252:
26:
376:
389:
547:"Deficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus"
301:
891:
601:
266:
863:
487:, is also present in sebum. Sapienic acid can lead to the decanal which is likely what mosquitoes use to identify human prey.
1275:
1269:
396:
209:
1215:
113:
676:"Palmitic acid (16:0) competes with omega-6 linoleic and omega-3 ɑ-linolenic acids for FADS2 mediated Δ6-desaturation"
230:
1340:
1411:
1328:
1209:
1203:
1239:
805:
Zhao Z, Zung JL, Kriete AL, Iqbal A, Younger MA, Matthews BJ, Merhof D, Thiberge S, Strauch M, McBride CS (2020).
506:"Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis"
1478:
1334:
884:
1197:
483:, allowing the enzyme to desaturate palmitic to sapienic acid. A two-carbon extension product of sapienic acid,
1531:
1633:
1185:
1136:
1130:
1124:
1191:
807:"Chemical signatures of human odour generate a unique neural code in the brain of Aedes aegypti mosquitoes"
1405:
1365:
1359:
1300:
1173:
1594:
1586:
1567:
1548:
1142:
275:
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h10-11H,2-9,12-15H2,1H3,(H,17,18)/b11-10-
1435:
1429:
1286:
1257:
1251:
1245:
1118:
833:
456:
285:
InChI=1/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h10-11H,2-9,12-15H2,1H3,(H,17,18)/b11-10-
1606:
1312:
1306:
1179:
806:
1628:
1387:
1263:
1167:
1161:
1088:
877:
630:
38:
766:"Identification of the delta-6 desaturase of human sebaceous glands: expression and enzyme activity"
247:
1233:
1221:
484:
79:
1513:
1489:
1446:
1351:
1153:
821:
574:
468:
462:
1600:
1377:
1052:
1028:
992:
787:
746:
705:
656:
597:
566:
527:
447:
153:
1454:
1423:
1294:
1227:
1112:
1076:
1016:
813:
777:
736:
695:
687:
646:
638:
558:
517:
428:
424:
324:
218:
89:
1064:
1046:
1040:
980:
956:
846:
617:
Neumann Y, Ohlsen K, Donat S, Engelmann S, Kusch H, Albrecht D, et al. (March 2015).
480:
674:
Park HG, Kothapalli KS, Park WJ, DeAllie C, Liu L, Liang A, et al. (February 2016).
251:
725:"Metabolic fate and selective utilization of major fatty acids in human sebaceous gland"
634:
133:
1472:
1417:
1399:
1094:
1022:
968:
920:
700:
675:
651:
618:
440:
367:
1622:
1575:
1525:
1460:
1393:
1371:
1082:
1070:
1004:
998:
986:
950:
944:
912:
825:
782:
765:
741:
724:
522:
505:
476:
472:
451:
198:
1503:
1466:
1322:
1100:
1058:
1034:
1010:
938:
932:
926:
578:
64:
691:
1519:
1106:
974:
962:
546:
446:
Deficient production of sapienic acid has been implicated in the development of
1497:
904:
817:
642:
412:
352:
144:
1537:
791:
750:
709:
660:
570:
531:
25:
680:
Biochimica et
Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids
596:. Basic and clinical dermatology. Vol. 40. CRC Press. p. 311.
479:
is the target for delta 6 desaturase, but linoleic acid is degraded in
185:
869:
562:
366:
Except where otherwise noted, data are given for materials in their
173:
900:
436:
432:
416:
124:
112:
102:
419:. Unique to humans, it takes its scientific name from the root
164:
873:
465:
intake has been linked to lower sapienic acid levels in sebum.
545:
Takigawa H, Nakagawa H, Kuzukawa M, Mori H, Imokawa G (2005).
475:
leads to the biosynthesis of sapienic acid. In other tissues
235:
764:
Ge L, Gordon JS, Hsuan C, Stenn K, Prouty SM (May 2003).
619:"The effect of skin fatty acids on Staphylococcus aureus"
384:
1585:
1566:
1547:
1488:
1445:
1350:
1285:
1152:
911:
723:Pappas A, Anthonavage M, Gordon JS (January 2002).
504:Katsuta Y, Iida T, Inomata S, Denda M (May 2005).
197:
88:
423:. The equivalent fatty acid in mouse sebum is
885:
8:
892:
878:
870:
250:
152:
17:
781:
740:
699:
650:
521:
217:
770:The Journal of Investigative Dermatology
729:The Journal of Investigative Dermatology
592:Webster GF, Anthony V. Rawlings (2007).
510:The Journal of Investigative Dermatology
516:(5). Nature Publishing Group: 1008–13.
496:
306:
271:
246:
842:
831:
776:(5). Nature Publishing Group: 707–14.
735:(1). Nature Publishing Group: 164–71.
278:Key: NNNVXFKZMRGJPM-KHPPLWFESA-N
132:
7:
415:that is a major component of human
288:Key: NNNVXFKZMRGJPM-KHPPLWFEBD
188:
172:
1276:6,9,12,15,18,21-Tetracosahexaenoic
14:
1270:9,12,15,18,21-Tetracosapentaenoic
783:10.1046/j.1523-1747.2003.12123.x
742:10.1046/j.0022-202x.2001.01612.x
523:10.1111/j.0022-202X.2005.23682.x
454:activity against pathogens like
374:
336:
24:
450:, and sapienic acid has potent
370:(at 25 °C , 100 kPa).
342:
330:
1:
692:10.1016/j.bbalip.2015.11.007
1650:
818:10.1101/2020.11.01.363861
643:10.1007/s00203-014-1048-1
443:are known as sapienates.
364:
317:
297:
262:
72:
53:
37:
32:
23:
1329:7,10,13-Octadecatrienoic
623:Archives of Microbiology
309:O=C(O)CCCC\C=C/CCCCCCCCC
1479:7,10,13-Eicosatrienoic
1335:9,12,15-Eicosatrienoic
841:Cite journal requires
47:)-Hexadec-6-enoic acid
457:Staphylococcus aureus
594:Acne and Its Therapy
469:Delta-6-desaturation
59:-6-Hexadecenoic acid
39:Preferred IUPAC name
866:, The Lipid Library
635:2015ArMic.197..245N
360: g·mol
20:
1532:8,11-Eicosadienoic
1412:Dihomo-γ-linolenic
1341:β-Eicosatetraenoic
1240:Dihomo-α-linolenic
1125:Heptatriacontanoic
397:Infobox references
18:
1616:
1615:
1137:Nonatriacontanoic
1131:Octatriacontanoic
603:978-0-8247-2971-4
563:10.1159/000087018
448:atopic dermatitis
405:Chemical compound
403:
402:
231:CompTox Dashboard
114:Interactive image
1641:
1587:ω−12 Unsaturated
1568:ω−11 Unsaturated
1549:ω−10 Unsaturated
1252:Eicosapentaenoic
1246:Eicosatetraenoic
1210:Palmitolinolenic
1204:Myristolinolenic
1119:Hexatriacontylic
894:
887:
880:
871:
851:
850:
844:
839:
837:
829:
811:
802:
796:
795:
785:
761:
755:
754:
744:
720:
714:
713:
703:
671:
665:
664:
654:
614:
608:
607:
589:
583:
582:
542:
536:
535:
525:
501:
427:. Sapienic acid
425:palmitoleic acid
387:
381:
378:
377:
359:
344:
338:
332:
325:Chemical formula
255:
254:
239:
237:
221:
201:
190:
176:
156:
136:
116:
92:
28:
21:
1649:
1648:
1644:
1643:
1642:
1640:
1639:
1638:
1619:
1618:
1617:
1612:
1581:
1562:
1543:
1490:ω−9 Unsaturated
1484:
1447:ω−7 Unsaturated
1441:
1406:Dihomo-linoleic
1366:12-Octadecenoic
1360:8-Tetradecenoic
1352:ω−6 Unsaturated
1346:
1301:Palmitovaccenic
1287:ω−5 Unsaturated
1281:
1264:Docosahexaenoic
1198:Myristolinoleic
1192:Myristovaccenic
1154:ω−3 Unsaturated
1148:
1089:Hentriacontylic
907:
898:
860:
855:
854:
840:
830:
809:
804:
803:
799:
763:
762:
758:
722:
721:
717:
673:
672:
668:
616:
615:
611:
604:
591:
590:
586:
544:
543:
539:
503:
502:
498:
493:
481:sebaceous cells
406:
399:
394:
393:
392: ?)
383:
379:
375:
371:
357:
347:
341:
335:
327:
313:
310:
305:
304:
293:
290:
289:
286:
280:
279:
276:
270:
269:
258:
240:
233:
224:
204:
191:
179:
159:
139:
119:
106:
95:
82:
68:
62:
60:
49:
48:
12:
11:
5:
1647:
1645:
1637:
1636:
1634:Alkenoic acids
1631:
1621:
1620:
1614:
1613:
1611:
1610:
1604:
1598:
1595:4-Hexadecenoic
1591:
1589:
1583:
1582:
1580:
1579:
1572:
1570:
1564:
1563:
1561:
1560:
1553:
1551:
1545:
1544:
1542:
1541:
1535:
1529:
1523:
1517:
1511:
1501:
1494:
1492:
1486:
1485:
1483:
1482:
1476:
1470:
1464:
1458:
1451:
1449:
1443:
1442:
1440:
1439:
1433:
1427:
1421:
1415:
1409:
1403:
1397:
1391:
1385:
1375:
1369:
1363:
1356:
1354:
1348:
1347:
1345:
1344:
1338:
1332:
1326:
1320:
1310:
1304:
1298:
1291:
1289:
1283:
1282:
1280:
1279:
1273:
1267:
1261:
1255:
1249:
1243:
1237:
1231:
1225:
1219:
1213:
1207:
1201:
1195:
1189:
1183:
1177:
1171:
1165:
1158:
1156:
1150:
1149:
1147:
1146:
1143:Tetracontanoic
1140:
1134:
1128:
1122:
1116:
1110:
1104:
1098:
1092:
1086:
1080:
1074:
1068:
1062:
1056:
1050:
1044:
1038:
1032:
1026:
1020:
1014:
1008:
1002:
996:
990:
984:
978:
972:
966:
960:
954:
948:
942:
936:
930:
924:
917:
915:
909:
908:
899:
897:
896:
889:
882:
874:
868:
867:
859:
858:External links
856:
853:
852:
843:|journal=
797:
756:
715:
666:
609:
602:
584:
537:
495:
494:
492:
489:
441:conjugate base
404:
401:
400:
395:
373:
372:
368:standard state
365:
362:
361:
355:
349:
348:
345:
339:
333:
328:
323:
320:
319:
315:
314:
312:
311:
308:
300:
299:
298:
295:
294:
292:
291:
287:
284:
283:
281:
277:
274:
273:
265:
264:
263:
260:
259:
257:
256:
248:DTXSID50904584
243:
241:
229:
226:
225:
223:
222:
214:
212:
206:
205:
203:
202:
194:
192:
184:
181:
180:
178:
177:
169:
167:
161:
160:
158:
157:
149:
147:
141:
140:
138:
137:
129:
127:
121:
120:
118:
117:
109:
107:
100:
97:
96:
94:
93:
85:
83:
78:
75:
74:
70:
69:
55:
51:
50:
42:
41:
35:
34:
30:
29:
19:Sapienic acid
13:
10:
9:
6:
4:
3:
2:
1646:
1635:
1632:
1630:
1627:
1626:
1624:
1608:
1605:
1602:
1599:
1596:
1593:
1592:
1590:
1588:
1584:
1577:
1574:
1573:
1571:
1569:
1565:
1558:
1555:
1554:
1552:
1550:
1546:
1539:
1536:
1533:
1530:
1527:
1524:
1521:
1518:
1515:
1512:
1509:
1505:
1502:
1499:
1496:
1495:
1493:
1491:
1487:
1480:
1477:
1474:
1471:
1468:
1465:
1462:
1459:
1456:
1453:
1452:
1450:
1448:
1444:
1437:
1434:
1431:
1428:
1425:
1422:
1419:
1416:
1413:
1410:
1407:
1404:
1401:
1398:
1395:
1392:
1389:
1386:
1383:
1379:
1376:
1373:
1370:
1367:
1364:
1361:
1358:
1357:
1355:
1353:
1349:
1342:
1339:
1336:
1333:
1330:
1327:
1324:
1321:
1318:
1314:
1313:β-Eleostearic
1311:
1308:
1307:α-Eleostearic
1305:
1302:
1299:
1296:
1293:
1292:
1290:
1288:
1284:
1277:
1274:
1271:
1268:
1265:
1262:
1259:
1256:
1253:
1250:
1247:
1244:
1241:
1238:
1235:
1232:
1229:
1226:
1223:
1220:
1217:
1214:
1211:
1208:
1205:
1202:
1199:
1196:
1193:
1190:
1187:
1186:Laurolinoleic
1184:
1181:
1178:
1175:
1172:
1169:
1166:
1163:
1160:
1159:
1157:
1155:
1151:
1144:
1141:
1138:
1135:
1132:
1129:
1126:
1123:
1120:
1117:
1114:
1111:
1108:
1105:
1102:
1099:
1096:
1093:
1090:
1087:
1084:
1081:
1078:
1075:
1072:
1069:
1066:
1063:
1060:
1057:
1054:
1051:
1048:
1045:
1042:
1039:
1036:
1033:
1030:
1027:
1024:
1021:
1018:
1015:
1012:
1009:
1006:
1003:
1000:
997:
994:
991:
988:
985:
982:
979:
976:
973:
970:
967:
964:
961:
958:
955:
952:
949:
946:
943:
940:
937:
934:
931:
928:
925:
922:
919:
918:
916:
914:
910:
906:
902:
895:
890:
888:
883:
881:
876:
875:
872:
865:
862:
861:
857:
848:
835:
827:
823:
819:
815:
808:
801:
798:
793:
789:
784:
779:
775:
771:
767:
760:
757:
752:
748:
743:
738:
734:
730:
726:
719:
716:
711:
707:
702:
697:
693:
689:
685:
681:
677:
670:
667:
662:
658:
653:
648:
644:
640:
636:
632:
629:(2): 245–67.
628:
624:
620:
613:
610:
605:
599:
595:
588:
585:
580:
576:
572:
568:
564:
560:
556:
552:
548:
541:
538:
533:
529:
524:
519:
515:
511:
507:
500:
497:
490:
488:
486:
485:sebaleic acid
482:
478:
477:linoleic acid
474:
473:palmitic acid
470:
466:
464:
460:
458:
453:
452:antibacterial
449:
444:
442:
438:
434:
430:
426:
422:
418:
414:
410:
409:Sapienic acid
398:
391:
386:
369:
363:
356:
354:
351:
350:
329:
326:
322:
321:
316:
307:
303:
296:
282:
272:
268:
261:
253:
249:
245:
244:
242:
232:
228:
227:
220:
216:
215:
213:
211:
208:
207:
200:
196:
195:
193:
187:
183:
182:
175:
171:
170:
168:
166:
163:
162:
155:
151:
150:
148:
146:
143:
142:
135:
131:
130:
128:
126:
123:
122:
115:
111:
110:
108:
104:
99:
98:
91:
87:
86:
84:
81:
77:
76:
71:
66:
65:lipid numbers
58:
52:
46:
40:
36:
31:
27:
22:
16:
1607:8-Eicosenoic
1601:Petroselinic
1556:
1507:
1381:
1378:Linolelaidic
1316:
1258:Clupanodonic
1216:Palmitidonic
1053:Pentacosylic
1029:Heneicosylic
993:Pentadecylic
834:cite journal
800:
773:
769:
759:
732:
728:
718:
686:(2): 91–97.
683:
679:
669:
626:
622:
612:
593:
587:
557:(3): 240–8.
554:
550:
540:
513:
509:
499:
467:
455:
445:
420:
408:
407:
73:Identifiers
56:
54:Other names
44:
15:
1629:Fatty acids
1455:Palmitoleic
1424:Arachidonic
1388:γ-Linolenic
1295:Myristoleic
1234:α-Parinaric
1228:Stearidonic
1222:α-Linolenic
1174:Decadienoic
1113:Ceroplastic
1077:Nonacosylic
1017:Nonadecylic
905:fatty acids
551:Dermatology
318:Properties
134:CHEBI:76244
1623:Categories
1065:Carboceric
1047:Lignoceric
1041:Tricosylic
981:Tridecylic
957:Pelargonic
491:References
413:fatty acid
353:Molar mass
219:6460S1EJ28
145:ChemSpider
101:3D model (
90:17004-51-2
80:CAS Number
1473:Paullinic
1418:Sciadonic
1400:Pinolenic
1180:Lauroleic
1095:Lacceroic
1023:Arachidic
969:Undecylic
921:Propionic
913:Saturated
826:226263862
63:16:1n10 (
1576:Gadoleic
1557:Sapienic
1526:Nervonic
1461:Vaccenic
1394:Calendic
1372:Linoleic
1168:Decenoic
1162:Octenoic
1083:Melissic
1071:Montanic
1005:Margaric
999:Palmitic
987:Myristic
951:Caprylic
945:Enanthic
792:12713571
751:11851890
710:26597785
661:25325933
571:16205069
532:15854043
461:Reduced
1514:Gondoic
1504:Elaidic
1467:Rumenic
1430:Adrenic
1323:Punicic
1101:Psyllic
1059:Cerotic
1035:Behenic
1011:Stearic
939:Caproic
933:Valeric
927:Butyric
701:4691389
652:4326651
631:Bibcode
579:1574784
463:omega-3
421:sapiens
390:what is
388: (
358:254.414
199:5312419
186:PubChem
154:4471844
61:16:1ω10
1609:(20:1)
1603:(18:1)
1597:(16:1)
1578:(20:1)
1559:(16:1)
1540:(20:3)
1534:(20:2)
1528:(24:1)
1522:(22:1)
1520:Erucic
1516:(20:1)
1510:-18:1)
1500:(18:1)
1481:(20:3)
1475:(20:1)
1469:(18:2)
1463:(18:1)
1457:(16:1)
1438:(22:5)
1436:Osbond
1432:(22:4)
1426:(20:4)
1420:(20:3)
1414:(20:3)
1408:(20:2)
1402:(18:3)
1396:(18:3)
1390:(18:3)
1384:-18:2)
1374:(18:2)
1368:(18:1)
1362:(14:1)
1343:(20:4)
1337:(20:3)
1331:(18:3)
1325:(18:3)
1319:-18:3)
1309:(18:3)
1303:(16:1)
1297:(14:1)
1278:(24:6)
1272:(24:5)
1266:(22:6)
1260:(22:5)
1254:(20:5)
1248:(20:4)
1242:(20:3)
1236:(18:4)
1230:(18:4)
1224:(18:3)
1218:(16:4)
1212:(16:3)
1206:(14:3)
1200:(14:2)
1194:(14:1)
1188:(12:2)
1182:(12:1)
1176:(10:2)
1170:(10:1)
1107:Geddic
975:Lauric
963:Capric
901:Lipids
824:
790:
749:
708:
698:
659:
649:
600:
577:
569:
530:
439:, and
433:esters
385:verify
382:
302:SMILES
174:C21942
33:Names
1508:trans
1498:Oleic
1382:trans
1317:trans
1164:(8:1)
1145:(C40)
1139:(C39)
1133:(C38)
1127:(C37)
1121:(C36)
1115:(C35)
1109:(C34)
1103:(C33)
1097:(C32)
1091:(C31)
1085:(C30)
1079:(C29)
1073:(C28)
1067:(C27)
1061:(C26)
1055:(C25)
1049:(C24)
1043:(C23)
1037:(C22)
1031:(C21)
1025:(C20)
1019:(C19)
1013:(C18)
1007:(C17)
1001:(C16)
995:(C15)
989:(C14)
983:(C13)
977:(C12)
971:(C11)
965:(C10)
864:Waxes
822:S2CID
810:(PDF)
575:S2CID
437:anion
429:salts
417:sebum
411:is a
267:InChI
125:ChEBI
103:JSmol
1538:Mead
959:(C9)
953:(C8)
947:(C7)
941:(C6)
935:(C5)
929:(C4)
923:(C3)
847:help
788:PMID
747:PMID
706:PMID
684:1861
657:PMID
598:ISBN
567:PMID
528:PMID
210:UNII
165:KEGG
814:doi
778:doi
774:120
737:doi
733:118
696:PMC
688:doi
647:PMC
639:doi
627:197
559:doi
555:211
518:doi
514:124
471:of
236:EPA
189:CID
57:cis
1625::
903::
838::
836:}}
832:{{
820:.
812:.
786:.
772:.
768:.
745:.
731:.
727:.
704:.
694:.
682:.
678:.
655:.
645:.
637:.
625:.
621:.
573:.
565:.
553:.
549:.
526:.
512:.
508:.
435:,
431:,
340:30
334:16
43:(6
1506:(
1380:(
1315:(
893:e
886:t
879:v
849:)
845:(
828:.
816::
794:.
780::
753:.
739::
712:.
690::
663:.
641::
633::
606:.
581:.
561::
534:.
520::
459:.
380:N
346:2
343:O
337:H
331:C
238:)
234:(
105:)
67:)
45:Z
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
