77:
67:
47:
372:
259:
739:
729:
734:
834:
830:
37:
1350:
1062:
835:
833:
1825:
Mohrig, Jerry R.; Nienhuis, David M.; Linck, Catherine F.; Van Zoeren, Carol; Fox, Brian G.; Mahaffy, Peter G. (June 1985). "The design of laboratory experiments in the 1980's: A case study on the oxidation of alcohols with household bleach".
1129:. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to
851:
747:
709:
76:
1754:
809:
836:
66:
1880:
Valsamma
Varghese; Manasi Saha; Kenneth M. Nicholas (1989). "Alkylations Using Hexacarbonyl(Propargylium)dicobalt Salts: 2-(1-methyl-2-propynyl)cyclohexanone".
1267:
and then cleaved into phenol and cyclohexanone. Therefore, this newer process without producing the acetone by-product appears attractive and is similar to the
1660:
1564:
966:
2003:"Special Surveillance List of Chemicals, Products, Materials and Equipment Used in the Clandestine Production of Controlled Substances or Listed Chemicals"
1075:
2002:
1366:
In the presence of light, it undergoes alpha-chlorination to give 2-chlorocyclohexanone. It forms a trimethylsilylenol ether upon treatment with
858:
1363:
In addition to the large scale reactions conducted in service of the polymer industry, many reactions have been developed for cyclohexanone.
1758:
421:
46:
1800:
678:
1952:
1722:
651:
1967:
Shulgin, A. T.; MacLean, D. E. (25 September 2008). "Illicit
Synthesis of Phencyclidine (PCP) and Several of Its Analogs".
110:
oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone
1070:
1532:
2030:
386:
1082:
844:
2006:
799:
329:
254:
36:
1942:
1507:
350:
1185:, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of
805:
196:
990:
977:
738:
1674:
1444:
266:
156:
1702:
881:
367:
2025:
1779:
575:
728:
1367:
1331:
627:
1804:
1460:
761:
721:
551:
1627:
1443:
and its analogs and is often subject to purchase restrictions, such as being listed on the
733:
338:
96:
1605:
216:
8:
1320:
1288:
132:
122:
80:
Ball-and-stick model of cyclohexanone viewed side-on, showing the non-planar conformation
371:
258:
176:
1114:
1479:
1984:
1948:
1728:
1718:
1381:
1280:
1256:
1205:
H as an intermediate. In some cases, purified cyclohexanol, obtained by hydration of
1976:
1919:
1910:; I. J. Pachter; M. L. Scheinbaum (1974). "2,2-(Trimethylenedithio)cyclohexanone".
1889:
1862:
1835:
1710:
1587:
1299:
The great majority of cyclohexanone is consumed in the production of precursors to
1122:
1102:
1098:
588:
529:
444:
1714:
1591:
1580:
Viscosity of Pure
Organic Liquids and Binary Liquid Mixtures · Supplement to IV/18
1583:
1284:
894:
318:
1209:, is the precursor. Alternatively, cyclohexanone can be produced by the partial
1907:
1879:
1385:
1287:). An alternative method utilizes the safer and more readily available oxidant
1268:
1053:
1032:
1028:
564:
1980:
1560:
1503:
954:
936:
918:
2019:
1923:
1893:
1866:
1652:
1623:
1440:
1324:
1264:
1210:
1190:
518:
508:
247:
1732:
1271:
as a hydroperoxide is formed and then decomposed to yield two key products.
775:
1906:
1456:
1178:
1126:
1044:
613:
1245:
This process can also be adjusted to favor the formation of cyclohexanol.
857:
1988:
1938:
1853:
M. S. Newman; M. D. Farbman; H. Hipsher (1945). "2-chlorocyclohexanone".
1374:
1335:
1316:
1308:
1206:
1186:
1142:
870:
19:
843:
236:
1252:
1248:
1182:
850:
540:
486:
463:
267:
207:
1839:
1312:
1300:
607:
1578:
Ch. Wohlfarth. "Viscosity of cyclohexanone". In M.D. Lechner (ed.).
1459:, cyclohexanone is not carcinogenic and is moderately toxic, with a
1349:
1052:
Except where otherwise noted, data are given for materials in their
70:
Skeletal formula viewed side-on, showing the non-planar conformation
1852:
1327:
1260:
816:
293:
227:
1558:
1279:
Cyclohexanone can be prepared from cyclohexanol by oxidation with
155:
1678:
1537:
1339:
1304:
498:
490:
305:
1944:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
1315:. For this application, the KA oil (see above) is oxidized with
1214:
1118:
1022:
187:
1504:"CDC – NIOSH Pocket Guide to Chemical Hazards – Cyclohexanone"
1936:
1824:
1657:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
1319:. The other half of the cyclohexanone supply is converted to
1130:
1125:. This colorless oily liquid has a sweet odor reminiscent of
925:
1200 mg/kg (cat, orally); 2362 mg/kg (rat, orally)
167:
145:
1947:(6th ed.), New York: Wiley-Interscience, p. 1736,
355:
1709:. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KgaA.
1003:
481:
284:
779:
1439:
Cyclohexanone has been used in the illicit production of
767:
787:
1661:
National
Institute for Occupational Safety and Health
1565:
National
Institute for Occupational Safety and Health
1307:. About half of the world's supply is converted to
783:
1772:
771:
1780:"Phenol – The essential chemical industry online"
2017:
791:
317:
832:
523:155.65 °C (312.17 °F; 428.80 K)
131:
1966:
1707:Ullmann's Encyclopedia of Industrial Chemistry
1639:Cyclohexanone: toxicity for animals and humans
1141:Cyclohexanone is produced by the oxidation of
1463:of 25 ppm for the vapor. It is an irritant.
1801:"Oxidation of Cyclohexanol to Cyclohexanone"
1598:
1571:
1757:. American Chemical Society. Archived from
1746:
1696:
1694:
1692:
1690:
1688:
1508:Centers for Disease Control and Prevention
1189:. The oxidation involves radicals and the
1145:in air, typically using cobalt catalysts:
370:
257:
215:
1577:
1527:
1525:
337:
1559:NIOSH Pocket Guide to Chemical Hazards.
1251:developed a process in which benzene is
1113:CO. The molecule consists of six-carbon
1752:
1701:Musser, Michael T. (October 15, 2011).
1685:
1619:
1617:
1615:
395:InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
366:
235:
2018:
1700:
1647:
1645:
1554:
1552:
1550:
1548:
1522:
889:420 °C (788 °F; 693 K)
513:−47 °C (−53 °F; 226 K)
405:InChI=1/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
248:
1274:
875:44 °C (111 °F; 317 K)
398:Key: JHIVVAPYMSGYDF-UHFFFAOYSA-N
195:
175:
50:Ball-and-stick model of cyclohexanone
1612:
535:8.6 g/100 mL (20 °C)
1995:
1642:
1545:
1388:gives the oximinecarboxylic ester:
961:4706 ppm (mouse, 1.5 hr)
408:Key: JHIVVAPYMSGYDF-UHFFFAOYAY
308:
292:
13:
1755:"What's New in Phenol Production?"
1753:Plotkin, Jeffrey S. (2016-03-21).
1358:
828:
75:
65:
45:
35:
14:
2042:
997:TWA 25 ppm (100 mg/m)
40:Skeletal formula of cyclohexanone
1703:"Cyclohexanol and Cyclohexanone"
1348:
1060:
737:
732:
727:
1960:
1930:
1900:
1873:
1846:
1818:
1793:
1667:
1056:(at 25 °C , 100 kPa).
943:8000 ppm (rat, 4 hr)
1633:
1496:
1472:
1434:
468:98.15 g/mol
1:
1828:Journal of Chemical Education
1715:10.1002/14356007.a08_217.pub2
1592:10.1007/978-3-540-75486-2_192
1466:
1136:
971:(US health exposure limits):
1311:, one of two precursors for
7:
1480:"ICSC 0425 – CYCLOHEXANONE"
1409:OH + NOCl → HON=CH(CH
1370:in the presence of base.
907:or concentration (LD, LC):
61:
31:
10:
2047:
1675:"Cyclohexanone (CID 7967)"
1533:"Cyclohexanone (CID 7967)"
17:
1981:10.3109/15563657608988157
1450:
1445:Special Surveillance List
1373:It forms an enamine with
1259:. This latter product is
1050:
1014:
965:
903:
708:
703:
620:
569:5 mmHg (20 °C)
503:0.9478 g/mL, liquid
437:
417:
382:
115:
107:
95:
90:
60:
30:
2031:IARC Group 3 carcinogens
1924:10.15227/orgsyn.054.0039
1894:10.15227/orgsyn.067.0141
1867:10.15227/orgsyn.025.0022
800:Precautionary statements
543:in all organic solvents
18:Not to be confused with
1294:
576:Magnetic susceptibility
1368:trimethylsilylchloride
1323:. In the presence of
984:TWA 50 ppm (200 mg/m)
839:
582:−62.04·10 cm/mol
81:
71:
51:
41:
838:
645:+229.03 J·K·mol
79:
69:
49:
39:
937:median concentration
821:(fire diamond)
699:−3519.3 kJ·mol
97:Preferred IUPAC name
1969:Clinical Toxicology
1937:Smith, Michael B.;
1321:cyclohexanone oxime
1289:sodium hypochlorite
1177:This process forms
672:−270.7 kJ·mol
530:Solubility in water
27:
2009:on April 20, 2011.
1275:Laboratory methods
1083:Infobox references
1015:Related compounds
1006:(Immediate danger)
840:
82:
72:
52:
42:
25:
1954:978-0-471-72091-1
1840:10.1021/ed062p519
1724:978-3-527-30673-2
1624:Sigma-Aldrich Co.
1382:nitrosyl chloride
1338:, a precursor to
1281:chromium trioxide
1257:cyclohexylbenzene
1091:Chemical compound
1089:
1088:
1040:Related compounds
762:Hazard statements
476:Colorless liquid
351:CompTox Dashboard
157:Interactive image
86:
85:
56:
55:
2038:
2011:
2010:
2005:. Archived from
1999:
1993:
1992:
1964:
1958:
1957:
1934:
1928:
1927:
1904:
1898:
1897:
1877:
1871:
1870:
1850:
1844:
1843:
1822:
1816:
1815:
1813:
1812:
1803:. Archived from
1797:
1791:
1790:
1788:
1787:
1776:
1770:
1769:
1767:
1766:
1750:
1744:
1743:
1741:
1739:
1698:
1683:
1682:
1671:
1665:
1664:
1649:
1640:
1637:
1631:
1621:
1610:
1609:
1608:. Sigma-Aldrich.
1602:
1596:
1595:
1575:
1569:
1568:
1556:
1543:
1542:
1529:
1520:
1519:
1517:
1515:
1500:
1494:
1493:
1491:
1490:
1476:
1430:
1352:
1099:organic compound
1073:
1067:
1064:
1063:
955:lowest published
895:Explosive limits
860:
853:
846:
831:
811:
807:
793:
789:
785:
781:
777:
773:
769:
741:
736:
731:
695:
668:
641:
621:Thermochemistry
589:Refractive index
445:Chemical formula
375:
374:
359:
357:
341:
321:
310:
296:
269:
261:
250:
239:
219:
199:
179:
159:
135:
62:
32:
28:
24:
2046:
2045:
2041:
2040:
2039:
2037:
2036:
2035:
2016:
2015:
2014:
2001:
2000:
1996:
1965:
1961:
1955:
1935:
1931:
1905:
1901:
1878:
1874:
1851:
1847:
1823:
1819:
1810:
1808:
1799:
1798:
1794:
1785:
1783:
1778:
1777:
1773:
1764:
1762:
1751:
1747:
1737:
1735:
1725:
1699:
1686:
1673:
1672:
1668:
1653:"Cyclohexanone"
1651:
1650:
1643:
1638:
1634:
1622:
1613:
1606:"Cyclohexanone"
1604:
1603:
1599:
1584:Springer-Verlag
1576:
1572:
1557:
1546:
1531:
1530:
1523:
1513:
1511:
1502:
1501:
1497:
1488:
1486:
1478:
1477:
1473:
1469:
1453:
1437:
1428:
1424:
1420:
1416:
1412:
1408:
1404:
1400:
1396:
1392:
1384:and ethanol in
1380:Treatment with
1361:
1359:Other reactions
1297:
1285:Jones oxidation
1277:
1240:
1236:
1232:
1228:
1224:
1204:
1200:
1196:
1172:
1168:
1164:
1160:
1156:
1152:
1139:
1115:cyclic molecule
1112:
1108:
1092:
1085:
1080:
1079:
1078: ?)
1069:
1065:
1061:
1057:
1041:
1025:
1007:
994:
981:
958:
952:
940:
934:
922:
916:
886:
883:
865:
864:
863:
862:
855:
848:
841:
837:
829:
802:
764:
750:
724:
696:
693:
687:
683:
680:
679:Std enthalpy of
669:
666:
660:
656:
653:
652:Std enthalpy of
642:
639:
632:
629:
599:
597:
579:
532:
457:
453:
447:
433:
430:
425:
424:
413:
410:
409:
406:
400:
399:
396:
390:
389:
378:
360:
353:
344:
324:
311:
299:
279:
242:
222:
202:
182:
162:
149:
138:
125:
111:
103:
102:
23:
12:
11:
5:
2044:
2034:
2033:
2028:
2026:Cycloalkanones
2013:
2012:
1994:
1975:(4): 553–560.
1959:
1953:
1929:
1908:R. B. Woodward
1899:
1872:
1845:
1817:
1792:
1771:
1745:
1723:
1684:
1666:
1641:
1632:
1611:
1597:
1570:
1544:
1521:
1495:
1470:
1468:
1465:
1452:
1449:
1436:
1433:
1432:
1431:
1426:
1422:
1418:
1414:
1410:
1406:
1402:
1398:
1394:
1386:sulfur dioxide
1360:
1357:
1356:
1355:
1354:
1353:
1296:
1293:
1276:
1273:
1269:cumene process
1253:hydroalkylated
1243:
1242:
1238:
1234:
1230:
1226:
1222:
1202:
1198:
1194:
1175:
1174:
1170:
1166:
1162:
1158:
1154:
1150:
1138:
1135:
1110:
1106:
1090:
1087:
1086:
1081:
1059:
1058:
1054:standard state
1051:
1048:
1047:
1042:
1039:
1036:
1035:
1033:cycloheptanone
1029:Cyclopentanone
1026:
1020:
1017:
1016:
1012:
1011:
1008:
1002:
999:
998:
995:
989:
986:
985:
982:
976:
973:
972:
963:
962:
959:
950:
948:
945:
944:
941:
932:
930:
927:
926:
923:
914:
912:
909:
908:
901:
900:
897:
891:
890:
887:
880:
877:
876:
873:
867:
866:
856:
849:
842:
827:
826:
825:
824:
822:
813:
812:
810:P305+P351+P338
803:
798:
795:
794:
765:
760:
757:
756:
751:
746:
743:
742:
725:
720:
717:
716:
706:
705:
701:
700:
697:
691:
685:
677:
674:
673:
670:
664:
658:
650:
647:
646:
643:
637:
626:
623:
622:
618:
617:
616:at 25 °C
610:
604:
603:
600:
595:
587:
584:
583:
580:
574:
571:
570:
567:
565:Vapor pressure
561:
560:
557:
548:
547:
544:
537:
536:
533:
528:
525:
524:
521:
515:
514:
511:
505:
504:
501:
495:
494:
484:
478:
477:
474:
470:
469:
466:
460:
459:
455:
451:
448:
443:
440:
439:
435:
434:
432:
431:
428:
420:
419:
418:
415:
414:
412:
411:
407:
404:
403:
401:
397:
394:
393:
385:
384:
383:
380:
379:
377:
376:
363:
361:
349:
346:
345:
343:
342:
334:
332:
326:
325:
323:
322:
314:
312:
304:
301:
300:
298:
297:
289:
287:
281:
280:
278:
277:
273:
271:
263:
262:
252:
244:
243:
241:
240:
232:
230:
224:
223:
221:
220:
212:
210:
204:
203:
201:
200:
192:
190:
184:
183:
181:
180:
172:
170:
164:
163:
161:
160:
152:
150:
143:
140:
139:
137:
136:
128:
126:
121:
118:
117:
113:
112:
109:
105:
104:
100:
99:
93:
92:
88:
87:
84:
83:
73:
58:
57:
54:
53:
43:
26:Cyclohexanone
9:
6:
4:
3:
2:
2043:
2032:
2029:
2027:
2024:
2023:
2021:
2008:
2004:
1998:
1990:
1986:
1982:
1978:
1974:
1970:
1963:
1956:
1950:
1946:
1945:
1940:
1933:
1925:
1921:
1917:
1913:
1909:
1903:
1895:
1891:
1887:
1883:
1876:
1868:
1864:
1860:
1856:
1849:
1841:
1837:
1833:
1829:
1821:
1807:on 2012-04-26
1806:
1802:
1796:
1781:
1775:
1761:on 2019-10-27
1760:
1756:
1749:
1734:
1730:
1726:
1720:
1716:
1712:
1708:
1704:
1697:
1695:
1693:
1691:
1689:
1680:
1676:
1670:
1662:
1658:
1654:
1648:
1646:
1636:
1629:
1628:Cyclohexanone
1625:
1620:
1618:
1616:
1607:
1601:
1593:
1589:
1585:
1581:
1574:
1566:
1562:
1555:
1553:
1551:
1549:
1540:
1539:
1534:
1528:
1526:
1509:
1505:
1499:
1485:
1481:
1475:
1471:
1464:
1462:
1458:
1448:
1446:
1442:
1441:phencyclidine
1391:
1390:
1389:
1387:
1383:
1378:
1376:
1371:
1369:
1364:
1351:
1347:
1346:
1345:
1344:
1343:
1341:
1337:
1333:
1329:
1326:
1325:sulfuric acid
1322:
1318:
1314:
1310:
1306:
1302:
1292:
1290:
1286:
1282:
1272:
1270:
1266:
1265:hydroperoxide
1262:
1258:
1254:
1250:
1246:
1220:
1219:
1218:
1216:
1212:
1211:hydrogenation
1208:
1192:
1191:hydroperoxide
1188:
1184:
1180:
1148:
1147:
1146:
1144:
1134:
1132:
1128:
1124:
1120:
1116:
1104:
1100:
1096:
1095:Cyclohexanone
1084:
1077:
1072:
1055:
1049:
1046:
1043:
1038:
1037:
1034:
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993:(Recommended)
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101:Cyclohexanone
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2007:the original
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1939:March, Jerry
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1827:
1820:
1809:. Retrieved
1805:the original
1795:
1784:. Retrieved
1782:. 2017-01-11
1774:
1763:. Retrieved
1759:the original
1748:
1736:. Retrieved
1706:
1669:
1656:
1635:
1600:
1579:
1573:
1536:
1512:. Retrieved
1498:
1487:. Retrieved
1483:
1474:
1457:cyclohexanol
1454:
1438:
1379:
1372:
1365:
1362:
1330:, the oxime
1298:
1278:
1247:
1244:
1179:cyclohexanol
1176:
1140:
1127:benzaldehyde
1094:
1093:
1045:Cyclohexanol
967:
904:
882:Autoignition
817:
753:
710:
688:
661:
634:
592:
553:
429:C1CCC(=O)CC1
116:Identifiers
108:Other names
15:
1738:January 27,
1447:in the US.
1435:Illicit use
1375:pyrrolidine
1336:caprolactam
1317:nitric acid
1309:adipic acid
1207:cyclohexene
1187:adipic acid
1143:cyclohexane
1121:functional
919:median dose
905:Lethal dose
884:temperature
871:Flash point
748:Signal word
473:Appearance
438:Properties
255:100.003.302
197:ChEMBL18850
177:CHEBI:17854
20:Cyclexanone
2020:Categories
1912:Org. Synth
1882:Org. Synth
1855:Org. Synth
1834:(6): 519.
1811:2012-07-09
1786:2019-10-27
1765:2019-10-27
1514:August 24,
1489:2022-08-24
1484:inchem.org
1467:References
1332:rearranges
1249:ExxonMobil
1183:by-product
1137:Production
722:Pictograms
681:combustion
612:2.02
541:Solubility
487:Peppermint
464:Molar mass
339:5QOR3YM052
208:ChemSpider
144:3D model (
123:CAS Number
1313:nylon 6,6
1301:Nylon 6,6
1169:CO + H
1101:with the
899:1.1–9.4%
713:labelling
654:formation
628:Std molar
608:Viscosity
546:Miscible
276:203-631-1
268:EC Number
1941:(2007),
1733:46878292
1663:(NIOSH).
1567:(NIOSH).
1401:CO + C
1328:catalyst
1261:oxidized
1229:OH + 2 H
1021:Related
1010:700 ppm
818:NFPA 704
704:Hazards
578:(χ)
458:O
228:DrugBank
133:108-94-1
1888:: 141.
1679:PubChem
1561:"#0166"
1538:PubChem
1340:nylon 6
1305:Nylon 6
1161:→ (CH
1117:with a
1103:formula
1097:is the
1076:what is
1074: (
1023:ketones
630:entropy
499:Density
491:acetone
306:PubChem
237:DB02060
1989:975751
1987:
1951:
1918:: 39.
1861:: 22.
1731:
1721:
1451:Safety
1429:+ HCl
1215:phenol
1119:ketone
1071:verify
1068:
754:Danger
602:1.447
493:-like
422:SMILES
294:C00414
188:ChEMBL
91:Names
1510:(CDC)
1455:Like
1263:to a
1233:→ (CH
1181:as a
1131:nylon
1123:group
968:NIOSH
559:0.81
387:InChI
168:ChEBI
146:JSmol
1985:PMID
1949:ISBN
1740:2009
1729:OCLC
1719:ISBN
1516:2022
1303:and
1295:Uses
1157:+ O
1004:IDLH
806:P280
792:H332
788:H318
784:H315
780:H312
776:H305
772:H302
768:H226
552:log
482:Odor
330:UNII
319:7967
285:KEGG
217:7679
1977:doi
1920:doi
1890:doi
1863:doi
1836:doi
1711:doi
1588:doi
1461:TLV
1393:(CH
1334:to
1255:to
1213:of
1105:(CH
991:REL
978:PEL
711:GHS
692:298
665:298
638:298
489:or
356:EPA
309:CID
2022::
1983:.
1971:.
1916:54
1914:.
1886:67
1884:.
1859:25
1857:.
1832:62
1830:.
1727:.
1717:.
1705:.
1687:^
1677:.
1659:.
1655:.
1644:^
1630:.
1626:,
1614:^
1586:.
1582:.
1563:.
1547:^
1535:.
1524:^
1506:.
1482:.
1417:CO
1377:.
1342::
1291:.
1241:CO
1217::
1199:11
1155:12
1133:.
1031:,
951:Lo
949:LC
933:50
931:LC
915:50
913:LD
808:,
790:,
786:,
782:,
778:,
774:,
770:,
715::
684:(Δ
657:(Δ
614:cP
456:10
1991:.
1979::
1973:9
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1492:.
1427:5
1425:H
1423:2
1421:C
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1415:4
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1411:2
1407:5
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1403:2
1399:5
1397:)
1395:2
1283:(
1239:5
1237:)
1235:2
1231:2
1227:5
1225:H
1223:6
1221:C
1203:2
1201:O
1197:H
1195:6
1193:C
1173:O
1171:2
1167:5
1165:)
1163:2
1159:2
1153:H
1151:6
1149:C
1111:5
1109:)
1107:2
1066:Y
957:)
953:(
939:)
935:(
921:)
917:(
859:0
852:2
845:1
694:)
689:H
686:c
667:)
662:H
659:f
640:)
635:S
633:(
598:)
596:D
593:n
591:(
554:P
454:H
452:6
450:C
358:)
354:(
148:)
22:.
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