
1455:
1451:
1390:
1386:
1373:
1369:
1354:
1350:
1301:
1297:
1278:
1274:
1259:
1255:
1242:
1231:
1211:
1207:
1184:
1180:
1148:
1144:
1135:
1063:From p. 1223:
1047:
1043:
1036:
1012:
1011:
1007:
992:
988:
977:
973:
957:
956:
952:
947:
903:
845:
830:
791:γ-undecalactone
771:
766:
749:polylactic acid
747:polymerizes to
741:
734:
730:
726:
722:
713:
691:. However, the
673:
665:
652:as a catalyst.
634:γ-undecalactone
620:The γ-lactones
584:carboxylic acid
543:
539:
535:
518:
506:resorcylic acid
450:mevalonolactone
358:
332:
315:
225:
190:
186:δ-Valerolactone
136:
130:β-Propiolactone
81:Parent lactone
71:Systematic name
69:
65:
63:
51:
17:
12:
11:
5:
1710:
1700:
1699:
1694:
1678:
1677:
1618:
1604:
1584:
1570:
1550:
1536:
1509:
1474:
1467:
1449:
1384:
1367:
1348:
1295:
1272:
1253:
1229:
1214:Helmut Schwarz
1205:
1178:
1142:
1140:
1139:
1133:
1114:
1095:
1055:Comptes rendus
1041:
1034:
1005:
986:
971:
949:
948:
946:
943:
942:
941:
936:
931:
922:
913:
902:
899:
898:
897:
891:
882:
872:
867:
852:
844:
841:
837:origin of life
829:
826:
770:
767:
765:
762:
761:
760:
740:
739:Polymerization
737:
732:
728:
724:
720:
712:
709:
672:
669:
664:
661:
642:fatty alcohols
541:
537:
533:
530:polymerization
517:
514:
502:phytoestrogens
486:amphotericin B
446:spironolactone
438:gluconolactone
382:experiments.
357:
354:
330:
314:
311:
305:To obtain the
234:
233:
226:
224:
223:
220:
217:
216:ε-Caprolactone
213:
211:
208:
203:
199:
198:
191:
189:
188:
182:
180:
177:
172:
168:
167:
160:
157:
154:
149:
145:
144:
137:
135:
134:
131:
127:
125:
122:
117:
113:
112:
103:
98:
95:
90:
86:
85:
82:
79:
74:
67:
54:Greek prefixes
50:
47:
32:esterification
15:
9:
6:
4:
3:
2:
1709:
1698:
1695:
1693:
1690:
1689:
1687:
1673:
1669:
1664:
1659:
1654:
1649:
1645:
1641:
1637:
1633:
1629:
1622:
1607:
1605:9781420017045
1601:
1597:
1596:
1588:
1573:
1571:9781439853351
1567:
1563:
1562:
1554:
1539:
1537:9783540493396
1533:
1529:
1528:
1520:
1518:
1516:
1514:
1505:
1501:
1497:
1493:
1489:
1485:
1478:
1470:
1464:
1460:
1453:
1445:
1441:
1436:
1431:
1427:
1423:
1419:
1415:
1411:
1407:
1403:
1399:
1395:
1388:
1380:
1379:
1371:
1365:
1361:
1357:
1352:
1345:
1341:
1337:
1333:
1329:
1325:
1321:
1317:
1313:
1309:
1305:
1299:
1293:
1289:
1285:
1281:
1276:
1268:
1264:
1257:
1249:
1248:
1240:
1238:
1236:
1234:
1227:
1223:
1219:
1215:
1209:
1201:
1197:
1193:
1189:
1182:
1175:
1172:From p. 62:
1169:
1165:
1161:
1158:(in German).
1157:
1153:
1146:
1136:
1134:9782804181758
1130:
1126:
1122:
1121:
1115:
1110:
1106:
1102:
1096:
1091:
1087:
1083:
1077:
1076:
1074:
1070:
1066:
1060:
1057:(in French).
1056:
1052:
1045:
1037:
1031:
1027:
1023:
1019:
1016:. Cambridge:
1015:
1009:
1001:
997:
990:
982:
975:
967:
963:
962:
954:
950:
940:
937:
935:
932:
930:
927:, a cyclic di
926:
923:
921:
917:
914:
912:
908:
905:
904:
895:
892:
890:
886:
883:
880:
876:
873:
871:
868:
866:
863:seeds and in
862:
861:
856:
853:
850:
847:
846:
840:
838:
834:
825:
823:
819:
815:
811:
807:
803:
799:
794:
792:
788:
787:γ-nonalactone
784:
783:γ-octalactone
780:
779:δ-decalactone
776:
775:γ-decalactone
758:
754:
753:
752:
750:
746:
736:
718:
708:
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690:
686:
682:
678:
668:
660:
658:
653:
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647:
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639:
635:
631:
630:γ-decalactone
627:
626:γ-nonalactone
623:
622:γ-octalactone
614:
610:
608:
604:
600:
596:
592:
587:
585:
581:
577:
573:
569:
560:
556:
554:
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545:
531:
522:
513:
511:
507:
503:
499:
495:
491:
487:
483:
479:
475:
471:
467:
466:butyrolactone
463:
459:
455:
451:
447:
443:
439:
435:
434:nepetalactone
431:
427:
426:ascorbic acid
422:
420:
416:
412:
408:
404:
400:
396:
392:
391:angelica root
388:
383:
381:
373:
369:
362:
353:
351:
346:
344:
340:
336:
328:
324:
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310:
308:
303:
301:
300:
299:bufadienolide
295:
294:
289:
288:
283:
282:
277:
272:
270:
269:macrolactones
266:
261:
257:
253:
249:
245:
241:
231:
227:
221:
218:
215:
214:
212:
210:Oxepan-2-one
209:
207:
204:
201:
200:
196:
192:
187:
184:
183:
181:
178:
176:
173:
170:
169:
165:
161:
158:
156:Oxolan-2-one
155:
153:
150:
147:
146:
142:
138:
133:Propiolactone
132:
129:
128:
126:
124:Oxetan-2-one
123:
121:
118:
115:
114:
108:
104:
102:
99:
97:Oxiran-2-one
96:
94:
91:
88:
87:
83:
80:
78:
75:
72:
68:
66:in the ring)
61:
60:
57:
55:
46:
44:
43:lactonization
39:
37:
33:
29:
25:
21:
1635:
1631:
1621:
1609:. Retrieved
1594:
1587:
1575:. Retrieved
1560:
1553:
1541:. Retrieved
1526:
1487:
1483:
1477:
1458:
1452:
1404:(1): 17560.
1401:
1397:
1387:
1376:
1370:
1364:Article link
1359:
1351:
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1208:
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1187:
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1173:
1159:
1155:
1145:
1124:
1119:
1111:(54): 29–35.
1108:
1104:
1089:
1085:
1078:Reprinted:
1072:
1068:
1064:
1061:: 1219–1227.
1058:
1054:
1044:
1013:
1008:
989:
980:
974:
959:
958:"lactones",
953:
888:
878:
864:
858:
849:Ellagic acid
831:
795:
772:
742:
714:
706:
674:
666:
654:
646:acrylic acid
619:
588:
565:
546:
527:
482:erythromycin
423:
384:
377:
347:
318:
316:
304:
297:
291:
285:
279:
275:
273:
268:
259:
255:
251:
247:
243:
239:
237:
219:Caprolactone
101:Acetolactone
52:
49:Nomenclature
42:
40:
19:
18:
1304:bromination
918:, a cyclic
909:, a cyclic
689:equilibrium
640:of primary
549:oxandrolone
498:epothilones
474:antibiotics
470:avermectins
327:lactic acid
293:cardenolide
265:Macrocyclic
179:Oxan-2-one
36:heteroatoms
22:are cyclic
1686:Categories
1308:haloketone
1092:: 257–268.
843:Dilactones
818:polyesters
697:enthalpies
687:, with an
508:lactones,
494:vernolepin
478:macrolides
405:oils, and
395:phthalides
356:Occurrence
281:butenolide
222:Hexanolide
77:IUPAC name
1484:Chem. Rev
1461:. Wiley.
1426:2045-2322
964:, 2.3.3,
939:Phthalein
711:Reduction
681:hydrolyse
663:Reactions
516:Synthesis
458:lactonase
317:The name
313:Etymology
287:macrolide
206:ε-lactone
175:δ-lactone
152:γ-lactone
120:β-lactone
93:α-lactone
62:Ring size
1692:Lactones
1672:31963928
1638:(1): 6.
1504:15584698
1444:33067516
1336:aldehyde
1162:: 1–96.
901:See also
828:Plastics
810:civetone
723:(OH)-(CH
648:, using
442:hormones
411:woodruff
407:coumarin
260:-lactone
20:Lactones
1663:7175156
1640:Bibcode
1435:7567815
1406:Bibcode
1340:alcohol
1338:to the
1073:lactone
1067:lactone
925:Lactide
870:Lactide
806:muscone
745:lactide
701:entropy
679:) will
576:halogen
454:enzymes
323:lactide
319:lactone
1670:
1660:
1611:2 July
1602:
1577:2 July
1568:
1543:2 July
1534:
1502:
1465:
1442:
1432:
1424:
1318:to an
1131:
1032:
916:Lactim
907:Lactam
735:(OH).
572:alkene
430:kavain
403:lovage
399:celery
276:-olide
252:valero
248:butyro
244:propio
1342:with
1320:enone
1314:with
1306:to a
1123:[
929:ester
920:imide
911:amide
881:seeds
570:, an
480:like
256:capro
254:= 5,
250:= 4,
246:= 3,
240:aceto
1668:PMID
1632:Life
1613:2015
1600:ISBN
1579:2015
1566:ISBN
1545:2015
1532:ISBN
1500:PMID
1463:ISBN
1440:PMID
1422:ISSN
1360:1986
1330:and
1284:2007
1129:ISBN
1030:ISBN
1000:UCLA
764:Uses
605:and
578:via
409:for
401:and
372:E575
329:) CH
1658:PMC
1648:doi
1492:doi
1488:104
1430:PMC
1414:doi
1326:by
1288:doi
1222:doi
1196:doi
1164:doi
1160:200
1022:doi
824:).
731:-CH
644:to
566:In
540:-CO
512:).
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415:oak
296:or
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