609:
632:
242:
27:
667:
with a water molecule had suggested an activation barrier of 150 kJ/mol for a single molecule in solvent, much too high for the observed rate. Therefore, it was concluded that this reaction, conducted in the solid phase in plant material with a high fraction of carboxylic acids, follows a pseudo
668:
first order kinetics in which a nearby carboxylic acid precipitates without affecting the observed rate constant. Two transition states corresponding to indirect and direct keto-enol routes are possible, with energies of 93 and 104 kJ/mol. Both intermediates involve protonation of the
659:. The log fraction of THCA present decreases steadily over time, and the rate of decrease varies according to temperature. At 10-degree increments from 100 to 140 °C, half of the THCA is consumed in 30, 11, 6, 3, and 2 minutes; hence the rate constant follows
1072:
Perrotin-Brunel, Helene; Buijs, Wim; Spronsen, Jaap van; Roosmalen, Maaike J.E. van; Peters, Cor J.; Verpoorte, Rob; Witkamp, Geert-Jan (2011). "Decarboxylation of Δ9-tetrahydrocannabinol: Kinetics and molecular modeling".
1172:
Hashimoto, Mitsunori; Eda, Yutaka; Osanai, Yasutomo; Iwai, Toshiaki; Aoki, Seiichi (1986). "A Novel
Decarboxylation of α-Amino Acides. A Facile Method of Decarboxylation by the Use of 2-Cyclohexen-1-one as a Catalyst".
1108:
Perrotin-Brunel, Helene; Buijs, Wim; Spronsen, Jaap van; Roosmalen, Maaike J.E. van; Peters, Cor J.; Verpoorte, Rob; Witkamp, Geert-Jan (February 2011).
784:
759:
338:
Decarboxylations are pervasive in biology. They are often classified according to the cofactors that catalyze the transformations.
1050:
387:-dependent decarboxylases are involved in transformations of cysteine. Iron-based hydroxylases operate by reductive activation of
219:
For the free acids, conditions that deprotonate the carboxyl group (possibly protonating the electron-withdrawing group to form a
663:, ranging between 10 and 10 in a linear log-log relationship with inverse temperature. However, modelling of decarboxylation of
635:
Tetrahydrocannabinolic acid. The decarboxylation of this compound by heat is essential for the psychoactive effect of smoked
1147:
672:, disrupting one of the double bonds of the aromatic ring and permitting the beta-keto group (which takes the form of an
1015:
Li, T.; Huo, L.; Pulley, C.; Liu, A. (2012). "Decarboxylation mechanisms in biological system. Bioorganic
Chemistry".
858:
732:
1205:
820:
264:
118:
Decarboxylation is one of the oldest known organic reactions. It is one of the processes assumed to accompany
164:
652:
318:
As described above, most decarboxylations start with a carboxylic acid or its alkali metal salt, but the
201:
148:
57:, removing a carbon atom from a carbon chain. The reverse process, which is the first chemical step in
755:
445:
296:
256:
576:
205:
123:
78:
647:
Upon heating, Δ9-tetrahydrocannabinolic acid decarboxylates to give the psychoactive compound Δ9-
592:
586:
319:
260:
197:
619:
Straight-chain fatty acid synthesis occurs by recurring reactions involving decarboxylation of
312:
887:
722:
144:
1121:
1082:
656:
648:
304:
8:
596:
395:
380:
1125:
1086:
1058:
992:
967:
582:
300:
263:
thus treat aryl carboxylates as an aryl anion synthon; this synthetic strategy is the
1109:
1032:
997:
854:
738:
728:
660:
572:
561:
38:
147:. Typically, carboxylic acids decarboxylate slowly, but carboxylic acids with an α
1182:
1133:
1129:
1094:
1090:
1024:
987:
979:
948:
917:
846:
799:
473:
278:
248:
209:
54:
1057:. Lipid Library, The American Oil Chemists' Society. 30 April 2011. Archived from
756:"Decarboxylation, Dr. Ian A. Hunt, Department of Chemistry, University of Calgary"
702:. However, using such catalysts may also yield an amount of unwanted by-products.
1028:
968:"Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions"
608:
168:
17:
1051:"Fatty Acids: Straight-chain Saturated, Structure, Occurrence and Biosynthesis"
664:
355:
308:
286:
282:
156:
90:
74:
58:
46:
42:
1151:
1199:
1110:"Decarboxylation of Δ9-tetrahydrocannabinol: Kinetics and molecular modeling"
952:
921:
850:
742:
724:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition
695:
688:
631:
505:
469:
271:
98:
70:
62:
936:
1036:
1001:
803:
684:
669:
500:
442:
384:
241:
231:
220:
160:
26:
23:
Chemical reaction that removes a carboxyl group and releases carbon dioxide
785:"Ketonization of Carboxylic Acids by Decarboxylation: Mechanism and Scope"
718:
699:
620:
343:
227:
1186:
536:
518:
464:
460:
449:
347:
274:
983:
1107:
1071:
545:
532:
491:
487:
152:
119:
398:
as an electron donor. The decarboxylation can be depicted as such:
636:
568:
554:
527:
523:
482:
478:
351:
290:
223:
680:
612:
Synthesis of saturated fatty acids via fatty acid synthase II in
130:
129:
Overall, decarboxylation depends upon stability of the carbanion
69:
to a compound. Enzymes that catalyze decarboxylations are called
966:
Weaver, J. D.; Recio, A.; Grenning, A. J.; Tunge, J. A. (2011).
550:
514:
496:
339:
327:
252:
235:
1014:
841:
651:. When cannabis is heated in vacuum, the decarboxylation of
541:
453:
323:
679:
In beverages stored for long periods, very small amounts of
673:
640:
509:
213:
330:-mediated cleavage of the ester, forming the carboxylate.
89:
The term "decarboxylation" usually means replacement of a
888:"The Decarboxylation of Carboxylic Acids and their Salts"
965:
908:
Thorpe, J. F.; Kon, G. A. R. (1925). "Cyclopentanone".
1171:
698:
has been reported to catalyze the decarboxylation of
1148:"Data on Benzene in Soft Drinks and Other Beverages"
676:
in THCA and THC) to participate in decarboxylation.
643:
to a keto group when the alpha carbon is protonated.
354:(T:) is the active component for decarboxylation of
299:
are generally radical reactions. These include the
53:). Usually, decarboxylation refers to a reaction of
436:
375:T=C(OH)R + R'COOH → T! : + RC(O)CH(OH)R'
342:-coupled processes effect the decarboxylation of
315:is an unusual radical reductive decarboxylation.
234:, in which a pair of carboxylic acids combine to
208:and they allow keto acids serve as a stabilizing
1197:
687:by decarboxylation catalyzed by the presence of
843:Encyclopedia of Reagents for Organic Synthesis
874:Organic Synthesis: The disconnection approach
935:Wiley, Richard H.; Smith, Newton R. (1953).
717:
240:
163:) decarboxylate easily. Decarboxylation of
934:
326:. In this case, the reaction begins with
255:compounds, facilitate decarboxylation via
991:
907:
885:
560:Other decarboxylation reactions from the
383:promotes decarboxylation of amino acids.
196:Decarboxylations are an important in the
1043:
840:
630:
607:
226:) accelerate decarboxylation. A strong
25:
815:
813:
778:
776:
603:
143:, although the anion may not be a true
84:
1198:
694:The addition of catalytic amounts of
259:intermediates. Metals that catalyze
834:
810:
782:
773:
639:, and depends on conversion of the
281:, uncatalyzed decarboxylation of a
13:
333:
14:
1217:
1165:
1140:
1101:
1065:
1008:
959:
762:from the original on 2022-12-21
626:
277:decarboxylate. In the related
1134:10.1016/j.molstruc.2010.11.061
1114:Journal of Molecular Structure
1095:10.1016/j.molstruc.2010.11.061
1075:Journal of Molecular Structure
928:
901:
879:
867:
748:
711:
437:Decarboxylation of amino acids
265:decarboxylative cross-coupling
236:the eponymous functional group
155:, β‑nitriles, α‑
1:
705:
394:using the decarboxylation of
1029:10.1016/j.bioorg.2012.03.001
165:sodium chlorodifluoroacetate
7:
653:tetrahydrocannabinolic acid
202:acetoacetic ester synthesis
10:
1222:
823:. Organic Chemistry Portal
446:oxidative decarboxylations
297:Oxidative decarboxylations
149:electron-withdrawing group
73:or, the more formal term,
15:
821:"Malonic Ester Synthesis"
806:– via The Vespiary.
655:(THCA) appears to follow
953:10.15227/orgsyn.033.0062
922:10.15227/orgsyn.005.0037
851:10.1002/047084289X.rs058
577:pyruvate decarboxylation
261:cross-coupling reactions
206:Knoevenagel condensation
124:destructive distillation
16:Not to be confused with
320:Krapcho decarboxylation
1206:Substitution reactions
804:10.1002/ejoc.200400546
644:
616:
427:Fe=O + R'H → RCO
367:H → T=C(OH)R + CO
358:, including pyruvate:
313:Barton decarboxylation
245:
31:
1055:lipidlibrary.aocs.org
634:
611:
244:
145:chemical intermediate
29:
1017:Bioorganic Chemistry
657:first order kinetics
649:Tetrahydrocannabinol
604:Fatty acid synthesis
212:for carboxylic acid
184:Na → NaCl + CF
161:arylcarboxylic acids
85:In organic chemistry
65:, the addition of CO
1187:10.1246/cl.1986.893
1126:2011JMoSt.987...67P
1087:2011JMoSt.987...67P
727:, New York: Wiley,
396:alpha-ketoglutarate
381:Pyridoxal phosphate
322:starts with methyl
257:carboxylate complex
886:Jim Clark (2004).
645:
617:
301:Kolbe electrolysis
251:salts, especially
246:
32:
1175:Chemistry Letters
984:10.1021/cr1002744
941:Organic Syntheses
792:Eur. J. Org. Chem
562:citric acid cycle
110:H → RH + CO
39:chemical reaction
1213:
1191:
1190:
1169:
1163:
1162:
1160:
1159:
1150:. Archived from
1144:
1138:
1137:
1105:
1099:
1098:
1069:
1063:
1062:
1061:on 21 July 2011.
1047:
1041:
1040:
1012:
1006:
1005:
995:
978:(3): 1846–1913.
963:
957:
956:
937:"m-Nitrostyrene"
932:
926:
925:
905:
899:
898:
896:
895:
883:
877:
871:
865:
864:
838:
832:
831:
829:
828:
817:
808:
807:
789:
783:Renz, M (2005).
780:
771:
770:
768:
767:
752:
746:
745:
715:
474:phenylethylamine
432:
419:
393:
376:
371:
293:electrophile.
279:Hammick reaction
270:Upon heating in
249:Transition metal
210:protecting group
192:
142:
141:
140:
114:
96:
55:carboxylic acids
1221:
1220:
1216:
1215:
1214:
1212:
1211:
1210:
1196:
1195:
1194:
1170:
1166:
1157:
1155:
1146:
1145:
1141:
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1102:
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1049:
1048:
1044:
1013:
1009:
964:
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929:
906:
902:
893:
891:
884:
880:
872:
868:
861:
839:
835:
826:
824:
819:
818:
811:
787:
781:
774:
765:
763:
754:
753:
749:
735:
716:
712:
708:
629:
606:
439:
430:
426:
422:
418:
415:Fe{IV}=O + CO
414:
410:
406:
402:
392:
388:
374:
370:
366:
362:
356:alpha-ketoacids
336:
334:In biochemistry
309:Kochi reactions
289:that attacks a
191:
187:
183:
179:
175:
169:difluorocarbene
151:(e.g. β‑
139:
137:
136:
135:
133:
113:
109:
105:
94:
87:
68:
52:
41:that removes a
35:Decarboxylation
30:Decarboxylation
24:
21:
18:Decarbonylation
12:
11:
5:
1219:
1209:
1208:
1193:
1192:
1181:(6): 893–896.
1164:
1139:
1120:(1–3): 67–73.
1100:
1081:(1–3): 67–73.
1064:
1042:
1007:
958:
927:
900:
878:
866:
859:
833:
809:
798:(6): 979–988.
772:
747:
733:
709:
707:
704:
683:may form from
665:salicylic acid
661:Arrhenius' law
628:
625:
605:
602:
601:
600:
589:
583:oxalosuccinate
580:
558:
557:
548:
539:
530:
521:
512:
503:
494:
485:
476:
467:
438:
435:
434:
433:
428:
424:
420:
416:
412:
408:
404:
390:
378:
377:
372:
368:
364:
335:
332:
287:stable carbene
283:picolinic acid
194:
193:
189:
185:
181:
177:
138:
116:
115:
111:
107:
91:carboxyl group
86:
83:
75:carboxy-lyases
71:decarboxylases
66:
59:photosynthesis
50:
47:carbon dioxide
43:carboxyl group
22:
9:
6:
4:
3:
2:
1218:
1207:
1204:
1203:
1201:
1188:
1184:
1180:
1176:
1168:
1154:on 2008-03-26
1153:
1149:
1143:
1135:
1131:
1127:
1123:
1119:
1115:
1111:
1104:
1096:
1092:
1088:
1084:
1080:
1076:
1068:
1060:
1056:
1052:
1046:
1038:
1034:
1030:
1026:
1022:
1018:
1011:
1003:
999:
994:
989:
985:
981:
977:
973:
969:
962:
954:
950:
946:
942:
938:
931:
923:
919:
915:
911:
904:
889:
882:
875:
870:
862:
860:0-471-93623-5
856:
852:
848:
844:
837:
822:
816:
814:
805:
801:
797:
793:
786:
779:
777:
761:
757:
751:
744:
740:
736:
734:9780471854722
730:
726:
725:
720:
714:
710:
703:
701:
697:
696:cyclohexenone
692:
690:
689:ascorbic acid
686:
682:
677:
675:
671:
666:
662:
658:
654:
650:
642:
638:
633:
624:
622:
615:
610:
598:
594:
593:ketoglutarate
590:
588:
587:ketoglutarate
584:
581:
578:
574:
570:
567:
566:
565:
563:
556:
552:
549:
547:
543:
540:
538:
534:
531:
529:
525:
522:
520:
516:
513:
511:
507:
506:glutamic acid
504:
502:
498:
495:
493:
489:
486:
484:
480:
477:
475:
471:
470:phenylalanine
468:
466:
462:
459:
458:
457:
455:
451:
447:
444:
421:
401:
400:
399:
397:
386:
382:
373:
363:T: + RC(O)CO
361:
360:
359:
357:
353:
349:
345:
341:
331:
329:
325:
321:
316:
314:
310:
306:
302:
298:
294:
292:
288:
284:
280:
276:
273:
272:cyclohexanone
268:
266:
262:
258:
254:
250:
243:
239:
237:
233:
229:
225:
222:
217:
215:
211:
207:
203:
199:
174:
173:
172:
170:
166:
162:
158:
154:
150:
146:
132:
127:
125:
121:
104:
103:
102:
100:
99:hydrogen atom
92:
82:
80:
76:
72:
64:
63:carboxylation
60:
56:
48:
45:and releases
44:
40:
36:
28:
19:
1178:
1174:
1167:
1156:. Retrieved
1152:the original
1142:
1117:
1113:
1103:
1078:
1074:
1067:
1059:the original
1054:
1045:
1020:
1016:
1010:
975:
971:
961:
944:
940:
930:
913:
909:
903:
892:. Retrieved
881:
873:
869:
842:
836:
825:. Retrieved
795:
791:
764:. Retrieved
750:
723:
719:March, Jerry
713:
693:
685:benzoic acid
678:
670:alpha carbon
646:
627:Case studies
618:
613:
597:succinyl-CoA
559:
501:ethanolamine
443:biosynthetic
440:
379:
337:
317:
295:
269:
267:reaction.
247:
232:ketonization
221:zwitterionic
218:
195:
128:
117:
88:
61:, is called
34:
33:
890:. Chemguide
700:amino acids
621:malonyl-CoA
450:amino acids
344:malonyl-CoA
305:Hunsdiecker
275:amino acids
1158:2008-03-26
910:Org. Synth
894:2007-10-22
827:2007-10-26
766:2008-12-07
706:References
573:acetyl-CoA
537:putrescine
519:cadaverine
465:tryptamine
461:tryptophan
431:Fe + R'OH
348:acetyl-CoA
230:is key to
167:generates
159:acids, or
153:keto acids
972:Chem. Rev
743:642506595
564:include:
546:serotonin
533:ornithine
492:histamine
488:histidine
120:pyrolysis
97:) with a
79:EC number
1200:Category
1037:22534166
1023:: 2–14.
1002:21235271
760:Archived
721:(1985),
637:cannabis
569:pyruvate
555:dopamine
528:agmatine
524:arginine
483:tyramine
479:tyrosine
352:Thiamine
291:carbonyl
285:gives a
224:tautomer
81:4.1.1).
1122:Bibcode
1083:Bibcode
993:3116714
876:, 2 ed.
681:benzene
614:E. coli
441:Common
411:→ RCO
403:RC(O)CO
311:. The
204:. The
198:malonic
131:synthon
95:−C(O)OH
1035:
1000:
990:
947:: 62.
916:: 37.
857:
741:
731:
551:L-DOPA
515:lysine
497:serine
454:amines
385:Flavin
340:Biotin
328:halide
324:esters
253:copper
788:(PDF)
585:to α-
575:(see
542:5-HTP
456:are:
407:Fe O
303:and
214:enols
188:+ CO
157:nitro
37:is a
1033:PMID
998:PMID
855:ISBN
796:2005
739:OCLC
729:ISBN
674:enol
641:enol
510:GABA
228:base
216:.
200:and
180:ClCO
122:and
1183:doi
1130:doi
1118:987
1091:doi
1079:987
1025:doi
988:PMC
980:doi
976:111
949:doi
918:doi
847:doi
800:doi
595:to
571:to
553:to
544:to
535:to
526:to
517:to
508:to
499:to
490:to
481:to
472:to
463:to
452:to
448:of
423:RCO
346:to
126:.
106:RCO
49:(CO
1202::
1179:15
1177:.
1128:.
1116:.
1112:.
1089:.
1077:.
1053:.
1031:.
1021:43
1019:.
996:.
986:.
974:.
970:.
945:33
943:.
939:.
912:.
853:.
845:.
812:^
794:.
790:.
775:^
758:.
737:,
691:.
623:.
591:α-
350:.
238::
176:CF
171::
101::
1189:.
1185::
1161:.
1136:.
1132::
1124::
1097:.
1093::
1085::
1039:.
1027::
1004:.
982::
955:.
951::
924:.
920::
914:5
897:.
863:.
849::
830:.
802::
769:.
599:.
579:)
429:2
425:2
417:2
413:2
409:2
405:2
391:2
389:O
369:2
365:2
307:-
190:2
186:2
182:2
178:2
134:R
112:2
108:2
93:(
77:(
67:2
51:2
20:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
