28:
145:
349:
405:) with reduced activity compared to the acids. Decarboxylation, such as through heating done in most commercial oil processing, results in compounds with significantly reduced activity. It is said that the people of the
84:; anacardic acid is a mixture of saturated and unsaturated molecules. The exact mixture depends on the species of the plant. The 15-carbon unsaturated side chain compound found in the cashew plant is lethal to
560:
393:, the acne bacterium. Eichbaum claims that a solution of one part anacardic acid to 200,000 parts water to as low as one part in 2,000,000 is lethal to Gram-positive bacteria in 15 minutes
68:. Anacardic acid is a yellow liquid. It is partially miscible with ethanol and ether, but nearly immiscible with water. Chemically, anacardic acid is a mixture of several closely related
978:
Muroi H, Kubo I (April 1996). "Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant
Staphylococcus aureus".
362:
943:
Schultz DJ, Olsen C, Cobbs GA, Stolowich NJ, Parrott MM (October 2006). "Bioactivity of anacardic acid against colorado potato beetle (Leptinotarsa decemlineata) larvae".
715:
Eichbaum FW (1946). "Biological properties of anacardic acid (O- pentadeca dienylsalicylic acid) and related compounds. General discussion-bactericidal action".
1084:
282:
520:
104:
209:
672:
498:
81:
65:
36:
441:
was published in 1847. It was later found to be a mixture rather than one chemical, sometimes the plural anacardic acids is used.
781:
801:
369:
761:
Patel NM, Patel MS (1936). "Cashew-nut shell oil and a study of the changes produced in the oil by the action of heat".
734:
Himejima M, Kubo I (1991). "Antibacterial agents from the cashew
Anacardium occidentale (Anacardiaceae) nutshell oil".
494:
539:
387:, the tooth decay bacterium, in test tube experiments. The number of unsaturated bonds was not material against
1079:
1074:
240:
246:
763:
Journal of the
University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences, Medicine
688:
Kubo I, Muroi H, Himejima M (1993). "Structure - Antibacterial activity relationships of anacardic acids".
418:
112:
85:
52:
489:
There is also a suspicion that inhibiting anacardic acids may arrest the growth of cancer tumors such as
229:
1089:
859:
Kubo I, Muroi H, Himejima M (October 1992). "Antibacterial activity of totarol and its potentiation".
1069:
894:
Bakhos-Douaihy D, Desmaze C, Jeitany M, Gauthier LR, Biard D, Junier MP, et al. (January 2019).
627:
383:
157:
406:
389:
175:
426:
645:
547:
1046:
995:
960:
925:
876:
668:
596:
502:
1036:
1026:
987:
952:
915:
907:
868:
841:
810:
743:
697:
635:
588:
305:
69:
185:
508:
Anacardic acid (2-hydroxy-6-alkylbenzoic acid) provides resistance to small pest insects (
429:, which are used as curing agents for the durable epoxy coatings used on concrete floors.
425:, which is used for resins, coatings, and frictional materials. Cardanol is used to make
1015:"Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells"
631:
1041:
1014:
991:
920:
895:
340:
73:
47:
27:
1063:
896:"ALT cancer cells are specifically sensitive to lysine acetyl transferase inhibition"
592:
490:
92:
268:
144:
649:
513:
458:
398:
100:
121:
911:
814:
543:
477:
328:
17:
845:
401:
in 30 minutes. Heating these anacardic acids converts them to the alcohols (
1050:
964:
929:
1031:
999:
880:
600:
467:
462:
450:
422:
402:
57:
872:
747:
701:
437:
The first chemical analysis of the oil of the cashew nut shell from the
381:
The side chain with three unsaturated bonds was the most active against
616:"Olefinic Nature of Anacardic Acid from Indian Cashew-nut Shell Liquid"
527:
472:
255:
956:
481:
trees is synergistic with anacardic acid in its bactericidal effects.
640:
615:
509:
421:(CNSL), and finds use in the chemical industry for the production of
220:
108:
829:
339:
Except where otherwise noted, data are given for materials in their
454:
208:
198:
116:
77:
32:
26:
96:
61:
830:"Ueber die eigenthümlichen Bestandtheile der Anacardiumfrüchte"
788:. Horticulture & Landscape Architecture, Purdue University.
80:
chain that has 15 or 17 carbon atoms. The alkyl group may be
561:
List of phytochemicals and foods in which they are prominent
579:
Rosen T, Fordice DB (April 1994). "Cashew nut dermatitis".
50:, chemical compounds found in the shell of the cashew nut (
409:(now Ghana) use cashew leaves and bark for a toothache.
497:
by anacardic acid was shown to make cancer cells using
357:
397:. Somewhat higher ratios killed tubercle bacteria of
1013:
Rajendran P, Ho E, Williams DE, Dashwood RH (2011).
799:Tullo AH (September 8, 2008). "A Nutty Chemical".
546:shell liquid, and sensitizer of cancer cells to
267:
184:
31:General structure of anacardic acids. R is an
8:
945:Journal of Agricultural and Food Chemistry
736:Journal of Agricultural and Food Chemistry
690:Journal of Agricultural and Food Chemistry
132:
107:. It is primarily found in foods such as
1040:
1030:
919:
639:
417:Anacardic acid is the main component of
290:C=CCC=CCC=CCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
571:
287:
245:
35:chain of variable length, which may be
542:(6-PDSA), a potent HAT inhibitor from
786:Handbook of Energy Crops. unpublished
228:
129:Experimental antibacterial properties
7:
667:. Amsterdam: Elsevier. p. 132.
499:alternative lengthening of telomeres
1085:Histone Acetyltransferase Inhibitor
980:The Journal of Applied Bacteriology
449:Anacardic acid is synergistic with
258:
66:urushiol-induced contact dermatitis
992:10.1111/j.1365-2672.1996.tb03233.x
25:
614:Paul VJ, Yeddanapalli LM (1954).
834:Annalen der Chemie und Pharmacie
782:"Cashew plants in folk medicine"
593:10.1097/00007611-199404000-00026
347:
143:
526:(MRSA) cells more rapidly than
343:(at 25 °C , 100 kPa).
717:Memórias do Instituto Butantan
665:Integrative plant biochemistry
60:, they also cause an allergic
1:
802:Chemical and Engineering News
333:342.4718 g/mol
95:, it is also active against
861:Journal of Natural Products
540:6-pentadecyl salicylic acid
134:Anacardic acid (C15:3, all-
1106:
64:rash on contact, known as
912:10.18632/oncotarget.26616
815:10.1021/cen-v086n033.p026
337:
298:
278:
168:
156:
151:
142:
111:nuts, cashew apples, and
846:10.1002/jlac.18470630202
581:Southern Medical Journal
495:lysine acetyltransferase
485:Other and potential uses
162:2-Hydroxy-6-benzoic acid
82:saturated or unsaturated
37:saturated or unsaturated
534:List of anacardic acids
663:Romeo JT, ed. (2006).
521:methicillin-resistant
439:Anacardium occidentale
419:cashew nutshell liquid
86:Gram-positive bacteria
53:Anacardium occidentale
40:
1032:10.1186/1868-7083-3-4
523:Staphylococcus aureus
519:Anacardic acid kills
72:. Each consists of a
30:
1019:Clinical Epigenetics
384:Streptococcus mutans
158:Preferred IUPAC name
76:substituted with an
873:10.1021/np50088a008
828:Städeler J (1847).
748:10.1021/jf00002a039
702:10.1021/jf00030a036
632:1954Natur.174..604P
390:Cutibacterium acnes
139:
138:, major component)
113:cashew nutshell oil
56:). An acid form of
548:ionizing radiation
501:more sensitive to
370:Infobox references
133:
41:
957:10.1021/jf061481u
951:(20): 7522–7529.
867:(10): 1436–1440.
696:(6): 1016–1019 .
674:978-0-08-045125-1
493:. Inhibition of
453:from the seed of
378:Chemical compound
376:
375:
210:Interactive image
70:organic compounds
16:(Redirected from
1097:
1055:
1054:
1044:
1034:
1010:
1004:
1003:
975:
969:
968:
940:
934:
933:
923:
891:
885:
884:
856:
850:
849:
825:
819:
818:
796:
790:
789:
780:Duke JA (1983).
777:
771:
770:
769:(pt 2): 114–131.
758:
752:
751:
731:
725:
724:
712:
706:
705:
685:
679:
678:
660:
654:
653:
643:
641:10.1038/174604a0
611:
605:
604:
576:
360:
354:
351:
350:
306:Chemical formula
271:
260:
249:
232:
212:
188:
147:
140:
99:, some insects,
21:
1105:
1104:
1100:
1099:
1098:
1096:
1095:
1094:
1080:Salicylic acids
1075:Phenolic lipids
1060:
1059:
1058:
1012:
1011:
1007:
977:
976:
972:
942:
941:
937:
893:
892:
888:
858:
857:
853:
827:
826:
822:
798:
797:
793:
779:
778:
774:
760:
759:
755:
742:(2): 418–421 .
733:
732:
728:
714:
713:
709:
687:
686:
682:
675:
662:
661:
657:
613:
612:
608:
578:
577:
573:
569:
557:
536:
487:
475:in the bark of
465:from green tea
447:
435:
415:
413:Industrial uses
379:
372:
367:
366:
365: ?)
356:
352:
348:
344:
322:
318:
314:
308:
294:
291:
286:
285:
274:
261:
235:
215:
202:
191:
178:
164:
163:
131:
93:tooth abscesses
48:phenolic lipids
44:Anacardic acids
23:
22:
15:
12:
11:
5:
1103:
1101:
1093:
1092:
1087:
1082:
1077:
1072:
1062:
1061:
1057:
1056:
1005:
986:(4): 387–394.
970:
935:
906:(7): 773–784.
886:
851:
840:(2): 137–164.
820:
791:
772:
753:
726:
707:
680:
673:
655:
606:
587:(4): 543–546.
570:
568:
565:
564:
563:
556:
553:
552:
551:
535:
532:
486:
483:
446:
443:
434:
431:
414:
411:
377:
374:
373:
368:
346:
345:
341:standard state
338:
335:
334:
331:
325:
324:
320:
316:
312:
309:
304:
301:
300:
296:
295:
293:
292:
289:
281:
280:
279:
276:
275:
273:
272:
264:
262:
254:
251:
250:
247:anacardic+acid
243:
237:
236:
234:
233:
225:
223:
217:
216:
214:
213:
205:
203:
196:
193:
192:
190:
189:
181:
179:
174:
171:
170:
166:
165:
161:
160:
154:
153:
149:
148:
130:
127:
115:, but also in
74:salicylic acid
24:
18:Anacardic acid
14:
13:
10:
9:
6:
4:
3:
2:
1102:
1091:
1088:
1086:
1083:
1081:
1078:
1076:
1073:
1071:
1068:
1067:
1065:
1052:
1048:
1043:
1038:
1033:
1028:
1024:
1020:
1016:
1009:
1006:
1001:
997:
993:
989:
985:
981:
974:
971:
966:
962:
958:
954:
950:
946:
939:
936:
931:
927:
922:
917:
913:
909:
905:
901:
897:
890:
887:
882:
878:
874:
870:
866:
862:
855:
852:
847:
843:
839:
835:
831:
824:
821:
816:
812:
809:(36): 26–27.
808:
804:
803:
795:
792:
787:
783:
776:
773:
768:
764:
757:
754:
749:
745:
741:
737:
730:
727:
722:
718:
711:
708:
703:
699:
695:
691:
684:
681:
676:
670:
666:
659:
656:
651:
647:
642:
637:
633:
629:
626:(4430): 604.
625:
621:
617:
610:
607:
602:
598:
594:
590:
586:
582:
575:
572:
566:
562:
559:
558:
554:
549:
545:
541:
538:
537:
533:
531:
529:
525:
524:
517:
515:
511:
506:
504:
500:
496:
492:
491:breast cancer
484:
482:
480:
479:
474:
470:
469:
464:
460:
456:
452:
444:
442:
440:
432:
430:
428:
427:phenalkamines
424:
420:
412:
410:
408:
404:
400:
396:
392:
391:
386:
385:
371:
364:
359:
342:
336:
332:
330:
327:
326:
310:
307:
303:
302:
297:
288:
284:
277:
270:
266:
265:
263:
257:
253:
252:
248:
244:
242:
239:
238:
231:
227:
226:
224:
222:
219:
218:
211:
207:
206:
204:
200:
195:
194:
187:
183:
182:
180:
177:
173:
172:
167:
159:
155:
150:
146:
141:
137:
128:
126:
124:
123:
118:
114:
110:
106:
102:
98:
94:
91:Folk use for
89:
87:
83:
79:
75:
71:
67:
63:
59:
55:
54:
49:
45:
38:
34:
29:
19:
1090:Plant toxins
1022:
1018:
1008:
983:
979:
973:
948:
944:
938:
903:
899:
889:
864:
860:
854:
837:
833:
823:
806:
800:
794:
785:
775:
766:
762:
756:
739:
735:
729:
720:
716:
710:
693:
689:
683:
664:
658:
623:
619:
609:
584:
580:
574:
522:
518:
514:spider mites
507:
488:
476:
466:
459:Umbelliferae
448:
438:
436:
416:
399:tuberculosis
394:
388:
382:
380:
230:ChEMBL455368
169:Identifiers
135:
120:
101:tuberculosis
90:
51:
43:
42:
1070:Antiseptics
299:Properties
125:geraniums.
122:Pelargonium
1064:Categories
900:Oncotarget
567:References
544:cashew nut
478:Podocarpus
407:Gold Coast
329:Molar mass
197:3D model (
186:11034-77-8
176:CAS Number
503:radiation
445:Synergies
403:cardanols
1051:22247744
1025:(1): 4.
965:17002417
930:30774779
723:: 71–86.
555:See also
468:in vitro
463:linalool
451:anethole
423:cardanol
395:in vitro
58:urushiol
1042:3255482
1000:8849640
921:6366824
881:1453180
650:4249027
628:Bibcode
601:8153790
528:totarol
473:totarol
433:History
363:what is
361: (
323:
269:9875131
256:PubChem
1049:
1039:
998:
963:
928:
918:
879:
671:
648:
620:Nature
599:
510:aphids
471:. The
461:) and
358:verify
355:
283:SMILES
221:ChEMBL
152:Names
117:mangos
109:cashew
103:, and
646:S2CID
455:anise
199:JSmol
78:alkyl
33:alkyl
1047:PMID
996:PMID
961:PMID
926:PMID
877:PMID
669:ISBN
597:PMID
512:and
241:MeSH
119:and
105:MRSA
97:acne
62:skin
46:are
1037:PMC
1027:doi
988:doi
953:doi
916:PMC
908:doi
869:doi
842:doi
811:doi
744:doi
698:doi
636:doi
624:174
589:doi
516:).
259:CID
1066::
1045:.
1035:.
1021:.
1017:.
994:.
984:80
982:.
959:.
949:54
947:.
924:.
914:.
904:10
902:.
898:.
875:.
865:55
863:.
838:63
836:.
832:.
807:86
805:.
784:.
765:.
740:39
738:.
721:19
719:.
694:41
692:.
644:.
634:.
622:.
618:.
595:.
585:87
583:.
530:.
505:.
317:30
313:22
88:.
1053:.
1029::
1023:3
1002:.
990::
967:.
955::
932:.
910::
883:.
871::
848:.
844::
817:.
813::
767:5
750:.
746::
704:.
700::
677:.
652:.
638::
630::
603:.
591::
550:.
457:(
353:N
321:3
319:O
315:H
311:C
201:)
136:Z
39:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
