273:
180:
893:
446:
35:
1162:
26:
599:
581:
824:
757:
and react with ninhydrin. Also, certain amino acid chains are degraded. Therefore, separate analysis is required for identifying such amino acids that either react differently or do not react with ninhydrin at all. The rest of the amino acids are then quantified colorimetrically after separation by
812:. Release of the carboxyl carbon (via ninhydrin) from amino acids recovered from soil that has been treated with a labeled substrate demonstrates assimilation of that substrate into microbial protein. This approach was successfully used to reveal that some ammonium oxidizing bacteria, also called
852:
present in the minute sweat secretions that gather on the finger's unique ridges transfer to surfaces that are touched. Exposure of the surface to ninhydrin converts the amino acids into visibly colored products and thus reveals the print. The test solutions suffer from poor long-term stability,
876:, which reacts readily with nucleophiles (including water). Whereas for most carbonyl compounds, a carbonyl form is more stable than a product of water addition (hydrate), ninhydrin forms a stable hydrate of the central carbon because of the destabilizing effect of the adjacent carbonyl groups.
741:
extending off it. When that nitrogen is deprotected, a ninhydrin test yields blue. Amino-acid residues are attached with their N-terminus protected, so if the next residue has been successfully coupled onto the chain, the test gives a colorless or yellow result.
904:
Ninhydrin may cause allergic, IgE-mediated rhinitis and asthma. A case has been described in which a 41 year old forensic laboratory worker working with
Ninhydrin developed rhinitis and respiratory difficulty. Her specific IgE levels were found almost doubled.
864:(IND-Zn) can be used prior to ninhydrin. This sequence leads to greater overall reaction of the amino acids, possibly by IND-Zn helping to release them from the surface for the subsequent ninhydrin reaction.
454:
426:
1364:
Marsh, K. L., Sims, G. K. and
Mulvaney, R. L. (2005). "Availability of Urea to Autotrophic Ammonia-Oxidizing Bacteria as Related to the Fate of C- and N-labeled Urea Added to Soil".
662:. Upon reaction with these amines, ninhydrin gets converted into deep blue or purple derivatives, which are called Ruhemann's purple. Ninhydrin is most commonly used to detect
1433:
Janssen-Bouwmeester, Roy; Bremmer, Christiaan; Koomen, Linda; Siem-Gorré, Shermayne; de Puit, Marcel (May 2020). "Positive control tests for fingermark development reagents".
532:
1177:
Kaiser, E.; Colescott, R.L.; Bossinger, C.D.; Cook, P.I. (1970). "Color Test for
Detection of Free Terminal Amino Groups in the Solid-Phase Synthesis of Peptides".
713:
Ninhydrin was discovered in 1910 by the German-English chemist
Siegfried Ruhemann (1859–1943). In the same year, Ruhemann observed ninhydrin's reaction with
1476:
Mangle, Milery
Figuera; Xu, Xioama; de Puit, M. (September 2015). "Performance of 1,2-indanedione and the need for sequential treatment of fingerprints".
612:
773:); treatment with ninhydrin should result in a dramatic purple color if the solution contains this species. In the analysis of a chemical reaction by
1399:
1350:
777:(TLC), the reagent can also be used (usually 0.2% solution in either n-butanol or in ethanol). It will detect, on the TLC plate, virtually all
322:
1246:
Keeling, C. I.; Nelson, D. E. (2001). "Changes in the
Intramolecular Stable Carbon Isotope Ratios with Age of the European Cave Bear (
528:
1566:
887:. The reaction of ninhydrin with secondary amines gives an iminium salt, which is also coloured, generally being yellow–orange.
954:
717:. In 1954, Swedish investigators Oden and von Hofsten proposed that ninhydrin could be used to develop latent fingerprints.
800:
originates from the carboxyl carbon of the amino acid. This reaction has been used to release the carboxyl carbons of bone
117:
989:
607:
287:
619:
1421:
746:
730:
520:
494:
230:
175:
137:
1571:
251:
516:
1311:"A Technique to Recover Tracer as Carboxyl-Carbon and α-Nitrogen from Amino Acids in Soil Hydrolysates"
445:
774:
187:
1076:
1006:
1581:
560:
268:
1561:
1107:
981:
1213:
1576:
1586:
1393:
1344:
837:
468:
438:
552:
1259:
1119:
1049:
919:
548:
239:
47:
536:
157:
8:
873:
813:
702:
93:
83:
1514:
Piirilä P, Estlander T, Hytönen M, Keskinen H, Tupasela O, Tuppurainen M (August 1997).
1263:
1123:
1053:
272:
179:
1458:
1381:
1291:
1275:
1232:
1143:
841:
1537:
1493:
1462:
1450:
1417:
1332:
1283:
1194:
1190:
1135:
985:
575:
1446:
1295:
1527:
1485:
1442:
1385:
1373:
1322:
1267:
1228:
1186:
1147:
1127:
1088:
1057:
1018:
977:
805:
667:
635:
410:
345:
958:
219:
1532:
1515:
1489:
1037:
793:
508:
823:
1167:
U.S. Patent no. 2,715,571 (filed: 27 September 1954; issued: 16 August 1955).
892:
857:
759:
590:
500:
1377:
1327:
1310:
25:
1555:
1363:
1308:
1214:"Stable Carbon Isotope Measurements of the Carboxyl Carbons in Bone Collagen"
861:
512:
399:
168:
1497:
1454:
1336:
1287:
1139:
914:
769:
ion can be tested by ninhydrin by dotting it onto a solid support (such as
726:
1541:
1432:
1271:
1198:
1211:
1092:
1022:
884:
880:
663:
540:
524:
1279:
849:
809:
770:
754:
738:
734:
714:
368:
188:
148:
1061:
1131:
782:
589:
Except where otherwise noted, data are given for materials in their
1416:. Home Office, Scientific Research and Development Branch, London.
801:
766:
34:
568:
116:
750:
698:
694:
690:
683:
679:
655:
504:
389:
206:
1516:"Rhinitis caused by ninhydrin develops into occupational asthma"
1513:
845:
675:
128:
1105:
827:
A stain obtained after a thumbprint is treated with ninhydrin.
486:
296:
InChI=1S/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H
786:
778:
671:
659:
556:
306:
InChI=1/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H
106:
1176:
957:. Bergen County Technical Schools. June 2003. Archived from
256:
1245:
1212:
Keeling, C. I.; Nelson, D. E. & Slessor, K. N. (1999).
856:
To further enhance the ability of ninhydrin, a solution of
817:
482:
1309:
Marsh, K. L., Mulvaney, R. L. and Sims, G. K. (2003).
1108:"Detection of Fingerprints by the Ninhydrin Reaction"
478:
1038:"Siegfried Ruhemann and the Discovery of Ninhydrin"
1004:
872:Ninhydrin exists in equilibrium with the triketone
686:sloughed off in fingerprints react with ninhydrin.
404:250 °C (482 °F; 523 K) (decomposes)
792:Upon reaction with ninhydrin, amino acids undergo
474:
1553:
725:Ninhydrin can be used in Kaiser test to monitor
218:
1509:
1507:
1475:
974:Kirk-Othmer Encyclopedia of Chemical Technology
808:in order to help reconstruct the palaeodiet of
92:
1106:Odén, Svante & von Hofsten, Bengt (1954).
972:Rowe, Walter F. (2015). "Forensic Chemistry".
689:Ninhydrin is a white solid that is soluble in
564:
1081:Journal of the Chemical Society, Transactions
1011:Journal of the Chemical Society, Transactions
749:of proteins. Most of the amino acids, except
1504:
1414:Manual of fingerprint development techniques
1398:: CS1 maint: multiple names: authors list (
1349:: CS1 maint: multiple names: authors list (
1074:
1035:
982:10.1002/0471238961.0615180506091908.a01.pub3
544:
271:
178:
156:
1531:
1326:
836:A ninhydrin solution is commonly used by
238:
822:
937:
935:
765:A solution suspected of containing the
267:
1554:
634:(2,2-dihydroxyindane-1,3-dione) is an
169:
697:. Ninhydrin can be considered as the
299:Key: FEMOMIGRRWSMCU-UHFFFAOYSA-N
136:
1163:"Process of Developing Fingerprints"
971:
932:
899:
883:, the amine must condense to give a
309:Key: FEMOMIGRRWSMCU-UHFFFAOYAM
209:
13:
1233:10.1111/j.1475-4754.1999.tb00857.x
785:and also, after vigorous heating,
14:
1598:
1160:
891:
597:
444:
33:
24:
1469:
1447:10.1016/j.forsciint.2020.110259
1426:
1406:
1357:
1302:
1239:
1205:
737:to the solid support, with the
593:(at 25 °C , 100 kPa).
1567:Reagents for organic chemistry
1435:Forensic Science International
1170:
1154:
1099:
1068:
1029:
998:
965:
947:
804:from ancient bones for stable
733:. The chain is linked via its
1:
1042:Journal of Chemical Education
925:
867:
853:especially if not kept cold.
731:solid phase peptide synthesis
69:2,2-Dihydroxyindane-1,3-dione
1533:10.1183/09031936.97.10081918
1490:10.1016/j.scijus.2015.04.002
1191:10.1016/0003-2697(70)90146-6
1036:West, Robert (1 July 1965).
1007:"Cyclic Di- and Tri-ketones"
1005:Ruhemann, Siegfried (1910).
848:surfaces such as paper. The
831:
820:as a carbon source in soil.
7:
1077:"Triketohydrindene Hydrate"
908:
10:
1603:
879:To generate the ninhydrin
745:Ninhydrin is also used in
708:
1378:10.1007/s00374-005-0004-2
955:"Fingerprinting Analysis"
775:thin layer chromatography
587:
425:
420:
338:
318:
283:
76:
71:1,2,3-Indantrione hydrate
66:
46:
41:
32:
23:
654:. It is used to detect
495:Precautionary statements
1328:10.1093/jaoac/86.6.1106
1179:Analytical Biochemistry
720:
670:cases, as the terminal
330:O=C2c1ccccc1C(=O)C2(O)O
942:Chemicals and reagents
838:forensic investigators
828:
1478:Science & Justice
1272:10.1007/S004420000611
1075:Ruhemann, S. (1910).
826:
1412:Menzel, E.R. (1986)
1093:10.1039/ct9109702025
1023:10.1039/ct9109701438
920:Paper chromatography
747:qualitative analysis
48:Preferred IUPAC name
1264:2001Oecol.127..495K
1124:1954Natur.173..449O
1054:1965JChEd..42..386W
874:indane-1,2,3-trione
842:latent fingerprints
840:in the analysis of
814:nitrifying bacteria
703:indane-1,2,3-trione
411:Solubility in water
376: g·mol
20:
1572:Forensic chemicals
944:, 2008–2010, Merck
829:
796:. The released CO
638:with the formula C
620:Infobox references
18:
1118:(4401): 449–450.
1062:10.1021/ed042p386
976:. pp. 1–19.
900:Effects on health
628:Chemical compound
626:
625:
576:Safety data sheet
469:Hazard statements
252:CompTox Dashboard
118:Interactive image
1594:
1546:
1545:
1535:
1526:(8): 1918–1921.
1511:
1502:
1501:
1473:
1467:
1466:
1430:
1424:
1410:
1404:
1403:
1397:
1389:
1366:Biol. Fert. Soil
1361:
1355:
1354:
1348:
1340:
1330:
1321:(6): 1106–1111.
1306:
1300:
1299:
1243:
1237:
1236:
1218:
1209:
1203:
1202:
1174:
1168:
1166:
1158:
1152:
1151:
1132:10.1038/173449a0
1103:
1097:
1096:
1072:
1066:
1065:
1033:
1027:
1026:
1002:
996:
995:
969:
963:
962:
961:on 13 June 2007.
951:
945:
939:
895:
806:isotope analysis
636:organic compound
610:
604:
601:
600:
570:
566:
562:
558:
554:
550:
546:
542:
538:
534:
530:
526:
522:
518:
514:
510:
506:
502:
488:
484:
480:
476:
448:
375:
346:Chemical formula
276:
275:
260:
258:
242:
222:
211:
190:
182:
171:
160:
140:
120:
96:
37:
28:
21:
17:
1602:
1601:
1597:
1596:
1595:
1593:
1592:
1591:
1582:1,3-Indandiones
1552:
1551:
1550:
1549:
1512:
1505:
1474:
1470:
1431:
1427:
1411:
1407:
1391:
1390:
1362:
1358:
1342:
1341:
1307:
1303:
1244:
1240:
1216:
1210:
1206:
1175:
1171:
1159:
1155:
1104:
1100:
1073:
1069:
1034:
1030:
1003:
999:
992:
970:
966:
953:
952:
948:
940:
933:
928:
911:
902:
870:
834:
799:
794:decarboxylation
723:
711:
653:
649:
645:
641:
629:
622:
617:
616:
615: ?)
606:
602:
598:
594:
497:
471:
457:
441:
413:
373:
362:
358:
354:
348:
334:
331:
326:
325:
314:
311:
310:
307:
301:
300:
297:
291:
290:
279:
261:
254:
245:
225:
212:
200:
163:
143:
123:
110:
99:
86:
72:
70:
62:
61:
52:2,2-Dihydroxy-1
12:
11:
5:
1600:
1590:
1589:
1584:
1579:
1574:
1569:
1564:
1562:Chemical tests
1548:
1547:
1503:
1484:(5): 343–346.
1468:
1425:
1405:
1372:(2): 137–145.
1356:
1301:
1258:(4): 495–500.
1248:Ursus spelaeus
1238:
1204:
1169:
1161:Oden, Svante.
1153:
1098:
1067:
1048:(7): 386–388.
1028:
997:
990:
964:
946:
930:
929:
927:
924:
923:
922:
917:
910:
907:
901:
898:
897:
896:
869:
866:
858:1,2-indandione
833:
830:
797:
760:chromatography
722:
719:
710:
707:
651:
647:
643:
639:
627:
624:
623:
618:
596:
595:
591:standard state
588:
585:
584:
579:
572:
571:
533:P305+P351+P338
498:
493:
490:
489:
472:
467:
464:
463:
458:
453:
450:
449:
442:
437:
434:
433:
423:
422:
418:
417:
414:
409:
406:
405:
402:
396:
395:
392:
386:
385:
382:
378:
377:
371:
365:
364:
360:
356:
352:
349:
344:
341:
340:
336:
335:
333:
332:
329:
321:
320:
319:
316:
315:
313:
312:
308:
305:
304:
302:
298:
295:
294:
286:
285:
284:
281:
280:
278:
277:
264:
262:
250:
247:
246:
244:
243:
235:
233:
227:
226:
224:
223:
215:
213:
205:
202:
201:
199:
198:
194:
192:
184:
183:
173:
165:
164:
162:
161:
153:
151:
145:
144:
142:
141:
133:
131:
125:
124:
122:
121:
113:
111:
104:
101:
100:
98:
97:
89:
87:
82:
79:
78:
74:
73:
68:
64:
63:
51:
50:
44:
43:
39:
38:
30:
29:
9:
6:
4:
3:
2:
1599:
1588:
1585:
1583:
1580:
1578:
1577:Geminal diols
1575:
1573:
1570:
1568:
1565:
1563:
1560:
1559:
1557:
1543:
1539:
1534:
1529:
1525:
1521:
1517:
1510:
1508:
1499:
1495:
1491:
1487:
1483:
1479:
1472:
1464:
1460:
1456:
1452:
1448:
1444:
1440:
1436:
1429:
1423:
1419:
1415:
1409:
1401:
1395:
1387:
1383:
1379:
1375:
1371:
1367:
1360:
1352:
1346:
1338:
1334:
1329:
1324:
1320:
1316:
1312:
1305:
1297:
1293:
1289:
1285:
1281:
1277:
1273:
1269:
1265:
1261:
1257:
1253:
1249:
1242:
1234:
1230:
1226:
1222:
1215:
1208:
1200:
1196:
1192:
1188:
1184:
1180:
1173:
1164:
1157:
1149:
1145:
1141:
1137:
1133:
1129:
1125:
1121:
1117:
1113:
1109:
1102:
1094:
1090:
1087:: 2025–2031.
1086:
1082:
1078:
1071:
1063:
1059:
1055:
1051:
1047:
1043:
1039:
1032:
1024:
1020:
1017:: 1438–1449.
1016:
1012:
1008:
1001:
993:
991:9780471238966
987:
983:
979:
975:
968:
960:
956:
950:
943:
938:
936:
931:
921:
918:
916:
913:
912:
906:
894:
890:
889:
888:
886:
882:
877:
875:
865:
863:
862:zinc chloride
859:
854:
851:
847:
843:
839:
825:
821:
819:
815:
811:
807:
803:
795:
790:
788:
784:
780:
776:
772:
768:
763:
761:
756:
752:
748:
743:
740:
736:
732:
728:
718:
716:
706:
704:
700:
696:
692:
687:
685:
681:
677:
673:
669:
665:
661:
657:
637:
633:
621:
614:
609:
592:
586:
583:
582:External MSDS
580:
577:
574:
573:
499:
496:
492:
491:
473:
470:
466:
465:
462:
459:
456:
452:
451:
447:
443:
440:
436:
435:
431:
429:
424:
419:
415:
412:
408:
407:
403:
401:
400:Melting point
398:
397:
393:
391:
388:
387:
383:
380:
379:
372:
370:
367:
366:
350:
347:
343:
342:
337:
328:
327:
324:
317:
303:
293:
292:
289:
282:
274:
270:
269:DTXSID7025716
266:
265:
263:
253:
249:
248:
241:
237:
236:
234:
232:
229:
228:
221:
217:
216:
214:
208:
204:
203:
196:
195:
193:
191:
186:
185:
181:
177:
174:
172:
170:ECHA InfoCard
167:
166:
159:
155:
154:
152:
150:
147:
146:
139:
138:ChEMBL1221925
135:
134:
132:
130:
127:
126:
119:
115:
114:
112:
108:
103:
102:
95:
91:
90:
88:
85:
81:
80:
75:
65:
59:
56:-indene-1,3(2
55:
49:
45:
40:
36:
31:
27:
22:
16:
1587:Protein dyes
1523:
1520:Eur Respir J
1519:
1481:
1477:
1471:
1438:
1434:
1428:
1413:
1408:
1394:cite journal
1369:
1365:
1359:
1345:cite journal
1318:
1314:
1304:
1255:
1251:
1247:
1241:
1224:
1221:Archaeometry
1220:
1207:
1185:(2): 595–8.
1182:
1178:
1172:
1156:
1115:
1111:
1101:
1084:
1080:
1070:
1045:
1041:
1031:
1014:
1010:
1000:
973:
967:
959:the original
949:
941:
915:Hydrindantin
903:
878:
871:
855:
835:
791:
764:
744:
727:deprotection
724:
712:
688:
678:residues in
664:fingerprints
631:
630:
460:
427:
384:White solid
77:Identifiers
67:Other names
57:
53:
15:
1315:J. AOAC Int
1227:: 151–164.
885:Schiff base
881:chromophore
850:amino acids
715:amino acids
455:Signal word
394:0.862 g/cm
381:Appearance
339:Properties
176:100.006.926
1556:Categories
1441:: 110259.
1422:0862522307
926:References
868:Reactivity
810:cave bears
783:carbamates
771:silica gel
755:hydrolyzed
739:N-terminus
735:C-terminus
439:Pictograms
369:Molar mass
240:HCL6S9K23A
149:ChemSpider
105:3D model (
84:CAS Number
19:Ninhydrin
1463:214732288
1252:Oecologia
832:Forensics
632:Ninhydrin
561:P403+P233
553:P337+P313
549:P332+P313
529:P304+P340
525:P302+P352
521:P301+P312
430:labelling
197:213-340-1
189:EC Number
1498:26385717
1455:32224429
1337:14979690
1296:23508811
1288:28547486
1140:13144778
909:See also
802:collagen
767:ammonium
684:proteins
680:peptides
668:forensic
421:Hazards
94:485-47-2
1542:9272939
1386:6245255
1280:4222957
1260:Bibcode
1199:5443684
1148:4187222
1120:Bibcode
1050:Bibcode
751:proline
709:History
699:hydrate
695:acetone
691:ethanol
656:ammonia
613:what is
611: (
461:Warning
416:20 g L
390:Density
374:178.143
363:
207:PubChem
60:)-dione
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1112:Nature
988:
846:porous
787:amides
779:amines
753:, are
676:lysine
672:amines
660:amines
608:verify
605:
578:(SDS)
323:SMILES
129:ChEMBL
42:Names
1459:S2CID
1382:S2CID
1292:S2CID
1276:JSTOR
1217:(PDF)
1144:S2CID
650:C(OH)
288:InChI
220:10236
107:JSmol
1538:PMID
1494:PMID
1451:PMID
1418:ISBN
1400:link
1351:link
1333:PMID
1284:PMID
1250:)".
1195:PMID
1136:PMID
986:ISBN
860:and
818:urea
816:use
721:Uses
693:and
682:and
658:and
646:(CO)
569:P501
565:P405
557:P362
545:P330
541:P321
537:P312
517:P280
513:P271
509:P270
505:P264
501:P261
487:H335
483:H319
479:H315
475:H302
231:UNII
158:9819
1528:doi
1486:doi
1443:doi
1439:310
1374:doi
1323:doi
1268:doi
1256:127
1229:doi
1187:doi
1128:doi
1116:173
1089:doi
1058:doi
1019:doi
978:doi
844:on
729:in
701:of
674:of
666:in
428:GHS
257:EPA
210:CID
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