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Margaric acid

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derivatives of margaric acid are found in nature, although rarely. Unsaturation occurs at position 9 or both at 9 and 12 positions of the fatty chain giving heptadecenoic (C17:1) and heptadecadienoic (C17:2) acids, respectively. C17:1 cis-9 (ω-8) is found at trace amounts in
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Margaric acid is rare in animals and vegetables. In the 19th and early 20th centuries, however, the acid was often identified as a significant component of natural fats. Most likely, these were cases of misidentifying a
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Razakov, R. R.; Sadykov, A. S. (July 1986). "Study of complex mixtures of natural substances by the defocusing and dadi methods. VI. Components of the secretion of the pre-anal gland of some poisonous snakes".
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Sánchez-Rodríguez, Lucía; Kranjac, Marina; Marijanović, Zvonimir; Jerković, Igor; Corell, Mireia; Moriana, Alfonso; Carbonell-Barrachina, Ángel A.; Sendra, Esther; Hernández, Francisca (2019-06-06).
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Mason, Robert T.; Gutzke, William H. N. (January 1990). "Sex recognition in the leopard gecko,Eublepharis macularius (Sauria: Gekkonidae) Possible mediation by skin-derived semiochemicals".
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Ayorinde, F.; Wheeler, J. W.; Wemmer, C.; Murtaugh, J. (January 1982). "Volatile components of the occipital gland secretion of the bactrian camel (Camelus bactrianus)".
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Ayorinde, F.; Wheeler, J. W.; Wemmer, C.; Murtaugh, J. (January 1982). "Volatile components of the occipital gland secretion of the bactrian camel (Camelus bactrianus)".
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Margaric acid is also found in the precloacal gland secretions of many reptiles belonging to the order
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InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
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Sin, Yung Wa; Buesching, Christina D.; Burke, Terry; Macdonald, David W. (2012-05-30).
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properties. Margaric acid has been identified in the subcaudal gland secretions of the
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InChI=1/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
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Mass spectrometric investigations of mosquito attraction to human skin emanations /
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Alves, S.P.; Marcelino, C.; Portugal, P.V.; Bessa, R.J.B. (2006-01-01).
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Except where otherwise noted, data are given for materials in their
890: 861: 831: 781: 738: 612: 125: 955:"Occurrence in Butterfat of n-Heptadecanoic Acid (Margaric Acid)" 894: 560: 439: 259: 848:), where it is used for the identification of sexual partners. 169: 542: 1601: 1477: 1125: 1066: 746: 600: 149: 115: 309: 1320: 737:, it occurs as a trace component of the fat and milkfat of 538: 1009: 1478:
Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001).
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R. P. Hansen, F. B. Shorland and N. June Cooke (1957).
1529:] (in Russian). Moskva: Chimia. pp. 116–120. 879: 1480:"Lexicon of lipid nutrition (IUPAC Technical Report)" 534: 464:
227 °C (441 °F; 500 K) 100 mmHg
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Tchiot ili netchet? Zanimatelnye otcherki po chimii
772:For many species, margaric acid plays a role as a 2321: 792:) and in the occipital gland secretions of male 271: 101: 1268: 764:), meaning "pearl(y)", due to its appearance. 608: 1586: 1527:Odd or Even? Entertaining Essays on Chemistry 1435:Journal of the American Oil Chemists' Society 1209: 454:61.3 °C (142.3 °F; 334.4 K) 1593: 1579: 324: 219: 197: 1495: 1446: 1405: 1387: 1338: 1035: 978: 291: 1600: 1518: 1471: 1184: 320: 14: 2322: 1558:"Human Metabolome Database, HMDB02259" 803:Margaric acid is an attractant of the 210: 1574: 352:Key: KEMQGTRYUADPNZ-UHFFFAOYSA-N 177: 157: 1428: 851: 880:Rarity in vegetable and animal fats 362:Key: KEMQGTRYUADPNZ-UHFFFAOYAT 262: 24: 1977:6,9,12,15,18,21-Tetracosahexaenoic 1519:Leenson, Ilia Abramovitch (1987). 25: 2351: 1971:9,12,15,18,21-Tetracosapentaenoic 1550: 1340:10.3168/jds.S0022-0302(06)72081-1 767: 1037:10.1111/j.1574-6941.2012.01396.x 668: 504: 42: 33: 1512: 1422: 1363: 664:(at 25 °C , 100 kPa). 1314: 1272:Chemistry of Natural Compounds 1262: 1203: 1178: 1119: 1060: 1003: 946: 929: 13: 1: 922: 907:List of saturated fatty acids 756:Its name is derived from the 819:) but is a repellent of the 776:- specifically it possesses 749:of margaric acid are called 7: 1212:Journal of Chemical Ecology 1185:Bernier, Ulrich R. (1995). 1128:Journal of Chemical Ecology 1069:Journal of Chemical Ecology 900: 864:fats and some varieties of 713:. Its molecular formula is 10: 2356: 1484:Pure and Applied Chemistry 842:) and the European viper ( 426:270.45 g/mol 2286: 2267: 2248: 2189: 2146: 2051: 1986: 1853: 1612: 1448:10.1007/s11746-012-2071-5 1429:Dowd, Michael K. (2012). 1389:10.3390/molecules24112148 1016:FEMS Microbiology Ecology 658: 618: 485: 480: 391: 371: 336: 85: 67: 55: 50: 41: 32: 2030:7,10,13-Octadecatrienoic 1327:Journal of Dairy Science 912:List of carboxylic acids 551:Precautionary statements 1497:10.1351/pac200173040685 1197:10.5962/bhl.title.49749 2180:7,10,13-Eicosatrienoic 2036:9,12,15-Eicosatrienoic 840:Eublepharis macularius 383:O=C(O)CCCCCCCCCCCCCCCC 821:common house mosquito 813:yellow fever mosquito 836:common leopard gecko 809:Trogoderma granarium 735:odd-chain fatty acid 57:Preferred IUPAC name 1284:1986CNatC..22..392R 1224:1990JCEco..16...27M 1140:1982JCEco...8..177A 1081:1982JCEco...8..177A 1028:2012FEMME..81..648S 971:1957Natur.179...98H 733:. Classified as an 471:Solubility in water 139:Beilstein Reference 29: 2233:8,11-Eicosadienoic 2113:Dihomo-γ-linolenic 2042:β-Eicosatetraenoic 1941:Dihomo-α-linolenic 1826:Heptatriacontanoic 1292:10.1007/bf00579807 1232:10.1007/bf01021265 1148:10.1007/bf00984014 1089:10.1007/bf00984014 874:Thespesia populnea 798:Camelus bactrianus 707:heptadecanoic acid 691:Infobox references 619:Related compounds 70:Heptadecylic acid; 61:Heptadecanoic acid 27: 18:Heptadecanoic acid 2317: 2316: 1838:Nonatriacontanoic 1832:Octatriacontanoic 1536:978-5-518-13939-8 917:Pentadecylic acid 852:Unsaturated forms 709:, is a saturated 699:Chemical compound 697: 696: 644:Related compounds 529:Hazard statements 305:CompTox Dashboard 127:Interactive image 16:(Redirected from 2347: 2288:ω−12 Unsaturated 2269:ω−11 Unsaturated 2250:ω−10 Unsaturated 1953:Eicosapentaenoic 1947:Eicosatetraenoic 1911:Palmitolinolenic 1905:Myristolinolenic 1820:Hexatriacontylic 1595: 1588: 1581: 1572: 1571: 1567: 1565: 1564: 1544: 1540: 1516: 1510: 1509: 1499: 1475: 1469: 1468: 1450: 1441:(9): 1599–1609. 1426: 1420: 1419: 1409: 1391: 1367: 1361: 1360: 1342: 1318: 1312: 1311: 1266: 1260: 1259: 1207: 1201: 1200: 1182: 1176: 1175: 1123: 1117: 1116: 1064: 1058: 1057: 1039: 1007: 1001: 1000: 982: 980:10.1038/179098a0 950: 944: 940:, 13th Edition, 933: 887:eutectic mixture 834:, including the 732: 681: 675: 672: 671: 614: 610: 606: 602: 598: 594: 590: 586: 582: 578: 574: 570: 566: 562: 558: 544: 540: 536: 508: 399:Chemical formula 329: 328: 313: 311: 295: 275: 264: 248:Gmelin Reference 231: 223: 212: 201: 181: 161: 129: 105: 74:Margarinic acid; 46: 37: 30: 26: 21: 2355: 2354: 2350: 2349: 2348: 2346: 2345: 2344: 2320: 2319: 2318: 2313: 2282: 2263: 2244: 2191:ω−9 Unsaturated 2185: 2148:ω−7 Unsaturated 2142: 2107:Dihomo-linoleic 2067:12-Octadecenoic 2061:8-Tetradecenoic 2053:ω−6 Unsaturated 2047: 2002:Palmitovaccenic 1988:ω−5 Unsaturated 1982: 1965:Docosahexaenoic 1899:Myristolinoleic 1893:Myristovaccenic 1855:ω−3 Unsaturated 1849: 1790:Hentriacontylic 1608: 1599: 1562: 1560: 1556: 1553: 1548: 1547: 1537: 1517: 1513: 1476: 1472: 1427: 1423: 1368: 1364: 1319: 1315: 1267: 1263: 1208: 1204: 1183: 1179: 1124: 1120: 1065: 1061: 1008: 1004: 951: 947: 934: 930: 925: 903: 882: 854: 794:Bactrian camels 786:European badger 770: 751:heptadecanoates 730: 726: 722: 718: 714: 700: 693: 688: 687: 686:  ?) 677: 673: 669: 665: 651: 645: 635: 629: 553: 531: 517: 501: 473: 434:White crystals 415: 411: 407: 401: 387: 384: 379: 378: 367: 364: 363: 360: 354: 353: 350: 344: 343: 332: 314: 307: 298: 278: 265: 250: 241: 204: 184: 164: 141: 132: 119: 108: 95: 81: 75: 73: 71: 63: 62: 23: 22: 15: 12: 11: 5: 2353: 2343: 2342: 2340:Semiochemicals 2337: 2335:Alkanoic acids 2332: 2315: 2314: 2312: 2311: 2305: 2299: 2296:4-Hexadecenoic 2292: 2290: 2284: 2283: 2281: 2280: 2273: 2271: 2265: 2264: 2262: 2261: 2254: 2252: 2246: 2245: 2243: 2242: 2236: 2230: 2224: 2218: 2212: 2202: 2195: 2193: 2187: 2186: 2184: 2183: 2177: 2171: 2165: 2159: 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768:Semiochemistry 766: 728: 724: 720: 716: 698: 695: 694: 689: 667: 666: 662:standard state 659: 656: 655: 646: 643: 640: 639: 630: 624: 621: 620: 616: 615: 581:P305+P351+P338 554: 549: 546: 545: 532: 527: 524: 523: 518: 513: 510: 509: 502: 497: 494: 493: 483: 482: 478: 477: 474: 469: 466: 465: 462: 456: 455: 452: 446: 445: 442: 436: 435: 432: 428: 427: 424: 418: 417: 413: 409: 405: 402: 397: 394: 393: 389: 388: 386: 385: 382: 374: 373: 372: 369: 368: 366: 365: 361: 358: 357: 355: 351: 348: 347: 339: 338: 337: 334: 333: 331: 330: 317: 315: 303: 300: 299: 297: 296: 288: 286: 280: 279: 277: 276: 268: 266: 258: 255: 254: 251: 246: 243: 242: 240: 239: 235: 233: 225: 224: 214: 206: 205: 203: 202: 194: 192: 186: 185: 183: 182: 174: 172: 166: 165: 163: 162: 154: 152: 146: 145: 142: 137: 134: 133: 131: 130: 122: 120: 113: 110: 109: 107: 106: 98: 96: 91: 88: 87: 83: 82: 69: 65: 64: 60: 59: 53: 52: 48: 47: 39: 38: 28:Margaric acid 9: 6: 4: 3: 2: 2352: 2341: 2338: 2336: 2333: 2331: 2328: 2327: 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437: 433: 430: 429: 425: 423: 420: 419: 403: 400: 396: 395: 390: 381: 380: 377: 370: 356: 346: 345: 342: 335: 327: 323: 322:DTXSID5021596 319: 318: 316: 306: 302: 301: 294: 290: 289: 287: 285: 282: 281: 274: 270: 269: 267: 261: 257: 256: 252: 249: 245: 244: 237: 236: 234: 232: 227: 226: 222: 218: 215: 213: 211:ECHA InfoCard 208: 207: 200: 196: 195: 193: 191: 188: 187: 180: 179:ChEMBL1172910 176: 175: 173: 171: 168: 167: 160: 156: 155: 153: 151: 148: 147: 143: 140: 136: 135: 128: 124: 123: 121: 117: 112: 111: 104: 100: 99: 97: 94: 90: 89: 84: 79: 78:Lipid numbers 72:Daturic acid; 66: 58: 54: 49: 45: 40: 36: 31: 19: 2308:8-Eicosenoic 2302:Petroselinic 2208: 2082: 2079:Linolelaidic 2017: 1959:Clupanodonic 1917:Palmitidonic 1754:Pentacosylic 1730:Heneicosylic 1705: 1694:Pentadecylic 1561:. Retrieved 1526: 1521: 1514: 1487: 1483: 1473: 1438: 1434: 1424: 1382:(11): 2148. 1379: 1375: 1365: 1330: 1326: 1316: 1275: 1271: 1264: 1218:(1): 27–36. 1215: 1211: 1205: 1187: 1180: 1131: 1127: 1121: 1072: 1068: 1062: 1019: 1015: 1005: 962: 958: 948: 941: 935: 931: 883: 873: 855: 845:Vipera berus 843: 839: 829: 824: 816: 808: 802: 797: 789: 771: 761: 755: 750: 706: 702: 701: 653:Heptadecanal 649:Heptadecanol 637:Stearic acid 520: 487: 86:Identifiers 68:Other names 2330:Fatty acids 2156:Palmitoleic 2125:Arachidonic 2089:γ-Linolenic 1996:Myristoleic 1935:α-Parinaric 1929:Stearidonic 1923:α-Linolenic 1875:Decadienoic 1814:Ceroplastic 1778:Nonacosylic 1718:Nonadecylic 1606:fatty acids 937:Merck Index 870:Portia tree 857:Unsaturated 790:Meles meles 627:fatty acids 515:Signal word 444:0.853 g/cm 431:Appearance 392:Properties 217:100.007.298 159:CHEBI:32365 2324:Categories 1766:Carboceric 1748:Lignoceric 1742:Tricosylic 1682:Tridecylic 1658:Pelargonic 1563:2008-11-08 965:(98): 98. 923:References 866:olive oils 811:) and the 778:pheromonic 762:márgar(on) 760:μάργαρος ( 711:fatty acid 499:Pictograms 476:insoluble 422:Molar mass 293:V987Y9OZ8L 190:ChemSpider 114:3D model ( 93:CAS Number 2174:Paullinic 2119:Sciadonic 2101:Pinolenic 1881:Lauroleic 1796:Lacceroic 1724:Arachidic 1670:Undecylic 1622:Propionic 1614:Saturated 1457:1558-9331 1398:1420-3049 1376:Molecules 1349:0022-0302 1300:0009-3130 1240:0098-0331 1156:0098-0331 1097:0098-0331 1046:0168-6496 782:allomonic 739:ruminants 605:P403+P233 597:P337+P313 593:P332+P313 577:P304+P340 573:P302+P352 490:labelling 238:208-027-1 230:EC Number 2277:Gadoleic 2258:Sapienic 2227:Nervonic 2162:Vaccenic 2095:Calendic 2073:Linoleic 1869:Decenoic 1863:Octenoic 1784:Melissic 1772:Montanic 1706:Margaric 1700:Palmitic 1688:Myristic 1652:Caprylic 1646:Enanthic 1506:84492006 1465:84820785 1416:31174411 1357:16357280 1308:24684170 1256:28887051 1248:24264893 1172:21202532 1164:24414593 1113:21202532 1105:24414593 1054:22530962 989:13400103 901:See also 891:palmitic 862:ruminant 832:squamata 625:Related 481:Hazards 144:1781004 103:506-12-7 2215:Gondoic 2205:Elaidic 2168:Rumenic 2131:Adrenic 2024:Punicic 1802:Psyllic 1760:Cerotic 1736:Behenic 1712:Stearic 1640:Caproic 1634:Valeric 1628:Butyric 1407:6600446 1280:Bibcode 1220:Bibcode 1136:Bibcode 1077:Bibcode 1024:Bibcode 997:4144443 967:Bibcode 897:acids. 895:stearic 684:what is 682: ( 521:Warning 440:Density 416: 260:PubChem 253:253195 2310:(20:1) 2304:(18:1) 2298:(16:1) 2279:(20:1) 2260:(16:1) 2241:(20:3) 2235:(20:2) 2229:(24:1) 2223:(22:1) 2221:Erucic 2217:(20:1) 2211:-18:1) 2201:(18:1) 2182:(20:3) 2176:(20:1) 2170:(18:2) 2164:(18:1) 2158:(16:1) 2139:(22:5) 2137:Osbond 2133:(22:4) 2127:(20:4) 2121:(20:3) 2115:(20:3) 2109:(20:2) 2103:(18:3) 2097:(18:3) 2091:(18:3) 2085:-18:2) 2075:(18:2) 2069:(18:1) 2063:(14:1) 2044:(20:4) 2038:(20:3) 2032:(18:3) 2026:(18:3) 2020:-18:3) 2010:(18:3) 2004:(16:1) 1998:(14:1) 1979:(24:6) 1973:(24:5) 1967:(22:6) 1961:(22:5) 1955:(20:5) 1949:(20:4) 1943:(20:3) 1937:(18:4) 1931:(18:4) 1925:(18:3) 1919:(16:4) 1913:(16:3) 1907:(14:3) 1901:(14:2) 1895:(14:1) 1889:(12:2) 1883:(12:1) 1877:(10:2) 1871:(10:1) 1808:Geddic 1676:Lauric 1664:Capric 1602:Lipids 1533:  1504:  1463:  1455:  1414:  1404:  1396:  1355:  1347:  1306:  1298:  1254:  1246:  1238:  1170:  1162:  1154:  1111:  1103:  1095:  1052:  1044:  995:  987:  959:Nature 747:esters 679:verify 676:  376:SMILES 170:ChEMBL 76:17:0 ( 51:Names 2209:trans 2199:Oleic 2083:trans 2018:trans 1865:(8:1) 1846:(C40) 1840:(C39) 1834:(C38) 1828:(C37) 1822:(C36) 1816:(C35) 1810:(C34) 1804:(C33) 1798:(C32) 1792:(C31) 1786:(C30) 1780:(C29) 1774:(C28) 1768:(C27) 1762:(C26) 1756:(C25) 1750:(C24) 1744:(C23) 1738:(C22) 1732:(C21) 1726:(C20) 1720:(C19) 1714:(C18) 1708:(C17) 1702:(C16) 1696:(C15) 1690:(C14) 1684:(C13) 1678:(C12) 1672:(C11) 1666:(C10) 1525:[ 1502:S2CID 1461:S2CID 1304:S2CID 1252:S2CID 1168:S2CID 1109:S2CID 993:S2CID 743:Salts 705:, or 341:InChI 273:10465 199:10033 150:ChEBI 116:JSmol 2239:Mead 1660:(C9) 1654:(C8) 1648:(C7) 1642:(C6) 1636:(C5) 1630:(C4) 1624:(C3) 1531:ISBN 1453:ISSN 1412:PMID 1394:ISSN 1353:PMID 1345:ISSN 1296:ISSN 1244:PMID 1236:ISSN 1160:PMID 1152:ISSN 1101:PMID 1093:ISSN 1050:PMID 1042:ISSN 985:PMID 942:5775 893:and 889:of 780:and 745:and 613:P501 609:P405 601:P362 589:P321 585:P312 569:P280 565:P271 561:P264 557:P261 543:H335 539:H319 535:H315 284:UNII 1492:doi 1443:doi 1402:PMC 1384:doi 1335:doi 1288:doi 1228:doi 1193:doi 1191:. 1144:doi 1085:doi 1032:doi 975:doi 963:179 876:). 827:). 719:(CH 488:GHS 310:EPA 263:CID 2326:: 1604:: 1500:. 1488:73 1486:. 1482:. 1459:. 1451:. 1439:89 1437:. 1433:. 1410:. 1400:. 1392:. 1380:24 1378:. 1374:. 1351:. 1343:. 1331:89 1329:. 1325:. 1302:. 1294:. 1286:. 1276:22 1274:. 1250:. 1242:. 1234:. 1226:. 1216:16 1214:. 1166:. 1158:. 1150:. 1142:. 1130:. 1107:. 1099:. 1091:. 1083:. 1071:. 1048:. 1040:. 1030:. 1020:81 1018:. 1014:. 991:. 983:. 973:. 961:. 957:. 753:. 741:. 727:CO 725:15 715:CH 611:, 607:, 603:, 599:, 595:, 591:, 587:, 583:, 579:, 575:, 571:, 567:, 563:, 559:, 541:, 537:, 492:: 410:34 406:17 2207:( 2081:( 2016:( 1594:e 1587:t 1580:v 1566:. 1539:. 1508:. 1494:: 1467:. 1445:: 1418:. 1386:: 1359:. 1337:: 1310:. 1290:: 1282:: 1258:. 1230:: 1222:: 1199:. 1195:: 1174:. 1146:: 1138:: 1132:8 1115:. 1087:: 1079:: 1073:8 1056:. 1034:: 1026:: 999:. 977:: 969:: 872:( 838:( 823:( 815:( 807:( 796:( 788:( 731:H 729:2 723:) 721:2 717:3 674:Y 414:2 412:O 408:H 404:C 312:) 308:( 118:) 80:) 20:)

Index

Heptadecanoic acid
Heptadecanoic acid

Preferred IUPAC name
Lipid numbers
CAS Number
506-12-7
JSmol
Interactive image
Beilstein Reference
ChEBI
CHEBI:32365
ChEMBL
ChEMBL1172910
ChemSpider
10033
ECHA InfoCard
100.007.298
Edit this at Wikidata
EC Number
Gmelin Reference
PubChem
10465
UNII
V987Y9OZ8L
CompTox Dashboard
DTXSID5021596
Edit this at Wikidata
InChI
SMILES

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