269:
194:
33:
926:
24:
1334:
735:
450:
701:
dyestuffs are formed. The mono-amino derivatives or eurhodines are obtained when the arylmonamines are condensed with orthoamino azo compounds; by condensing quinone dichlorimide or para-nitrosodimethyl aniline with monamines containing a free para position, or by oxidizing
906:. Two molecules of this chorismate-derived intermediate are then brought together in a diagonally-symmetrical fashion to form the basic phenazine scaffold. Sequential modifications then lead to a variety of phenazine with differing
1144:
McDonald, M., D. V. Mavrodi; et al. (2001). "Phenazine biosynthesis in
Pseudomonas fluorescens: Branchpoint from the primary shikimate biosynthetic pathway and role of phenazine-1,6-dicarboxylic acid".
1249:
Beifuss, Uwe; Tietze, Mario; Bäumer, Sebastian; Deppenmeier, Uwe (2000-07-17). "Methanophenazine: Structure, Total
Synthesis, and Function of a New Cofactor from Methanogenic Archaea".
463:
867:
patients. Similarly, phenazine-1-carboxylic acid, produced by a number of
Pseudomonads, increases survival in soil environments and has been shown to be essential for the
1181:
318:
787:
of dimethylparaphenylene diatnine with metatoluylene diamine. It crystallizes in orange-red needles and its alcoholic solution fluoresces strongly. It dyes
1354:
890:
in other organisms. Methanophenazine is only known phenazine of non-bacterial origin and also is the only phenazine that engages in primary metabolisms.
783:-toluylenediamine gives toluylene blue. This indamine is formed as an intermediate product and passing into the red when boiled; and also by the
1313:
1120:
966:
831:
The known biological sources of phenazine compounds are mostly bacterial in nature. Some of the genera known to produce phenazines include
1349:
1048:"Metabolism and function of phenazines in bacteria: impacts on the behavior of bacteria in the environment and biotechnological processes"
1002:
283:
1262:
882:) is involved in primary metabolisms and are important electron carriers. Methanophenazine acts as the functional equivalent of
470:
226:
1196:
773:
247:
950:
853:
have been implicated in the virulence and competitive fitness of producing organisms. For example, the phenazine
32:
23:
111:
1204:
868:
742:
Many aminophenazines are prominent dyes. Two of the first synthetic dyes are aminophenazines, these include
189:
859:
549:
151:
1175:
605:
613:
45:
1376:
947:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
915:
907:
845:
264:
77:
1371:
762:
682:
609:
581:
919:
1309:
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1116:
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998:
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1155:
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990:
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875:
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711:
703:
686:
647:
560:
486:
413:
341:
235:
864:
766:
171:
1197:"Bacterial community morphogenesis is intimately linked to the intracellular redox state"
650:
are obtained. The azines are mostly yellow in color, distill unchanged and are stable to
702:
ortho-hydroxydiaminodipbenylamines. They are yellowish-red solids, which behave as weak
268:
193:
131:
87:
1226:
1080:
1047:
925:
903:
441:
1112:
548:
Classically phenazine are prepared by the reaction of nitrobenzene and aniline in the
1365:
1345:
1340:
899:
677:, which are closely related to the phthaleins, are formed by the condensation of the
591:
537:
517:
402:
392:
182:
887:
839:
816:
667:
655:
633:
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1300:, vol. 244, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 77–113,
994:
215:
1019:
958:
833:
796:
758:
754:
429:
1195:
Dietrich LE, Okegbe C, Price-Whelan A, Sakhtah H, Hunter RC, Newman DK (2013).
1063:
883:
879:
874:
While bacterial phenazines are principally involved in secondary metabolisms,
820:
707:
571:
506:
364:
162:
1358:. Vol. 21 (11th ed.). Cambridge University Press. pp. 364–365.
1270:
1071:
911:
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784:
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10.1002/1521-3773(20000717)39:14<2470::aid-anie2470>3.0.co;2-r
1130:
747:
743:
698:
694:
663:
629:
521:
509:
1217:
1105:
Occurrence, biochemistry, and physiology of phenazine pigment production
734:
651:
621:
567:
533:
529:
382:
202:
1159:
812:
792:
719:
632:, and by the decomposition of ortho-anilido-(-toluidido- et cetera)-
557:
142:
1107:. Advances in Microbial Physiology. Vol. 27. pp. 211–275.
666:. It dissolves in concentrated sulfuric acid with a yellowish-green
440:
Except where otherwise noted, data are given for materials in their
1305:
1294:"Methanophenazine and Other Natural Biologically Active Phenazines"
761:(dimethyldiaminotoluphenazine). It is obtained by the oxidation of
757:
diaminophenazine is the parent substance of the important dyestuff
1339:
This article incorporates text from a publication now in the
733:
690:
678:
122:
110:
100:
1292:
Beifuss, Uwe; Tietze, Mario (2005-01-26), Mulzer, Johann (ed.),
788:
637:
292:
InChI=1S/C12H8N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
302:
InChI=1/C12H8N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
513:
924:
576:
oxidation of dihydrophenazine, which is prepared by heating
252:
718:
the amino group is replaced by the hydroxyl group and the
407:
357.2 °C (675.0 °F; 630.3 K) at 760 mmHg
815:
of phenazine, to which it bears the same relation that
532:
in yellow needles, which are only sparingly soluble in
458:
772:
In a related process, oxidation of a cold mixture of
863:
contributes to its ability to colonise the lungs of
1046:Pierson, Leland S.; Pierson, Elizabeth A. (2010).
397:174–177 °C (345–351 °F; 447–450 K)
528:(and the closely related eurhodines). Phenazine
214:
86:
987:Ullmann's Encyclopedia of Industrial Chemistry
8:
1180:: CS1 maint: multiple names: authors list (
1103:Turner, J. M. & A. J. Messenger (1986).
795:a fine scarlet. It is known commercially as
434:160.3 °C (320.5 °F; 433.4 K)
590:oxidation of ortho-aminodiphenylamine with
540:dissolves it, forming a deep-red solution.
662:formation also taking place between these
267:
192:
170:
15:
1225:
1079:
910:. An example of phenazinic alkaloids are
643:If alkyl or aryl-ortho-diamines be used,
628:of an ortho-diamine in the presence of α-
604:The more complex phenazines, such as the
234:
898:Phenazine biosynthesis branches off the
685:in the presence of sulfuric acid. Their
1251:Angewandte Chemie International Edition
938:
323:
288:
263:
1173:
1052:Applied Microbiology and Biotechnology
689:are fine red dyes. By the entrance of
658:readily, forming alkyl azonium salts,
183:
980:
978:
295:Key: PCNDJXKNXGMECE-UHFFFAOYSA-N
150:
130:
7:
985:Horst Berneth (2012). "Azine Dyes".
512:, and the parent substance of many
377:yellow to brown crystalline powder
305:Key: PCNDJXKNXGMECE-UHFFFAOYAM
205:
14:
1332:
714:. When heated with concentrated
616:, may be prepared by condensing
448:
31:
22:
444:(at 25 °C , 100 kPa).
951:The Royal Society of Chemistry
1:
1298:Natural Products Synthesis II
1113:10.1016/S0065-2911(08)60306-9
995:10.1002/14356007.a03_213.pub3
871:activity of certain strains.
1018:Alexander R. Surrey (1955).
959:10.1039/9781849733069-FP001
1393:
1034:, vol. 3, p. 753
369:180.21 g/mol
1064:10.1007/s00253-010-2509-3
902:at a point subsequent to
878:in methanogenic archaea (
706:, their salts undergoing
552:. Other methods include:
438:
423:
334:
314:
279:
70:
56:
44:
39:
30:
21:
1355:Encyclopædia Britannica
1205:Journal of Bacteriology
989:. Weinheim: Wiley-VCH.
929:
860:Pseudomonas aeruginosa
799:. For the phenazonium
763:ortho-phenylenediamine
739:
681:metaaminophenols with
326:n1c3c(nc2c1cccc2)cccc3
953:. 2014. p. 211.
928:
908:biological activities
900:shikimic acid pathway
777:-aminodimethylaniline
737:
61:9,10-Diazaanthracene
46:Preferred IUPAC name
1218:10.1128/JB.02273-12
846:Pantoea agglomerans
489:with the formula (C
419:insoluble in water
414:Solubility in water
18:
930:
869:biological control
849:. These phenazine
740:
683:phthalic anhydride
505:. It is a dibenzo
471:Infobox references
16:
1315:978-3-540-21124-2
1257:(14): 2470–2472.
1154:(38): 9459–9460.
1148:J. Am. Chem. Soc.
1122:978-0-12-027727-8
1032:Collected Volumes
1025:Organic Syntheses
968:978-0-85404-182-4
716:hydrochloric acid
606:naphthophenazines
585:-phenylenediamine
556:pyrolysis of the
550:Wohl–Aue reaction
479:Chemical compound
477:
476:
248:CompTox Dashboard
112:Interactive image
1384:
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1160:10.1021/ja011243
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1058:(6): 1659–1670.
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876:methanophenazine
851:natural products
827:Natural products
712:aqueous solution
710:dissociation in
697:groups into the
614:naphthotolazines
487:organic compound
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455:
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342:Chemical formula
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59:Dibenzopyrazine
52:
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1346:Chisholm, Hugh
1327:
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1314:
1306:10.1007/b96889
1284:
1241:
1212:(7): 1371–80.
1187:
1136:
1121:
1095:
1038:
1010:
1004:978-3527306732
1003:
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967:
937:
936:
934:
931:
904:chorismic acid
895:
892:
828:
825:
809:Benzocinnoline
791:and mordanted
731:
730:Aminophenazine
728:
727:
726:
671:
664:hydroxylgroups
654:. They add on
641:
622:ortho-quinones
618:ortho-diamines
600:
597:
596:
595:
588:
574:
564:
563:of azobenzoate
545:
542:
516:, such as the
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442:standard state
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949:. Cambridge:
948:
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927:
923:
921:
917:
916:saphenic acid
913:
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905:
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889:
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764:
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749:
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736:
729:
725:are produced.
724:
721:
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713:
709:
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696:
692:
688:
684:
680:
676:
672:
669:
665:
661:
657:
656:alkyl iodides
653:
649:
646:
642:
639:
635:
634:azo compounds
631:
627:
623:
619:
615:
611:
607:
603:
602:
598:
593:
592:lead peroxide
589:
586:
584:
579:
575:
573:
569:
566:oxidation of
565:
562:
559:
555:
554:
553:
551:
543:
541:
539:
538:Sulfuric acid
535:
531:
527:
523:
519:
518:toluylene red
515:
511:
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488:
484:
472:
465:
460:
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403:Boiling point
401:
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393:Melting point
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184:ECHA InfoCard
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1319:, retrieved
1297:
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1250:
1244:
1209:
1203:
1190:
1176:cite journal
1151:
1146:
1139:
1104:
1098:
1055:
1051:
1041:
1031:
1023:
1020:"Pyocyanine"
1013:
986:
946:
941:
897:
894:Biosynthesis
884:menaquinones
873:
858:
857:produced by
844:
840:Streptomyces
838:
832:
830:
817:phenanthrene
780:
774:
771:
752:
741:
668:fluorescence
636:with dilute
610:naphthazines
582:
578:pyrocatechin
547:
530:crystallizes
482:
481:
152:ChEMBL119870
71:Identifiers
63:Azophenylene
57:Other names
920:esmeraldins
888:ubiquinones
880:methanogens
834:Pseudomonas
797:neutral red
759:neutral red
755:symmetrical
738:Neutral red
599:Derivatives
430:Flash point
374:Appearance
335:Properties
190:100.001.995
132:CHEBI:36674
1377:Phenazines
1366:Categories
1321:2022-07-03
933:References
843:spp., and
821:anthracene
708:hydrolytic
675:rhodamines
624:or by the
572:lead oxide
526:safranines
365:Molar mass
236:2JHR6K463W
163:ChemSpider
99:3D model (
78:CAS Number
65:acridizine
17:Phenazine
1372:Azin dyes
1350:Phenazine
1271:1433-7851
1072:0175-7598
912:pyocyanin
855:pyocyanin
819:bears to
805:safranine
785:oxidation
723:eurhodols
660:anhydride
626:oxidation
544:Synthesis
522:indulines
514:dyestuffs
507:annulated
483:Phenazine
387:1.25g/cm
50:Phenazine
1279:10941105
1236:23292774
1168:11562236
1090:20352425
748:nigrosin
744:induline
720:phenolic
699:molecule
695:hydroxyl
652:oxidants
630:naphthol
510:pyrazine
424:Hazards
1343::
1227:3624522
1131:3532716
1081:2858273
645:azonium
568:aniline
534:alcohol
464:what is
462: (
383:Density
359:
203:PubChem
88:92-82-0
1337:
1312:
1277:
1269:
1234:
1224:
1166:
1129:
1119:
1088:
1078:
1070:
1001:
965:
837:spp.,
813:isomer
811:is an
803:, see
793:cotton
612:, and
558:barium
524:, and
485:is an
459:verify
456:
319:SMILES
143:ChEMBL
40:Names
1200:(PDF)
801:salts
765:with
704:bases
691:amino
687:salts
679:alkyl
648:bases
638:acids
620:with
580:with
570:with
284:InChI
123:ChEBI
101:JSmol
1310:ISBN
1275:PMID
1267:ISSN
1232:PMID
1182:link
1164:PMID
1127:PMID
1117:ISBN
1086:PMID
1068:ISSN
999:ISBN
963:ISBN
918:and
886:and
789:silk
781:meta
779:and
775:para
753:The
746:and
673:The
561:salt
227:UNII
216:4757
172:4593
1352:".
1302:doi
1259:doi
1222:PMC
1214:doi
1210:195
1156:doi
1152:123
1109:doi
1076:PMC
1060:doi
991:doi
955:doi
693:or
253:EPA
206:CID
1368::
1308:,
1296:,
1273:.
1265:.
1255:39
1253:.
1230:.
1220:.
1208:.
1202:.
1178:}}
1174:{{
1162:.
1125:.
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