264:
189:
27:
403:
550:
of this simple natural product was performed by
Crawford et al. in 1956, but is of limited contemporary synthetic interest. A variety of acetosyringone analogues are available, including some which are covalent inactivators of cellular processes that involve acetosyringone.
491:
is used by these soil bacteria to infect plants, via its encoding for a receptor for acetosyringone and other phenolic phytochemicals exuded by plant wounds. This compound also allows higher transformation efficiency in plants, as shown in
559:
Acetosyringone does not dissolve well in water. Although it has a melting point of about 125 degree
Celsius, it is not wise to autoclave acetosyringone along with the medium used for (for example) plant infiltration by microbes.
465:
Historically, this substance has been best known for its involvement in plant-pathogen recognition, especially its role as a signal attracting and transforming unique, oncogenic bacteria in genus
887:
Estela Flores-Gómez; Lidia Gómez-Silva; Roberto Ruiz-Medrano; Beatriz
Xoconostle-Cázares (2008). "Role of acetosyringone in the accumulation of a set of RNAs in the arbuscular mycorrhiza fungus
416:
710:
Sheikholeslam, Shahla N.; Weeks, Donald P. (1987). "Acetosyringone promotes high efficiency transformation of
Arabidopsis thaliana explants by Agrobacterium tumefaciens".
825:
Aldrich, J.R.; Blum, M.S.; Duffey, S.S.; Fales, H.M. (1976). "Male specific natural products in the bug, Leptoglossus phyllopus: Chemistry and possible function".
303:
457:/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes.
852:
Aldrich, J. R.; Blum, M. S.; Fales, H. M. (1979). "Species-specific natural products of adult male leaf-footed bugs (Hemiptera: Heteroptera)".
964:
753:
Agostini, Sylvia; Desjobert, Jean-Marie; Pergent, Gérard (1998). "Distribution of phenolic compounds in the seagrass
Posidonia oceanica".
630:
Baker C. Jacyn; Mock Norton M.; Whitaker Bruce D.; Roberts Daniel P.; Rice
Clifford P.; Deahl Kenneth L.; Aver'Yanov Andrey A. (2005).
99:
278:
974:
106:
631:
423:
26:
221:
242:
969:
984:
813:
481:
570:
487:
184:
526:
146:
39:
979:
539:
450:
259:
65:
869:
735:
671:"Sequence analysis of the vir-region from Agrobacterium tumefaciens octopine Ti plasmid pTi15955"
501:
669:
Schrammeijer, B.; Beijersbergen, A; Idler, KB; Melchers, LS; Thompson, DV; Hooykaas, PJ (2000).
908:
727:
692:
651:
939:
900:
861:
834:
762:
719:
682:
643:
331:
230:
166:
590:
547:
442:
75:
781:
263:
188:
595:
585:
439:
394:
126:
766:
958:
838:
600:
580:
514:
496:-mediated transformation procedures, and so is of importance in plant biotechnology.
467:
382:
372:
177:
873:
780:
Naveed Iqbal Raja; Asghari Bano; Hamid Rashid; Zubeda
Chaudry; Noshin Ilyas (2010).
739:
446:
210:
687:
670:
506:
647:
534:
476:
359:
157:
912:
731:
696:
655:
904:
786:-mediated Transformation Protocol For Integration Of XA21 Gene In Wheat (
605:
575:
865:
723:
610:
505:
and a wide variety of other plants. It is secreted at wounded sites of
197:
517:
lack this wound response, which is considered the limiting factor in
454:
137:
944:
927:
393:
Except where otherwise noted, data are given for materials in their
287:
InChI=1S/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H3
117:
105:
98:
88:
814:
Acetosyringone on www.pherobase.com, the pheromones data base
632:"Involvement of acetosyringone in plant-pathogen recognition"
247:
524:
The compound is also produced by the male leaffooted bug (
411:
533:
In vitro studies show that acetosyringone increases
636:
926:L. W. Crawford; E. O. Eaton; J. M. Pepper (1956).
209:
74:
8:
377:125.5 °C (257.9 °F; 398.6 K)
44:1-(4-Hydroxy-3,5-dimethoxyphenyl)ethan-1-one
521:-mediated gene transformation in monocots.
262:
187:
165:
18:
943:
928:"An Improved Synthesis of Acetosyringone"
686:
513:-mediated gene transformation in dicots.
229:
530:) and used in its communication system.
453:. It was first described in relation to
622:
308:
283:
258:
387:335 °C (635 °F; 608 K)
178:
290:Key: OJOBTAOGJIWAGB-UHFFFAOYSA-N
145:
125:
7:
499:Acetosyringone can also be found in
445:and a chemical compound related to
200:
14:
401:
343:
25:
397:(at 25 °C , 100 kPa).
675:Journal of Experimental Botany
461:Occurrence and biological role
349:
337:
1:
932:Canadian Journal of Chemistry
767:10.1016/S0031-9422(97)01118-7
509:. This compound enhances the
965:O-methylated natural phenols
839:10.1016/0022-1910(76)90094-9
827:Journal of Insect Physiology
311:CC(=O)C1=CC(=C(C(=C1)OC)O)OC
854:Journal of Chemical Ecology
1001:
893:International Microbiology
688:10.1093/jexbot/51.347.1167
648:10.1016/j.bbrc.2004.12.153
482:Agrobacterium tumefaciens
391:
324:
316:O=C(c1cc(OC)c(O)c(OC)c1)C
299:
274:
58:
50:
38:
33:
24:
571:Phenolic content in wine
555:Chemical characteristics
537:formation in the fungus
488:Agrobacterium rhizogenes
975:Skin chemical irritants
712:Plant Molecular Biology
527:Leptoglossus phyllopus
485:and the Ri plasmid of
905:10.2436/20.1501.01.72
40:Preferred IUPAC name
889:Glomus intraradices
540:Glomus intraradices
451:2,6-dimethoxyphenol
367: g·mol
21:
866:10.1007/BF00987687
724:10.1007/BF00021308
681:(347): 1167–1169.
502:Posidonia oceanica
424:Infobox references
19:
970:Insect pheromones
938:(11): 1562–1566.
788:Triticum aestivum
432:Chemical compound
430:
429:
243:CompTox Dashboard
107:Interactive image
100:Interactive image
16:Chemical compound
992:
985:Aromatic ketones
950:
949:
947:
923:
917:
916:
884:
878:
877:
849:
843:
842:
833:(9): 1201–1206.
822:
816:
811:
805:
804:
794:
777:
771:
770:
750:
744:
743:
707:
701:
700:
690:
666:
660:
659:
627:
414:
408:
405:
404:
366:
351:
345:
339:
332:Chemical formula
267:
266:
251:
249:
233:
213:
202:
191:
180:
169:
149:
129:
109:
102:
78:
29:
22:
1000:
999:
995:
994:
993:
991:
990:
989:
955:
954:
953:
945:10.1139/v56-204
925:
924:
920:
886:
885:
881:
851:
850:
846:
824:
823:
819:
812:
808:
803:(5): 3613–3631.
792:
779:
778:
774:
752:
751:
747:
709:
708:
704:
668:
667:
663:
629:
628:
624:
620:
615:
591:Sinapyl alcohol
566:
557:
548:total synthesis
463:
443:natural product
433:
426:
421:
420:
419: ?)
410:
406:
402:
398:
364:
354:
348:
342:
334:
320:
317:
312:
307:
306:
295:
292:
291:
288:
282:
281:
270:
252:
245:
236:
216:
203:
172:
152:
132:
112:
92:
81:
68:
54:
53:Acetosyringenin
46:
45:
20:Acetosyringone
17:
12:
11:
5:
998:
996:
988:
987:
982:
977:
972:
967:
957:
956:
952:
951:
918:
899:(4): 275–282.
879:
844:
817:
806:
772:
761:(4): 611–617.
755:Phytochemistry
745:
718:(4): 291–298.
702:
661:
642:(1): 130–136.
621:
619:
616:
614:
613:
608:
603:
598:
596:Sinapinic acid
593:
588:
586:Syringaldehyde
583:
578:
573:
567:
565:
562:
556:
553:
515:Monocotyledons
494:A. tumefaciens
462:
459:
436:Acetosyringone
431:
428:
427:
422:
400:
399:
395:standard state
392:
389:
388:
385:
379:
378:
375:
369:
368:
362:
356:
355:
352:
346:
340:
335:
330:
327:
326:
322:
321:
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315:
313:
310:
302:
301:
300:
297:
296:
294:
293:
289:
286:
285:
277:
276:
275:
272:
271:
269:
268:
255:
253:
241:
238:
237:
235:
234:
226:
224:
218:
217:
215:
214:
206:
204:
196:
193:
192:
182:
174:
173:
171:
170:
162:
160:
154:
153:
151:
150:
142:
140:
134:
133:
131:
130:
122:
120:
114:
113:
111:
110:
103:
95:
93:
86:
83:
82:
80:
79:
71:
69:
64:
61:
60:
56:
55:
52:
48:
47:
43:
42:
36:
35:
31:
30:
15:
13:
10:
9:
6:
4:
3:
2:
997:
986:
983:
981:
978:
976:
973:
971:
968:
966:
963:
962:
960:
946:
941:
937:
933:
929:
922:
919:
914:
910:
906:
902:
898:
894:
890:
883:
880:
875:
871:
867:
863:
859:
855:
848:
845:
840:
836:
832:
828:
821:
818:
815:
810:
807:
802:
798:
791:
789:
785:
784:Agrobacterium
776:
773:
768:
764:
760:
756:
749:
746:
741:
737:
733:
729:
725:
721:
717:
713:
706:
703:
698:
694:
689:
684:
680:
676:
672:
665:
662:
657:
653:
649:
645:
641:
637:
633:
626:
623:
617:
612:
609:
607:
604:
602:
601:Sinapaldehyde
599:
597:
594:
592:
589:
587:
584:
582:
581:Syringic acid
579:
577:
574:
572:
569:
568:
563:
561:
554:
552:
549:
544:
542:
541:
536:
531:
529:
528:
522:
520:
519:Agrobacterium
516:
512:
511:Agrobacterium
508:
504:
503:
497:
495:
490:
489:
484:
483:
478:
474:
470:
469:
468:Agrobacterium
460:
458:
456:
452:
448:
444:
441:
437:
425:
418:
413:
396:
390:
386:
384:
383:Boiling point
381:
380:
376:
374:
373:Melting point
371:
370:
363:
361:
358:
357:
336:
333:
329:
328:
323:
314:
309:
305:
298:
284:
280:
273:
265:
261:
260:DTXSID2062454
257:
256:
254:
244:
240:
239:
232:
228:
227:
225:
223:
220:
219:
212:
208:
207:
205:
199:
195:
194:
190:
186:
183:
181:
179:ECHA InfoCard
176:
175:
168:
164:
163:
161:
159:
156:
155:
148:
144:
143:
141:
139:
136:
135:
128:
124:
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116:
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108:
104:
101:
97:
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90:
85:
84:
77:
73:
72:
70:
67:
63:
62:
57:
49:
41:
37:
32:
28:
23:
935:
931:
921:
896:
892:
888:
882:
857:
853:
847:
830:
826:
820:
809:
800:
796:
787:
783:
775:
758:
754:
748:
715:
711:
705:
678:
674:
664:
639:
635:
625:
558:
545:
538:
532:
525:
523:
518:
510:
507:dicotyledons
500:
498:
493:
486:
480:
475:gene on the
472:
466:
464:
447:acetophenone
435:
434:
147:ChEMBL224146
59:Identifiers
51:Other names
797:Pak. J. Bot
782:"Improving
535:mycorrhizae
325:Properties
185:100.017.828
980:Vanilloids
959:Categories
618:References
477:Ti plasmid
360:Molar mass
231:866P45Y84S
158:ChemSpider
127:CHEBI:2404
87:3D model (
66:CAS Number
860:: 53–62.
76:2478-38-8
913:19204900
874:34346907
740:32005770
732:24301191
697:10948245
656:15670760
606:Sinapine
576:Syringol
564:See also
440:phenolic
611:Canolol
471:. The
417:what is
415: (
365:196.202
198:PubChem
911:
872:
738:
730:
695:
654:
455:lignan
412:verify
409:
304:SMILES
138:ChEMBL
34:Names
870:S2CID
793:(PDF)
736:S2CID
438:is a
279:InChI
211:17198
167:16280
118:ChEBI
89:JSmol
909:PMID
790:L.)"
728:PMID
693:PMID
652:PMID
473:virA
449:and
222:UNII
940:doi
901:doi
891:".
862:doi
835:doi
763:doi
720:doi
683:doi
644:doi
640:328
479:of
248:EPA
201:CID
961::
936:34
934:.
930:.
907:.
897:11
895:.
868:.
856:.
831:22
829:.
801:42
799:.
795:.
759:48
757:.
734:.
726:.
714:.
691:.
679:51
677:.
673:.
650:.
638:.
634:.
546:A
543:.
347:12
341:10
948:.
942::
915:.
903::
876:.
864::
858:5
841:.
837::
769:.
765::
742:.
722::
716:8
699:.
685::
658:.
646::
407:Y
353:4
350:O
344:H
338:C
250:)
246:(
91:)
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