283:
188:
33:
24:
493:
756:. Some bacteria with these abilities have specific enzymes involved in the degradation of phthalic acid esters such as phthalate oxygenase, phthalate dioxygenase, phthalate dehydrogenase and phthalate decarboxylase. The developed intermediates of the transesterification or demethylation, ethyl methyl phthalate and dimethyl phthalate, enhance the toxic effect and are able to disrupt the membrane of microorganisms.
709:
639:
498:
497:
747:
of the two diethyl chains of the phthalate to produce monoethyl phthalate, followed by phthalic acid. This reaction occurs very slowly in an abiotic environment. Thus there exists an alternative pathway of biodegradation which includes transesterification or demethylation by microorganisms, if the
838:
Some data suggest that exposure to multiple phthalates at low doses significantly increases the risk in a dose additive manner. Therefore, the risk from a mixture of phthalates or phthalates and other anti-androgens, may not be accurately assessed studying one chemical at a time. The same may be
830:. The amount of skeletal malformations was highest at highest dose. In a following study it was found that both phthalate diesters and their metabolic products were present in each of these compartments, suggesting that the toxicity in embryos and fetuses could be the result of a direct effect.
496:
839:
said about risks from several exposure routes together. Humans are exposed to phthalates by multiple exposure routes (predominantly dermal), while toxicological testing is done via oral exposure.
1001:
Saito, T.; Peng, H.; Tanabe, R.; Nagai, K.; Kato, K. (December 2010). "Enzymatic hydrolysis of structurally diverse phthalic acid esters by porcine and bovine pancreatic cholesterol esterases".
752:, that would produce another three intermediate compounds, ethyl methyl phthalate, dimethyl phthalate and monomethyl phthalate. This biodegradation has been observed in several soil
685:. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water.
783:
of diethyl phthalate, but existing information suggests only a low toxic potential. Studies suggest that some phthalates affect male reproductive development via inhibition of
764:
Recent studies show that DEP, a phthalic acid ester (PAE), is enzymatically hydrolyzed to its monoesters by pancreatic cholesterol esterase (CEase) in pigs and cows. These
1238:
L. Earl Gray Jr; et al. (2000). "Perinatal
Exposure to the Phthalates DEHP, BBP, and DINP, but Not DEP, DMP, or DOTP, Alters Sexual Differentiation of the Male Rat".
826:
When pregnant rats were treated with diethyl phthalate, it became evident that certain doses caused skeletal malformations, whereas the untreated control group showed no
799:
in male rats. Dose response experiments in fiddler crabs have shown that seven-day exposure to diethyl phthalate at 50 mg/L significantly inhibited the activity of
499:
1111:"Integrating Biomonitoring Exposure Data into the Risk Assessment Process: Phthalates [Diethyl Phthalate and Di(2-ethylhexyl) Phthalate] as a Case Study"
856:
908:
579:
652:
1456:"A Mixture of Five Phthalate Esters Inhibits Fetal Testicular Testosterone Production in the Sprague-Dawley Rat in a Cumulative, Dose-Additive Manner"
521:
1497:"Mechanisms of action of phthalate esters, individually and in combination, to induce abnormal reproductive development in male laboratory rats"
1419:
L. Earl Gray Jr; et al. (2006). "Adverse effects of environmental antiandrogens and androgens on reproductive development in mammals".
1328:
800:
332:
1384:
A. R. Singh; W. H. Lawrence; J. Autian (1975). "Maternal-Fetal transfer of C-Di-2-ethylhexyl phthalate and C-diethyl phthalate in rats".
514:
1319:
1199:
P. M. D. Foster; et al. (1981). "Studies on the testicular effects and zinc excretion produced by various isomers of monobutyl-
1279:)-octylphenol, and 2,4,5-trichlorobiphenyl on activity of chitobiase in the epidermis and hepatopancreas of the fiddler crab,
647:
922:
Api, A.M. (February 2001). "Toxicological profile of diethyl phthalate: a vehicle for fragrance and cosmetic ingredients".
867:
1164:
771:
CEases have been found to be nonspecific for degradation in relation to the diversity of the alkyl side chains of PAEs.
1158:
Paul M. D. Foster; et al. (1980). "Study of the testicular effects and changes in zinc excretion produced by some
105:
297:
659:
507:
1620:
1549:"Environmental phthalate exposure in relation to reproductive outcomes and other health endpoints in humans"
240:
183:
261:
145:
603:
590:
1615:
1318:
M. A. Baars & S.S. Oosterhuis, "Free chitobiase, a marker enzyme for the growth of crustaceans",
278:
462:
1240:
796:
165:
1610:
1349:
A. R. Singh; W. H. Lawrence; J. Autian (1972). "Teratogenicity of
Phthalate Esters in Rats".
438:
1560:
1508:
1010:
249:
45:
8:
1332:
71:
1564:
1512:
1014:
282:
187:
125:
81:
1581:
1548:
1135:
1110:
1086:
1073:
1053:
1034:
787:
biosynthesis. In rats, for instance, repeated administration of DEP results in loss of
698:
1296:
1022:
975:
958:
935:
1586:
1526:
1477:
1436:
1432:
1401:
1366:
1300:
1257:
1220:
1216:
1181:
1177:
1140:
1091:
1026:
980:
939:
1275:
Zou, Enmin; Fingerman, Milton (1999). "Effects of exposure to diethyl phthalate, 4-(
1576:
1568:
1516:
1467:
1428:
1393:
1358:
1292:
1249:
1212:
1173:
1130:
1122:
1081:
1065:
1038:
1018:
970:
931:
780:
427:
355:
1572:
1521:
827:
543:
229:
804:
740:
630:
451:
1253:
904:
567:
279:
DTXSID50892134, DTXSID201024388 DTXSID7021780, DTXSID50892134, DTXSID201024388
1604:
416:
406:
306:
InChI=1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3
176:
1472:
1455:
316:
InChI=1/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3
32:
1590:
1530:
1481:
1440:
1397:
1362:
1304:
1261:
1144:
1054:"Toxicity and health threats of phthalate esters: review of the literature"
1030:
984:
943:
1405:
1370:
1224:
1185:
1095:
520:
1544:
811:
716:
533:
506:
23:
1077:
768:
744:
513:
378:
156:
1126:
788:
765:
679:
1496:
1069:
629:
Except where otherwise noted, data are given for materials in their
815:
784:
753:
749:
702:
479:
204:
1383:
1348:
1108:
902:
104:
724:
694:
396:
216:
1000:
959:"Biodegradation of diethyl phthalate in soil by a novel pathway"
708:
808:
807:. Chitobiase plays an important role in degradation of the old
792:
136:
1317:
682:
116:
94:
266:
616:
195:
720:
909:
National
Institute for Occupational Safety and Health
723:, it has also been used as a blender and fixative in
1494:
1453:
857:"Chemical Information Profile for Diethyl Phthalate"
735:
1157:
693:Diethyl phthalate is produced by the reaction of
1602:
228:
1418:
1237:
1198:
495:
80:
1543:
1109:Antonia M. Calafat; Richard H. McKee (2006).
688:
1329:Royal Netherlands Institute for Sea Research
1274:
795:. However, diethyl phthalate does not alter
759:
707:
538:161.1 °C (322.0 °F; 434.2 K)
1495:Kembra L. Howdeshell; et al. (2008).
1454:Kembra L. Howdeshell; et al. (2008).
956:
281:
186:
164:
1580:
1520:
1471:
1285:Comparative Biochemistry and Physiology C
1134:
1085:
1051:
974:
950:
248:
1102:
903:NIOSH Pocket Guide to Chemical Hazards.
1331:, Texel, pp. 62–64, archived from
996:
994:
833:
277:
1603:
1537:
898:
896:
894:
892:
890:
888:
421:295 °C (563 °F; 568 K)
177:
309:Key: FLKPEMZONWLCSK-UHFFFAOYSA-N
144:
124:
991:
743:of DEP in soil occurs by sequential
411:−4 °C (25 °F; 269 K)
1165:Toxicology and Applied Pharmacology
921:
885:
701:, in the presence of a strong acid
319:Key: FLKPEMZONWLCSK-UHFFFAOYAV
219:
203:
13:
1421:International Journal of Andrology
1386:Journal of Pharmaceutical Sciences
1351:Journal of Pharmaceutical Sciences
864:Integrated Laboratory Systems, Inc
849:
715:It finds some use as a specialist
491:
14:
1632:
1115:Environmental Health Perspectives
1058:Environmental Health Perspectives
1023:10.1016/j.chemosphere.2010.08.020
821:
730:
50:Diethyl benzene-1,2-dicarboxylate
1433:10.1111/j.1365-2605.2005.00636.x
736:Biodegradation by microorganisms
637:
31:
22:
1488:
1447:
1412:
1377:
1342:
1311:
1268:
1231:
1205:Chemico-Biological Interactions
1162:-alkyl phthalates in the rat".
957:Cartwright, C.D. (March 2000).
748:soil is also contaminated with
633:(at 25 °C , 100 kPa).
383:222.24 g/mol
1192:
1151:
1045:
915:
1:
1297:10.1016/S0742-8413(98)10093-2
976:10.1016/S0378-1097(00)00111-7
936:10.1016/s0278-6915(00)00124-1
842:
584:(US health exposure limits):
456:0.002 mmHg (25 °C)
433:1080 mg/L at 25 °C
401:1.12 g/cm at 20 °C
1573:10.1016/j.envres.2008.08.007
1522:10.1016/j.envres.2008.08.009
1217:10.1016/0009-2797(81)90134-4
1178:10.1016/0041-008X(80)90165-9
924:Food and Chemical Toxicology
7:
774:
556:or concentration (LD, LC):
10:
1637:
779:Little is known about the
689:Synthesis and applications
963:FEMS Microbiology Letters
760:Biodegradation by mammals
627:
578:
552:
473:
348:
328:
293:
64:
56:
44:
39:
30:
21:
1203:-phthalate in the rat".
391:Colourless, oily liquid
340:CCOC(=O)c1ccccc1C(=O)OCC
1321:NIOZ Annual Report 2006
1254:10.1093/toxsci/58.2.350
463:Magnetic susceptibility
1553:Environmental Research
1501:Environmental Research
1460:Toxicological Sciences
1398:10.1002/jps.2600640819
1363:10.1002/jps.2600610107
1241:Toxicological Sciences
797:sexual differentiation
712:
574:8600 mg/kg (rat)
502:
469:−127.5·10 cm/mol
1473:10.1093/toxsci/kfn077
803:in the epidermis and
711:
501:
1621:Endocrine disruptors
834:Future investigation
484:(fire diamond)
46:Preferred IUPAC name
1565:2008ER....108..177S
1513:2008ER....108..168H
1015:2010Chmsp..81.1544S
791:populations in the
428:Solubility in water
18:
1052:J. Autian (1973).
873:on 1 February 2009
713:
699:phthalic anhydride
660:Infobox references
619:(Immediate danger)
503:
17:Diethyl phthalate
16:
1121:(11): 1783–1789.
672:Diethyl phthalate
668:Chemical compound
666:
665:
262:CompTox Dashboard
106:Interactive image
59:Diethyl phthalate
1628:
1616:Phthalate esters
1595:
1594:
1584:
1541:
1535:
1534:
1524:
1492:
1486:
1485:
1475:
1451:
1445:
1444:
1416:
1410:
1409:
1392:(8): 1347–1350.
1381:
1375:
1374:
1346:
1340:
1339:
1337:
1326:
1315:
1309:
1308:
1272:
1266:
1265:
1235:
1229:
1228:
1196:
1190:
1189:
1155:
1149:
1148:
1138:
1127:10.1289/ehp.9059
1106:
1100:
1099:
1089:
1049:
1043:
1042:
1009:(1): 1544–1548.
998:
989:
988:
978:
954:
948:
947:
919:
913:
912:
900:
883:
882:
880:
878:
872:
866:. Archived from
861:
853:
781:chronic toxicity
650:
644:
641:
640:
610:TWA 5 mg/m
544:Explosive limits
523:
516:
509:
494:
356:Chemical formula
286:
285:
270:
268:
252:
232:
221:
207:
190:
179:
168:
148:
128:
108:
84:
35:
26:
19:
15:
1636:
1635:
1631:
1630:
1629:
1627:
1626:
1625:
1601:
1600:
1599:
1598:
1542:
1538:
1493:
1489:
1452:
1448:
1417:
1413:
1382:
1378:
1347:
1343:
1335:
1324:
1316:
1312:
1273:
1269:
1236:
1232:
1197:
1193:
1156:
1152:
1107:
1103:
1070:10.2307/3428178
1050:
1046:
999:
992:
955:
951:
920:
916:
901:
886:
876:
874:
870:
859:
855:
854:
850:
845:
836:
824:
814:during the pre-
777:
762:
738:
733:
691:
669:
662:
657:
656:
655: ?)
646:
642:
638:
634:
620:
607:
594:
571:
565:
528:
527:
526:
525:
518:
511:
504:
500:
492:
466:
430:
372:
368:
364:
358:
344:
341:
336:
335:
324:
321:
320:
317:
311:
310:
307:
301:
300:
289:
271:
264:
255:
235:
222:
210:
171:
151:
131:
111:
98:
87:
74:
60:
52:
51:
12:
11:
5:
1634:
1624:
1623:
1618:
1613:
1597:
1596:
1559:(2): 177–184.
1545:Shanna H. Swan
1536:
1507:(2): 168–176.
1487:
1466:(1): 153–165.
1446:
1411:
1376:
1341:
1310:
1291:(1): 115–120.
1267:
1248:(2): 350–365.
1230:
1211:(2): 233–238.
1191:
1172:(3): 392–398.
1150:
1101:
1044:
990:
949:
914:
884:
847:
846:
844:
841:
835:
832:
823:
822:Teratogenicity
820:
805:hepatopancreas
776:
773:
761:
758:
741:Biodegradation
737:
734:
732:
731:Biodegradation
729:
690:
687:
667:
664:
663:
658:
636:
635:
631:standard state
628:
625:
624:
621:
615:
612:
611:
608:
602:
599:
598:
595:
589:
586:
585:
576:
575:
572:
563:
561:
558:
557:
550:
549:
546:
540:
539:
536:
530:
529:
519:
512:
505:
490:
489:
488:
487:
485:
476:
475:
471:
470:
467:
461:
458:
457:
454:
452:Vapor pressure
448:
447:
444:
435:
434:
431:
426:
423:
422:
419:
413:
412:
409:
403:
402:
399:
393:
392:
389:
385:
384:
381:
375:
374:
370:
366:
362:
359:
354:
351:
350:
346:
345:
343:
342:
339:
331:
330:
329:
326:
325:
323:
322:
318:
315:
314:
312:
308:
305:
304:
296:
295:
294:
291:
290:
288:
287:
274:
272:
260:
257:
256:
254:
253:
245:
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237:
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234:
233:
225:
223:
215:
212:
211:
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208:
200:
198:
192:
191:
181:
173:
172:
170:
169:
161:
159:
153:
152:
150:
149:
141:
139:
133:
132:
130:
129:
121:
119:
113:
112:
110:
109:
101:
99:
92:
89:
88:
86:
85:
77:
75:
70:
67:
66:
62:
61:
58:
54:
53:
49:
48:
42:
41:
37:
36:
28:
27:
9:
6:
4:
3:
2:
1633:
1622:
1619:
1617:
1614:
1612:
1609:
1608:
1606:
1592:
1588:
1583:
1578:
1574:
1570:
1566:
1562:
1558:
1554:
1550:
1546:
1540:
1532:
1528:
1523:
1518:
1514:
1510:
1506:
1502:
1498:
1491:
1483:
1479:
1474:
1469:
1465:
1461:
1457:
1450:
1442:
1438:
1434:
1430:
1427:(1): 96–104.
1426:
1422:
1415:
1407:
1403:
1399:
1395:
1391:
1387:
1380:
1372:
1368:
1364:
1360:
1356:
1352:
1345:
1338:on 2011-07-20
1334:
1330:
1323:
1322:
1314:
1306:
1302:
1298:
1294:
1290:
1286:
1282:
1281:Uca pugilator
1278:
1271:
1263:
1259:
1255:
1251:
1247:
1243:
1242:
1234:
1226:
1222:
1218:
1214:
1210:
1206:
1202:
1195:
1187:
1183:
1179:
1175:
1171:
1167:
1166:
1161:
1154:
1146:
1142:
1137:
1132:
1128:
1124:
1120:
1116:
1112:
1105:
1097:
1093:
1088:
1083:
1079:
1075:
1071:
1067:
1063:
1059:
1055:
1048:
1040:
1036:
1032:
1028:
1024:
1020:
1016:
1012:
1008:
1004:
997:
995:
986:
982:
977:
972:
968:
964:
960:
953:
945:
941:
937:
933:
930:(2): 97–108.
929:
925:
918:
910:
906:
899:
897:
895:
893:
891:
889:
869:
865:
858:
852:
848:
840:
831:
829:
819:
817:
813:
810:
806:
802:
798:
794:
790:
786:
782:
772:
770:
767:
757:
755:
751:
746:
742:
728:
726:
722:
718:
710:
706:
704:
700:
696:
686:
684:
681:
677:
673:
661:
654:
649:
632:
626:
622:
618:
614:
613:
609:
606:(Recommended)
605:
601:
600:
596:
593:(Permissible)
592:
588:
587:
583:
582:
577:
573:
569:
560:
559:
555:
551:
547:
545:
542:
541:
537:
535:
532:
531:
524:
517:
510:
486:
483:
482:
478:
477:
472:
468:
464:
460:
459:
455:
453:
450:
449:
445:
443:
442:
437:
436:
432:
429:
425:
424:
420:
418:
417:Boiling point
415:
414:
410:
408:
407:Melting point
405:
404:
400:
398:
395:
394:
390:
387:
386:
382:
380:
377:
376:
360:
357:
353:
352:
347:
338:
337:
334:
327:
313:
303:
302:
299:
292:
284:
280:
276:
275:
273:
263:
259:
258:
251:
247:
246:
244:
242:
239:
238:
231:
227:
226:
224:
218:
214:
213:
206:
202:
201:
199:
197:
194:
193:
189:
185:
182:
180:
178:ECHA InfoCard
175:
174:
167:
163:
162:
160:
158:
155:
154:
147:
143:
142:
140:
138:
135:
134:
127:
123:
122:
120:
118:
115:
114:
107:
103:
102:
100:
96:
91:
90:
83:
79:
78:
76:
73:
69:
68:
63:
55:
47:
43:
38:
34:
29:
25:
20:
1611:Ethyl esters
1556:
1552:
1539:
1504:
1500:
1490:
1463:
1459:
1449:
1424:
1420:
1414:
1389:
1385:
1379:
1357:(1): 51–55.
1354:
1350:
1344:
1333:the original
1320:
1313:
1288:
1284:
1280:
1276:
1270:
1245:
1239:
1233:
1208:
1204:
1200:
1194:
1169:
1163:
1159:
1153:
1118:
1114:
1104:
1061:
1057:
1047:
1006:
1002:
969:(1): 27–34.
966:
962:
952:
927:
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548:0.7%, lower
480:
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146:ChEMBL388558
65:Identifiers
57:Other names
1003:Chemosphere
828:resorptions
812:exoskeleton
717:plasticiser
568:median dose
554:Lethal dose
534:Flash point
388:Appearance
349:Properties
184:100.001.409
126:CHEBI:34698
1605:Categories
843:References
801:chitobiase
769:pancreatic
745:hydrolysis
379:Molar mass
250:UF064M00AF
157:ChemSpider
93:3D model (
72:CAS Number
789:germ cell
766:mammalian
680:phthalate
1591:18949837
1547:(2008).
1531:18949836
1482:18411233
1441:16466529
1305:10190035
1262:11099647
1145:17107868
1064:: 3–25.
1031:20822795
985:10779708
944:11267702
911:(NIOSH).
785:androgen
775:Toxicity
754:bacteria
750:methanol
703:catalyst
481:NFPA 704
474:Hazards
465:(χ)
166:13837303
1582:2775531
1561:Bibcode
1509:Bibcode
1406:1151708
1371:5058645
1225:7460085
1186:7394794
1136:1665433
1096:4578674
1087:1474854
1078:3428178
1039:6958344
1011:Bibcode
905:"#0213"
877:3 March
818:phase.
725:perfume
695:ethanol
678:) is a
653:what is
651: (
397:Density
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217:PubChem
82:84-66-2
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809:chitin
793:testis
648:verify
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333:SMILES
205:D03804
137:ChEMBL
40:Names
1336:(PDF)
1325:(PDF)
1074:JSTOR
1035:S2CID
871:(PDF)
860:(PDF)
816:moult
697:with
683:ester
623:N.D.
597:None
581:NIOSH
446:2.42
298:InChI
117:ChEBI
95:JSmol
1587:PMID
1527:PMID
1478:PMID
1437:PMID
1402:PMID
1367:PMID
1301:PMID
1277:tert
1258:PMID
1221:PMID
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1141:PMID
1092:PMID
1027:PMID
981:PMID
940:PMID
879:2009
617:IDLH
439:log
241:UNII
230:6781
196:KEGG
1577:PMC
1569:doi
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1468:doi
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1283:".
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1131:PMC
1123:doi
1119:114
1082:PMC
1066:doi
1019:doi
971:doi
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932:doi
721:PVC
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676:DEP
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