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171:
33:
601:
24:
462:
690:
Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and
Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq),
669:
receptor on these cells. It is suggested that sebacic acid is converted to its 5-oxo analog during, and thereby stimulates pro-inflammatory cells to contribute to the worsening of, various inflammatory skin conditions.
1025:
649:
and sebacic acid. Sebacic acid is also found in other lipids that coat the skin surface. Human neutrophils can convert sebacic acid to its 5-oxo analog, i.e., 5-oxo-6E,8Z-octadecenoic acid, a
475:
1011:
780:
Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons".
782:
747:
327:
1018:
292:
551:
It can be used as a surfactant in the lubricating oil industry to increase the antirust properties of lubricating oils on metals.
898:"Mammalian Wax Biosynthesis II: Expression cloning of wax synthase cDNAs encoding a member of the acyltransferase enzyme family"
799:
764:
604:
Conversion of dimethyl ester of sebacic acid to cyclodecanediol by acyloin condensation followed by hydrogenation using a
482:
235:
897:
1295:
1276:
654:
256:
646:
433:
108:
178:
605:
196:
815:
Seko, Maomi; Yomiyama, Akira; Isoya, Toshiro (1979). "Development of Kolbe
Electrosynthesis of Sebacic Acid".
166:
529:
is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of
202:
45:
1003:
273:
74:
1252:
1201:
989:
665:, and other pro-inflammatory cells from humans and other species. This action is mediated by the
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1167:
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1133:
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537:
874:
224:
1115:
1055:
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and like this oxo-eicosatetraenoic acid is an exceptionally potent activator of
642:
594:
967:
861:
Thody, A. J.; Shuster, S. (1989). "Control and
Function of Sebaceous Glands".
634:
560:
530:
378:
139:
847:
791:
756:
301:
InChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)
662:
311:
InChI=1/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)
985:
936:
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23:
638:
572:
579:
568:
391:
211:
179:
728:
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406:
131 to 134.5 °C (267.8 to 274.1 °F; 404.1 to 407.6 K)
952:"Targeting the OXE receptor as a potential novel therapy for asthma"
745:
Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic".
452:
Except where otherwise noted, data are given for materials in their
834:
Blomquist, A. T.; Goldstein, Albert (1956). "1,2-Cyclodecanediol".
536:
In the industrial setting, sebacic acid and its homologues such as
666:
599:
541:
119:
107:
97:
645:(≈16%). Included in the free fatty acid secretions in sebum are
1007:
622:
261:
586:, which gives cyclodecenone, a precursor to sebacic acid.
416:
294.4 °C (561.9 °F; 567.5 K) at 100 mmHg
470:
589:
Sebacic acid has also been produced commercially by
223:
817:CEER, Chemical Economy & Engineering Review
83:
783:Ullmann's Encyclopedia of Industrial Chemistry
748:Ullmann's Encyclopedia of Industrial Chemistry
1019:
8:
711:NI(aq) at Different Ionic Strengths and at
1026:
1012:
1004:
740:
738:
276:
169:
147:
15:
975:
926:
916:
521:. It is a white flake or powdered solid.
243:
516:
512:
508:
504:
896:Cheng JB, Russell DW (September 2004).
679:
332:
297:
272:
201:
160:
685:
683:
567:, which is obtained from castor oil.
304:Key: CXMXRPHRNRROMY-UHFFFAOYSA-N
127:
7:
1035:Linear saturated dicarboxylic acids
905:The Journal of Biological Chemistry
314:Key: CXMXRPHRNRROMY-UHFFFAOYAE
214:
950:Powell WS, Rokach J (March 2020).
14:
460:
362:
31:
22:
544:610, plasticizers, lubricants,
456:(at 25 °C , 100 kPa).
613:Potential medical significance
559:Sebacic acid is produced from
368:
356:
1:
875:10.1152/physrev.1989.69.2.383
617:Sebum is a secretion by skin
578:It can also be obtained from
540:can be used as a monomer for
525:is Latin for tallow candle,
1277:Category:Dicarboxylic acids
655:5-oxo-eicosatetraenoic acid
647:polyunsaturated fatty acids
548:, cosmetics, candles, etc.
59:1,8-Octanedicarboxylic acid
1312:
501:with the chemical formula
1274:
1236:Hexadecanedioic acid
1050:
968:10.1016/j.bcp.2020.113930
497:is a naturally occurring
450:
343:
323:
288:
67:
56:
44:
39:
30:
21:
1255:(Phelogenic acid) C
1219:Tredecanedioic acid
956:Biochemical Pharmacology
848:10.15227/orgsyn.036.0012
792:10.1002/14356007.a13_227
757:10.1002/14356007.a08_523
606:copper chromite catalyst
555:Production and reactions
1202:Dodecanedioic acid
786:. Weinheim: Wiley-VCH.
751:. Weinheim: Wiley-VCH.
1134:Heptanedioic acid
1100:(Glutaric acid) C
1098:Pentanedioic acid
1082:(Succinic acid) C
1068:(Malonic acid) CH
1066:Propanedioic acid
1058:(Oxalic acid) (CO
918:10.1074/jbc.M406226200
609:
61:Decane-1,10-dioic acid
1238:(Thapsic acid) C
1187:(Sebacic acid) C
1185:Decanedioic acid
1170:(Azelaic acid) C
1168:Nonanedioic acid
1153:(Suberic acid) C
1151:Octanedioic acid
1136:(Pimelic acid) C
1116:Hexanedioic acid
1080:Butanedioic acid
1056:Ethanedioic acid
863:Physiological Reviews
603:
1118:(Adipic acid) C
335:OC(=O)CCCCCCCCC(=O)O
46:Preferred IUPAC name
575:are byproducts.
423:Solubility in water
386: g·mol
18:
1296:Dicarboxylic acids
1253:Docosanedioic acid
1221:(Brassylic acid) C
717:J. Chem. Eng. Data
610:
591:Kolbe electrolysis
483:Infobox references
16:
1283:
1282:
911:(36): 37798–807.
836:Organic Syntheses
729:10.1021/je060132t
651:structural analog
582:via the tertiary
499:dicarboxylic acid
491:Chemical compound
489:
488:
257:CompTox Dashboard
109:Interactive image
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723:(5): 1660–1667.
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643:free fatty acids
619:sebaceous glands
546:hydraulic fluids
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351:Chemical formula
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50:Decanedioic acid
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699:NCl(aq), and (C
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565:ricinoleic acid
563:by cleavage of
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454:standard state
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631:triglycerides
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584:hydroperoxide
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446:4.720, 5.450
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412:Boiling point
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161:ECHA InfoCard
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17:Sebacic acid
1184:
959:
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712:
641:(≈12%), and
629:composed of
616:
588:
577:
558:
550:
538:azelaic acid
535:
526:
522:
495:Sebacic acid
494:
493:
437:
68:Identifiers
57:Other names
823:(9): 48-50.
659:eosinophils
595:adipic acid
396:1.209 g/cm
344:Properties
167:100.003.496
129:CHEBI:41865
962:: 113930.
801:3527306730
766:3527306730
715:= 25 °C".
674:References
635:wax esters
621:. It is a
561:castor oil
531:castor oil
379:Molar mass
245:97AN39ICTC
140:ChemSpider
96:3D model (
75:CAS Number
994:214768793
663:monocytes
428:0.25 g/L
188:203-845-5
180:EC Number
1290:Category
986:32240653
977:10656995
937:15220349
639:squalene
637:(≈26%),
633:(≈41%),
573:glycerin
523:Sebaceus
85:111-20-6
928:2743083
883:2648418
625:set of
580:decalin
569:Octanol
476:what is
474: (
434:Acidity
392:Density
384:202.250
212:PubChem
203:C011107
1041:C-R-CO
992:
984:
974:
935:
925:
881:
842:: 12.
798:
763:
627:lipids
471:verify
468:
328:SMILES
40:Names
990:S2CID
901:(PDF)
667:OXER1
542:nylon
527:sebum
293:InChI
120:ChEBI
98:JSmol
982:PMID
933:PMID
879:PMID
796:ISBN
761:ISBN
623:waxy
571:and
507:C(CH
236:UNII
225:5192
197:MeSH
149:5004
1126:(CO
1108:(CO
1090:(CO
1072:(CO
1037:(HO
972:PMC
964:doi
960:179
923:PMC
913:doi
909:279
871:doi
844:doi
788:doi
753:doi
725:doi
691:(CH
653:of
593:of
262:EPA
215:CID
1292::
1261:42
1257:22
1244:30
1240:16
1227:24
1223:13
1210:22
1206:12
1193:18
1189:10
1176:16
1159:14
1142:12
1130:H)
1112:H)
1094:H)
1076:H)
1062:H)
1045:H)
988:.
980:.
970:.
958:.
954:.
931:.
921:.
907:.
903:.
877:.
867:69
865:.
840:36
838:.
821:11
819:.
794:.
759:.
737:^
721:51
719:.
682:^
661:,
608:.
597:.
533:.
515:CO
503:HO
443:)
436:(p
366:18
360:10
1265:4
1263:O
1259:H
1248:4
1246:O
1242:H
1231:4
1229:O
1225:H
1214:4
1212:O
1208:H
1204:C
1197:4
1195:O
1191:H
1180:4
1178:O
1174:H
1172:9
1163:4
1161:O
1157:H
1155:8
1146:4
1144:O
1140:H
1138:7
1128:2
1124:8
1122:H
1120:4
1110:2
1106:6
1104:H
1102:3
1092:2
1088:4
1086:H
1084:2
1074:2
1070:2
1060:2
1043:2
1039:2
1027:e
1020:t
1013:v
996:.
966::
939:.
915::
885:.
873::
850:.
846::
804:.
790::
769:.
755::
731:.
727::
713:t
709:4
707:)
705:5
703:H
701:2
697:4
695:)
693:3
519:H
517:2
513:8
511:)
509:2
505:2
466:N
441:a
438:K
372:4
369:O
363:H
357:C
264:)
260:(
100:)
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