277:
202:
48:
39:
579:: "I was occupied initially with the investigation of the volatile components of excrement in acidic solution. One obtained thereby volatile fatty acids; acetic acid; normal and isobutyric acid; as well as the aromatic substances: phenol, indole and a new substance which is related to indole and which I will name 'skatole'." - Brieger (1878), page 130
453:
570:
Ich habe mich zuerst mit der
Untersuchung der flüchtigen Bestandtheile der Excremente aus sauerer Lösung beschäftigt. Es wurden dabei die flüchtigen Fettsäuren: Essigsäure, normale und Isobuttersäure, sowie die aromatischen Substanzen: Phenol, Indol und eine neue dem Indol verwandte Substanz, die
790:
Oswald, Iain W. H.; Paryani, Twinkle R.; Sosa, Manuel E.; Ojeda, Marcos A.; Altenbernd, Mark R.; Grandy, Jonathan J.; Shafer, Nathan S.; Ngo, Kim; Peat, Jack R.; Melshenker, Bradley G.; Skelly, Ian; Koby, Kevin A.; Page, Michael F. Z.; Martin, Thomas J. (2023-10-12).
1072:, vol. 236, pages 126-151; for Fischer's synthesis of skatole, see page 137. (Fischer was not the first to prepare skatole. It was prepared, via other methods, in 1880 by von Baeyer, and in 1883 by Otto Fischer and German and by Fileti.)
644:, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait for these bees for study. It is also known for being an attractant for the Tasmanian grass grub beetle (
466:
1234:
626:, the scent produced by the resultant concentrations of skatole and indole relative to other substances in the freshener is thus "in-phase" and perceived as pleasant.
326:
1183:
Beechler, J W., J G Miller, and M S Mulla (1994). "Field evaluation of synthetic compounds mediating oviposition in Culex mosquitoes (Diptera: Culicidae)".
1156:
969:"Catabolic pathway for the production of skatole and indoleacetic acid by the acetogen Clostridium drakei, Clostridium scatologenes, and swine manure"
664:(CSO), as streams and lakes containing CSO water have untreated human and industrial waste. CSO sites are thus of particular interest when studying
622:, can be neutralized by combining it with other scents, by producing perfumes or air fresheners that lack skatole and indole. In a manner similar to
702:
enzymes in the lungs. These enzymes convert skatole to a reactive intermediate, 3-methyleneindolenine, which damages cells by forming protein
1083:
291:
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1465:
234:
1404:
623:
255:
473:
661:
605:
139:
197:
1455:
1154:
Osborne, G. O.; Penman, D. R.; Chapman, R. B. (1975). "Attraction of
Aphodius tasmaniae Hope to skatole".
665:
612:
1228:
646:
132:
1315:
1265:
1192:
980:
545:
66:
660:
in both field and laboratory conditions. Because this compound is present in feces, it is found in
533:
272:
98:
1065:
851:
1216:
1136:
930:
1026:"Microbial metabolites of tryptophan in the intestinal tract with special reference to skatole"
1424:
1385:
1334:
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1208:
1128:
1047:
1006:
889:
832:
814:
594:
1101:
Schiestl, F.P. & Roubik, D.W. (2004). "Odor
Compound Detection in Male Euglossine Bees".
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108:
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1001:
968:
793:"Minor, Nonterpenoid Volatile Compounds Drive the Aroma Differences of Exotic Cannabis"
765:
760:
754:
749:
561:
553:
521:
444:
159:
1420:
1286:
1249:
680:
Skatole occurs naturally in the feces of all species of mammals and birds, and in the
654:
1449:
917:
Das Skatol ... (von το σχατος = faeces) ... (Skatole ... (from το σχατος = feces....)
598:
517:
505:
420:
410:
190:
1220:
640:
Skatole is one of many compounds that are attractive to males of various species of
47:
1140:
714:
1277:
694:
in goats, sheep, rats, and some strains of mice. It appears to selectively target
223:
38:
1354:"Nutritional Influences on Skatole Formation and Skatole Metabolism in the Pig"
1309:
Miller, M; Kottler, S; Ramos-Vara, J; Johnson, P; Ganjam, V; Evans, T (2003).
1123:
1114:
967:
Whitehead, T. R.; Price, N. P.; Drake, H. L.; Cotta, M. A. (25 January 2008).
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867:
770:
725:
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379:
170:
17:
905:
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737:
707:
695:
1428:
1389:
1338:
1212:
1132:
1010:
836:
504:
of mammals and birds and is the primary contributor to fecal odor. In low
405:
Fecal Matter (In low concentrations it can have a pleasant flowery aroma)
1295:
1051:
992:
657:
635:
560:, meaning feces. Skatole was discovered in 1877 by the German physician
1329:
1310:
1370:
1204:
549:
528:
524:
210:
1169:
1311:"3-Methylindole Induces Transient Olfactory Mucosal Injury in Ponies"
703:
681:
619:
513:
509:
497:
443:
Except where otherwise noted, data are given for materials in their
684:
501:
150:
138:
131:
121:
400:
890:"Über die flüchtigen Bestandtheile der menschlichen Excremente"
852:"Über die flüchtigen Bestandtheile der menschlichen Excremente"
593:
in the digestive tract of mammals. Tryptophan is converted to
260:
46:
37:
1405:"To Beat Bad Breath, Keep the Bacteria in Your Mouth Happy"
1248:
Yokoyama, M. T.; Carlson, J. R.; Holdeman, L. V. (1977).
854:[On the volatile components of human excrement].
415:
93 to 95 °C (199 to 203 °F; 366 to 368 K)
1084:"Technology; Making Bad Smell Good by Tricking the Nose"
461:
1250:"Isolation and characteristics of a skatole-producing
736:
Skatole is the starting material in the synthesis of
300:
InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3
717:, skatole is regarded as a principal determinant of
310:
InChI=1/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3
222:
585:Biosynthesis, chemical synthesis, and reactions
107:
935:Berichte der Deutschen Chemischen Gesellschaft
856:Berichte der Deutschen Chemischen Gesellschaft
653:Skatole has been shown to be an attractant to
8:
1233:: CS1 maint: multiple names: authors list (
611:It gives a violet color upon treatment with
1157:Australian Journal of Agricultural Research
1030:The American Journal of Clinical Nutrition
275:
200:
178:
26:
1379:
1369:
1328:
1285:
1122:
1041:
1000:
826:
808:
537:. It has also been identified in certain
242:
1024:Yokoyama, M. T.; Carlson, J. R. (1979).
782:
589:Skatole is derived from the amino acid
556:. Its name derives from the Greek root
331:
296:
271:
1258:Applied and Environmental Microbiology
1226:
973:Applied and Environmental Microbiology
618:Skatole, along with the fecal odorant
425:265 °C (509 °F; 538 K)
191:
303:Key: ZFRKQXVRDFCRJG-UHFFFAOYSA-N
158:
7:
604:Skatole can be synthesized via the
571:ich Skatol nennen werde, erhalten."
500:family. It occurs naturally in the
313:Key: ZFRKQXVRDFCRJG-UHFFFAOYAZ
213:
25:
1421:10.1038/scientificamerican0513-30
1403:Franklin, Deborah (1 May 2013).
690:Skatole has been shown to cause
451:
372:
366:
1352:Wesoly, R.; Weiler, U. (2012).
1068:(Indole from phenylhydrazine),
447:(at 25 °C , 100 kPa).
1082:Holusha, John (15 July 1990).
698:, which are the major site of
544:It is used as a fragrance and
512:smell and is found in several
360:
1:
1278:10.1128/AEM.34.6.837-842.1977
894:Journal für Praktische Chemie
713:With the testicular steroid
1103:Journal of Chemical Ecology
1066:"Indole aus Phenylhydrazin"
624:noise-cancelling headphones
33:
1482:
1254:sp. from the bovine rumen"
633:
601:to give the methylindole.
947:10.1002/cber.187901202206
868:10.1002/cber.187701001288
662:combined sewage overflows
441:
347:
322:
287:
91:
86:4-Methyl-2,3-benzopyrrole
81:
65:
60:
32:
929:Brieger, Ludwig (1879).
906:10.1002/prac.18780170111
888:Brieger, Ludwig (1878).
850:Brieger, Ludwig (1877).
810:10.1021/acsomega.3c04496
606:Fischer indole synthesis
395:White crystalline solid
1461:Foul-smelling chemicals
1115:10.1023/A:1021932131526
724:Skatole contributes to
666:mosquito-borne diseases
933:[On skatole].
613:potassium ferrocyanide
582:
51:
42:
1043:10.1093/ajcn/32.1.173
566:
520:, including those of
50:
41:
1316:Veterinary Pathology
1064:Emil Fischer (1886)
993:10.1128/AEM.02458-07
67:Preferred IUPAC name
1466:Perfume ingredients
1409:Scientific American
1330:10.1354/vp.40-4-363
1270:1977ApEnM..34..837Y
1197:1994JCEco..20..281B
985:2008ApEnM..74.1950W
803:(42): 39203–39216.
534:Ziziphus mauritiana
432:Solubility in water
387: g·mol
29:
1371:10.3390/ani2020221
1205:10.1007/BF02064436
1124:20.500.11850/57276
1088:The New York Times
1070:Annalen der Chemie
647:Aphodius tasmaniae
474:Infobox references
52:
43:
27:
1170:10.1071/AR9750839
630:Insect attractant
595:indoleacetic acid
496:belonging to the
482:Chemical compound
480:
479:
256:CompTox Dashboard
140:Interactive image
133:Interactive image
56:
55:
16:(Redirected from
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1021:
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941:(2): 1985–1988.
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494:organic compound
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700:cytochrome P450
692:pulmonary edema
678:
670:West Nile virus
638:
632:
587:
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469: ?)
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339:c1cccc2c1c(c2)C
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5:
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1441:
1395:
1364:(2): 221–242.
1344:
1301:
1264:(6): 837–842.
1240:
1191:(2): 281–291.
1175:
1164:(5): 839–841.
1146:
1109:(1): 253–257.
1093:
1074:
1057:
1036:(1): 173–178.
1016:
959:
921:
880:
842:
781:
780:
778:
775:
774:
773:
768:
766:7-Methylindole
763:
761:5-Methylindole
758:
755:2-Methylindole
752:
750:1-Methylindole
745:
742:
733:
730:
677:
676:Animal studies
674:
631:
628:
599:decarboxylates
586:
583:
562:Ludwig Brieger
554:aroma compound
518:essential oils
506:concentrations
490:3-methylindole
481:
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445:standard state
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84:3-Methylindole
83:
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63:
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24:
18:3-methylindole
14:
13:
10:
9:
6:
4:
3:
2:
1478:
1467:
1464:
1462:
1459:
1457:
1456:Methylindoles
1454:
1453:
1451:
1430:
1426:
1422:
1418:
1415:(5): 30, 32.
1414:
1410:
1406:
1399:
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1387:
1382:
1377:
1372:
1367:
1363:
1359:
1355:
1348:
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1340:
1336:
1331:
1326:
1323:(4): 363–70.
1322:
1318:
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1312:
1305:
1302:
1297:
1293:
1288:
1283:
1279:
1275:
1271:
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1259:
1255:
1253:
1252:Lactobacillus
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979:(6): 1950–3.
978:
974:
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960:
948:
944:
940:
936:
932:
931:"Über Skatol"
925:
922:
918:
907:
903:
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895:
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884:
881:
869:
865:
862:: 1027–1032.
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757:(methylketol)
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584:
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564:(1849–1919).
563:
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421:Boiling point
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411:Melting point
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334:Cc1cc2ccccc12
332:
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273:DTXSID8021775
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192:ECHA InfoCard
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1432:. Retrieved
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1229:cite journal
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950:. Retrieved
938:
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909:. Retrieved
897:
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883:
871:. Retrieved
859:
855:
845:
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796:
785:
735:
723:
715:androstenone
712:
689:
679:
652:
645:
639:
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610:
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588:
576:
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569:
568:Original: "
567:
557:
543:
532:
489:
485:
484:
92:Identifiers
82:Other names
72:
1185:J Chem Ecol
900:: 124–138.
732:Application
642:orchid bees
577:Translation
541:varieties.
508:, it has a
392:Appearance
348:Properties
198:100.001.338
1450:Categories
1434:3 November
952:3 November
911:3 November
873:3 November
777:References
771:Cadaverine
726:bad breath
719:boar taint
696:club cells
658:mosquitoes
634:See also:
591:tryptophan
552:and as an
437:Insoluble
380:Molar mass
244:9W945B5H7R
171:ChemSpider
160:CHEBI:9171
120:3D model (
99:CAS Number
71:3-Methyl-1
819:2470-1343
797:ACS Omega
738:atiprosin
708:fog fever
1429:23627212
1390:26486918
1339:12824507
1221:23784247
1213:24242053
1133:12647866
1011:18223109
837:37901519
828:10601067
744:See also
668:such as
636:Aphodius
597:, which
550:perfumes
548:in many
546:fixative
539:cannabis
525:blossoms
28:Skatole
1381:4494329
1358:Animals
1266:Bibcode
1193:Bibcode
1141:2845587
1002:2268313
981:Bibcode
704:adducts
529:jasmine
514:flowers
510:flowery
486:Skatole
467:what is
465: (
385:131.178
211:PubChem
109:83-34-1
75:-indole
1427:
1388:
1378:
1337:
1296:563703
1294:
1287:242757
1284:
1219:
1211:
1139:
1131:
1052:367144
1050:
1009:
999:
835:
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