1129:
370:
273:
55:
46:
509:
1213:. Consumers are increasingly avoiding products that contain trans fats, and governments have begun to ban trans fats in food products. These regulations and market pressures have spurred the development of soybeans low in α-linolenic acid. These new soybean varieties yield a more stable oil that often do not require hydrogenation for many applications.
1258:, Germany, working independently, as cited in J. W. McCutcheon's synthesis in 1942, and referred to in Green and Hilditch's 1930s survey. It was first artificially synthesized in 1995 from C6 homologating agents. A Wittig reaction of the phosphonium salt of triphenylphosphonium bromide with methyl 9-oxononanoate, followed by
756:
consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra. Some studies state that ALA remains stable during processing and cooking. However, other studies state
1249:
In 1887, linolenic acid was discovered and named by the
Austrian chemist Karl Hazura of the Imperial Technical Institute at Vienna (although he did not separate its isomers). α-Linolenic acid was first isolated in pure form in 1909 by Ernst Erdmann and F. Bedford of the
1178:−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA. Conversion of ALA to DHA is higher in women than in men.
1330:
Loreau O, Maret A, Poullain D, Chardigny JM, Sébédio JL, Beaufrère B, Noël JP (2000). "Large-scale preparation of (9Z,12E)--octadeca-9,12-dienoic acid, (9Z,12Z,15E)--octadeca-9,12,15-trienoic acid and their 1-C all-cis isomers".
1241:. A 2021 review found that ALA intake is associated with a reduced risk of mortality from all causes, cardiovascular disease, and coronary heart disease but a slightly higher risk of cancer mortality.
2950:
2944:
2128:"Research Dietary intake and biomarkers of alpha linolenic acid and risk of all cause, cardiovascular, and cancer mortality: systematic review and dose-response meta-analysis of cohort studies"
1508:
2890:
3015:
3003:
2884:
2878:
2914:
3153:
3009:
2872:
2330:"Wir bezeichnen diese in Leinöl vorhandene Linolensäure, welche das feste Hexabromid liefert, zum Unterschied von einer später zu erwähnenden Isomeren als α-Linolensäure."
1629:"Physicochemical Properties, Fatty Acid Composition, Volatile Compounds of Blueberries, Cranberries, Raspberries, and Cuckooflower Seeds Obtained Using Sonication Method"
3206:
1469:
Manthey FA, Lee RE, Hall CA (2002). "Processing and cooking effects on lipid content and stability of alpha-linolenic acid in spaghetti containing ground flaxseed".
1457:
2860:
2811:
2805:
765:
with transition metal catalysts. Some ALA may also oxidize at baking temperatures. ALA percentages in the table below refer to the oils extracted from each item.
2866:
2357:
2315:
2216:
3080:
3040:
3034:
2975:
2848:
3269:
3261:
3242:
3223:
2817:
2961:
3281:
2854:
2332:(We designate this linolenic acid, which the solid hexabromide provides, as α-linolenic acid in order to distinguish from an isomer mentioned later.)
522:
2842:
2836:
1504:
2104:
1853:
1691:
1943:
1627:
Bederska-Łojewska D, Pieszka M, Marzec A, Rudzińska M, Grygier A, Siger A, Cieślik-Boczula K, Orczewska-Dudek S, Migdał W (December 2021).
1251:
419:
170:
163:
1379:
1879:
1713:
2069:"Effects of α-linolenic acid intake on blood lipid profiles：a systematic review and meta-analysis of randomized controlled trials"
1458:
https://www.researchgate.net/publication/230822408_13-C_NMR_studies_of_lipid_fatty_acyl_chains_of_chloroplast_membranes?ev=prf_pub
1206:
are the largest source of edible oils in the U.S., and, as of a 2007 study, 40% of soy oil production was partially hydrogenated.
605:
517:
393:
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
1912:
403:
InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
2566:
291:
17:
1571:"Camelina (Camelina sativa (L.) Crantz) as Feedstuffs in Meat Type Poultry Diet: A Source of Protein and n-3 Fatty Acids"
3303:
2165:
2337:
2295:
2188:
1128:
384:
529:
633:. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the
1225:
and a reduced risk of fatal coronary heart disease. Dietary ALA intake can improve lipid profiles by decreasing
3313:
2403:
3318:
327:
268:
1296:
348:
1255:
700:
produces oleic acid. Similarly saturating one of linolenic acid's double bonds produces linoleic acid.
3333:
638:
210:
3086:
1547:
2559:
616:-9,12,15-octadecatrienoic acid. In physiological literature, it is listed by its lipid number, 18:3 (
2068:
2067:
Hao Y, Bin Q, Min J, Wei L, Xiao-fei G, Na L, Zhi-xiang X, Fang-ling D, Tongcheng X, Duo L (2020).
1971:"Impact of α-Linolenic Acid, the Vegetable ω-3 Fatty Acid, on Cardiovascular Disease and Cognition"
1234:
365:
1406:"Growth temperature effects on thylakoid membrane lipid and protein content of pea chloroplasts 1"
3328:
3323:
2799:
1784:
1679:
1569:
Juodka R, Nainiené R, Juškiené V, Juška R, Leikus R, Kadžiené G, Stankevičiené D (January 2022).
1238:
709:
626:
1947:
1821:"Conversion of alpha-linolenic acid to longer-chain polyunsaturated fatty acids in human adults"
1820:
1372:
1222:
1970:
3110:
3104:
2932:
2926:
2920:
2793:
1163:
1159:
1155:
230:
2987:
2981:
2020:"α-Linolenic acid and risk of cardiovascular disease: a systematic review and meta-analysis"
3308:
3062:
2938:
2763:
2552:
1291:
1281:
1171:
649:
578:
336:
67:
1452:
YashRoy R.C. (1987) 13-C NMR studies of lipid fatty acyl chains of chloroplast membranes.
8:
2513:
139:
129:
2908:
1886:
1717:
369:
272:
190:
3188:
3164:
3121:
3026:
2828:
2530:
2480:
2454:
2208:
2152:
2096:
2044:
2019:
1995:
1759:
1732:
1655:
1628:
1597:
1570:
1430:
1405:
1305:
657:
571:
1344:
1139:α-Linolenic acid can be obtained by humans only through their diets. Humans lack the
3275:
3052:
2727:
2703:
2667:
2534:
2511:)-1,4-dienic units with a new C6 homologating agent: synthesis of α-linolenic acid".
2485:
2431:
2212:
2157:
2100:
2088:
2049:
2000:
1920:
1845:
1801:
1797:
1764:
1660:
1602:
1486:
1435:
1348:
1230:
316:
3129:
3098:
2969:
2902:
2787:
2751:
2691:
2522:
2475:
2467:
2395:
2349:
2307:
2200:
2147:
2139:
2080:
2039:
2031:
1990:
1982:
1835:
1793:
1754:
1744:
1650:
1640:
1592:
1582:
1478:
1425:
1417:
1340:
1186:
Compared to many other oils, α-linolenic acid is more susceptible to oxidation. It
1151:
715:
447:
2399:
2084:
714:
Seed oils are the richest sources of α-linolenic acid, notably those of hempseed,
2739:
2721:
2715:
2655:
2631:
1191:
1187:
1154:, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (
889:
621:
2426:
3147:
3092:
3074:
2769:
2697:
2643:
2595:
1986:
1310:
1259:
677:
556:
500:
30:
2353:
2311:
1944:"ADM to process Monsanto's Vistive low linolenic soybeans at Indiana facility"
1645:
3297:
3250:
3231:
3200:
3135:
3068:
3046:
2757:
2745:
2679:
2673:
2661:
2625:
2619:
2587:
1403:
1276:
1195:
969:
929:
748:
697:
598:
261:
2127:
2035:
3178:
3141:
2997:
2775:
2733:
2709:
2685:
2613:
2607:
2601:
2489:
2161:
2092:
2053:
2004:
1849:
1805:
1768:
1749:
1664:
1606:
1490:
1439:
1352:
1226:
1167:
1144:
1840:
3194:
2781:
2649:
2637:
2459:
1199:
1092:
753:
727:
719:
645:
630:
2526:
2281:
the name "linolenic acid".) Linolenic acid is discussed on pp. 265-268.
1587:
1421:
250:
54:
3172:
2579:
2204:
1687:
1626:
1286:
1271:
1140:
1052:
762:
693:
475:
281:
221:
2544:
2471:
2143:
1482:
3212:
1210:
1009:
989:
949:
909:
808:
788:
743:
590:
2383:
1194:
of α-linolenic acid is one reason why producers choose to partially
499:
Except where otherwise noted, data are given for materials in their
2328:
On p. 1329 they distinguish one of the isomers of linolenic acid:
2126:
Naghshi S, Aune D, Beyene J, Mobarak S, Asadi M, Sadeghi O (2021).
1782:
Shiels M. Innis (2007). "Fatty acids and early human development".
1072:
1014:
869:
731:
723:
582:
241:
169:
162:
1203:
829:
758:
739:
488:
303:
1968:
1880:"Metabolism in plants to produce healthier food oils (slide #4)"
735:
586:
201:
45:
1404:
Chapman, David J., De-Felice, John, Barber, James (May 1983).
2575:
1730:
181:
152:
1329:
353:
29:
This article is about α-Linolenic acid. For other uses, see
1910:
1568:
1543:
1132:
1032:
849:
685:
594:
567:
2018:
Pan A, Chen M, Chowdhury R, et al. (December 2012).
2125:
1733:"Are all n-3 polyunsaturated fatty acids created equal?"
1147:
into A-linoleic acid or other unsaturated fatty acids.
1969:
Sala-Vila A, Fleming J, Kris-Etherton P, Ros E (2022).
1716:. University of Maryland Medical Center. Archived from
2503:
Sandri, J., Viala, J. (1995). "Direct preparation of (
1505:"OXIDATIVE STABILITY OF FLAXSEED LIPIDS DURING BAKING"
2386:[ knowledge of linolenic acid and flax oil].
2370:
The structure of α-linolenic acid appears on p. 1343.
757:
that ALA might not be suitable for baking as it will
2455:"The identification of linoleic and linolenic acids"
2298:[On linolenic acid contained in flax oil].
2502:
2335:
1622:
1620:
1618:
1616:
1221:ALA consumption is associated with a lower risk of
1209:Hydrogenation of ALA-containing fats can introduce
290:
2269:I suggest the name "linolic acid"; for the acid C
2243:schlage ich den Namen Linolsäure, für die Säure C
581:. ALA is found in many seeds and oils, including
3295:
2424:
2017:
1613:
1544:"Seed Oil Fatty Acids – SOFA Database Retrieval"
315:
2384:"Zur Kenntnis der Linolensäure und des Leinöls"
1781:
696:" because saturating an omega-6 double bond of
138:
117:)-9,12,15-Octadecatrienoic acid; Industrene 120
2342:Berichte der Deutschen Chemischen Gesellschaft
2300:Berichte der Deutschen Chemischen Gesellschaft
2293:
2073:Critical Reviews in Food Science and Nutrition
1468:
1181:
2560:
2452:
1454:Indian Journal of Biochemistry and Biophysics
742:. α-Linolenic acid is also obtained from the
2296:"Über die im Leinöl enthaltene Linolensäure"
2066:
1818:
1370:
2381:
1150:Dietary α-linolenic acid is metabolized to
2567:
2553:
2191:[On drying oily acids 4th paper].
1198:oils containing α-linolenic acid, such as
368:
271:
229:
2479:
2189:"Über trocknende Ölsäuren IV. Abhandlung"
2151:
2043:
1994:
1839:
1758:
1748:
1654:
1644:
1596:
1586:
1429:
335:
1877:
1731:Breanne M Anderson, David WL Ma (2009).
1538:
1536:
1534:
1532:
1530:
1528:
1526:
1127:
710:Vegetable oil § Composition of fats
656:−6) fatty acid (i.e., a polyunsaturated
2574:
2340:[Structure of linolenic acid].
1366:
1364:
1362:
1254:, Germany, and by Adolf Rollett of the
1168:6,9,12,15,18,21-tetracosahexaenoic acid
364:
249:
14:
3296:
2336:Erdmann E, Bedford F, Raspe F (1909).
2186:
1871:
1694:from the original on 22 September 2006
1684:Perspectives on new crops and new uses
262:
2548:
2388:Zeitschrift für physiologische Chemie
2168:from the original on 14 December 2021
2107:from the original on 14 December 2021
1913:"Ban on trans fat could benefit Iowa"
1680:"Sea buckthorn: New crop opportunity"
1562:
1523:
1385:from the original on 12 February 2006
1135:is a rich source of α-linolenic acid.
396:Key: DTOSIQBPPRVQHS-PDBXOOCHSA-N
209:
189:
2360:from the original on 1 February 2021
2318:from the original on 26 January 2021
2229:Linolenic acid is named on p. 265:
2219:from the original on 18 January 2021
1941:
1828:Reproduction, Nutrition, Development
1550:from the original on 9 November 2018
1511:from the original on 16 October 2015
1359:
761:with itself, a feature exploited in
1911:Fitzgerald, Anne, Brasher, Philip.
1859:from the original on 15 August 2017
676:, which itself is derived from the
406:Key: DTOSIQBPPRVQHS-PDBXOOCHBH
306:
24:
2951:6,9,12,15,18,21-Tetracosahexaenoic
2406:from the original on 18 March 2020
1677:
1671:
1373:"IUPAC Lexicon of Lipid Nutrition"
703:
624:with an 18-carbon chain and three
105:-9,12,15-Octadecatrienoic acid; (9
25:
3345:
2945:9,12,15,18,21-Tetracosapentaenoic
644:−3 (omega-3) fatty acid. It is a
637:end. Thus, α-linolenic acid is a
1917:Truth About Trade and Technology
1798:10.1016/j.earlhumdev.2007.09.004
1252:University of Halle an der Saale
1143:enzymes required for processing
672:is an irregular derivation from
507:
459:
432:CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
427:O=C(O)CCCCCCC\C=C/C\C=C/C\C=C/CC
84:)-Octadeca-9,12,15-trienoic acid
53:
44:
2496:
2446:
2418:
2375:
2338:"Konstitution der Linolensäure"
2284:
2180:
2119:
2060:
2011:
1962:
1935:
1904:
1812:
1775:
1724:
1706:
1333:Chemistry and Physics of Lipids
1057:English walnut / Persian walnut
503:(at 25 °C , 100 kPa).
2453:Green TG, Hilditch TP (1935).
1497:
1462:
1446:
1397:
1323:
465:
453:
13:
1:
2400:10.1515/bchm2.1909.62.5-6.422
2294:Erdmann E, Bedford F (1909).
2085:10.1080/10408398.2020.1790496
1819:Burdge GC, Calder PC (2005).
1345:10.1016/S0009-3084(00)00137-7
1316:
1123:
2255:den Namen Linolensäure vor."
1737:Lipids in Health and Disease
1174:). Because the efficacy of
1166:, tetracosapentaenoic acid,
663:
7:
1265:
1262:, completed the synthesis.
1182:Stability and hydrogenation
10:
3350:
2441:, vol. 3, p. 351
1244:
707:
660:with three double bonds).
93:ALA; LNA; Linolenic acid;
28:
3260:
3241:
3222:
3163:
3120:
3025:
2960:
2827:
2586:
2425:J. W. McCutcheon (1955).
2354:10.1002/cber.190904201218
2312:10.1002/cber.190904201217
1646:10.3390/molecules26247446
1216:
1114:
1111:
692:means "of or relating to
497:
440:
415:
380:
122:
90:
66:
61:
52:
43:
3004:7,10,13-Octadecatrienoic
1987:10.1093/advances/nmac016
1456:vol. 24(6), pp. 177–178.
1235:high-density lipoprotein
3304:5α-Reductase inhibitors
2036:10.3945/ajcn.112.044040
1785:Early Human Development
1239:low-density lipoprotein
978:Hippophae rhamnoides L.
3154:7,10,13-Eicosatrienoic
3010:9,12,15-Eicosatrienoic
2193:Monatshefte für Chemie
1750:10.1186/1476-511X-8-33
1223:cardiovascular disease
1136:
3314:Essential fatty acids
2026:(Systematic review).
1975:Advances in Nutrition
1714:"Omega-3 fatty acids"
1371:Beare-Rogers (2001).
1192:Oxidative instability
1190:more quickly in air.
1164:docosapentaenoic acid
1160:eicosapentaenoic acid
1156:eicosatetraenoic acid
1131:
958:Vaccinium macrocarpon
878:Vaccinium vitis-idaea
2382:Rollett, A. (1909).
1923:on 27 September 2007
1892:on 29 September 2006
1720:on 27 December 2009.
1690:. pp. 335–337.
1292:Essential fatty acid
1282:gamma-Linolenic acid
1172:docosahexaenoic acid
752:(pea leaves). Plant
650:gamma-linolenic acid
579:essential fatty acid
562:meaning "first" and
68:Preferred IUPAC name
18:Alpha-Linolenic acid
3319:Essential nutrients
2527:10.1055/s-1995-3906
1950:on 11 December 2006
1841:10.1051/rnd:2005047
1588:10.3390/ani12030295
1471:J. Agric. Food Chem
1422:10.1104/pp.72.1.225
1020:Vaccinium myrtillus
938:Cardamine pratensis
858:Linum usitatissimum
818:Actinidia chinensis
744:thylakoid membranes
483: g·mol
40:
3207:8,11-Eicosadienoic
3087:Dihomo-γ-linolenic
3016:β-Eicosatetraenoic
2915:Dihomo-α-linolenic
2800:Heptatriacontanoic
2205:10.1007/BF01510049
2024:Am. J. Clin. Nutr.
1686:. Alexandria, VA:
1306:Essential nutrient
1256:Universität Berlin
1137:
954:American cranberry
918:Portulaca oleracea
838:Perilla frutescens
814:Chinese gooseberry
658:omega-6 fatty acid
597:, and many common
530:Infobox references
38:
3334:Insect pheromones
3291:
3290:
2812:Nonatriacontanoic
2806:Octatriacontanoic
2472:10.1042/bj0291552
2439:Collected Volumes
2432:Organic Syntheses
2187:Hazura K (1887).
2144:10.1136/bmj.n2213
2079:(17): 2894–2910.
1483:10.1021/jf011147s
1231:total cholesterol
1121:
1120:
1117:
746:in the leaves of
544:, also known as
538:Chemical compound
536:
535:
349:CompTox Dashboard
171:Interactive image
164:Interactive image
39:α-Linolenic acid
16:(Redirected from
3341:
3262:ω−12 Unsaturated
3243:ω−11 Unsaturated
3224:ω−10 Unsaturated
2927:Eicosapentaenoic
2921:Eicosatetraenoic
2885:Palmitolinolenic
2879:Myristolinolenic
2794:Hexatriacontylic
2569:
2562:
2555:
2546:
2545:
2539:
2538:
2500:
2494:
2493:
2483:
2450:
2444:
2442:
2435:
2427:"Linolenic acid"
2422:
2416:
2415:
2413:
2411:
2394:(5–6): 422–431.
2379:
2373:
2369:
2367:
2365:
2327:
2325:
2323:
2288:
2282:
2231:"Für die Säure C
2228:
2226:
2224:
2184:
2178:
2177:
2175:
2173:
2155:
2123:
2117:
2116:
2114:
2112:
2064:
2058:
2057:
2047:
2015:
2009:
2008:
1998:
1981:(5): 1584–1602.
1966:
1960:
1959:
1957:
1955:
1946:. Archived from
1939:
1933:
1932:
1930:
1928:
1919:. Archived from
1908:
1902:
1901:
1899:
1897:
1891:
1885:. Archived from
1884:
1875:
1869:
1868:
1866:
1864:
1858:
1843:
1825:
1816:
1810:
1809:
1779:
1773:
1772:
1762:
1752:
1728:
1722:
1721:
1710:
1704:
1703:
1701:
1699:
1675:
1669:
1668:
1658:
1648:
1624:
1611:
1610:
1600:
1590:
1566:
1560:
1559:
1557:
1555:
1540:
1521:
1520:
1518:
1516:
1501:
1495:
1494:
1466:
1460:
1450:
1444:
1443:
1433:
1401:
1395:
1394:
1392:
1390:
1384:
1377:
1368:
1357:
1356:
1327:
1152:stearidonic acid
1115:
797:Salvia hispanica
768:
767:
652:(GLA), an 18:3 (
604:In terms of its
542:α-Linolenic acid
520:
514:
511:
510:
482:
467:
461:
455:
448:Chemical formula
373:
372:
357:
355:
339:
319:
308:
294:
275:
264:
253:
233:
213:
193:
173:
166:
142:
57:
48:
41:
37:
21:
3349:
3348:
3344:
3343:
3342:
3340:
3339:
3338:
3294:
3293:
3292:
3287:
3256:
3237:
3218:
3165:ω−9 Unsaturated
3159:
3122:ω−7 Unsaturated
3116:
3081:Dihomo-linoleic
3041:12-Octadecenoic
3035:8-Tetradecenoic
3027:ω−6 Unsaturated
3021:
2976:Palmitovaccenic
2962:ω−5 Unsaturated
2956:
2939:Docosahexaenoic
2873:Myristolinoleic
2867:Myristovaccenic
2829:ω−3 Unsaturated
2823:
2764:Hentriacontylic
2582:
2573:
2543:
2542:
2501:
2497:
2451:
2447:
2437:
2423:
2419:
2409:
2407:
2380:
2376:
2363:
2361:
2321:
2319:
2289:
2285:
2280:
2276:
2272:
2268:
2264:
2260:
2257:(For the acid C
2254:
2250:
2246:
2242:
2238:
2234:
2222:
2220:
2185:
2181:
2171:
2169:
2124:
2120:
2110:
2108:
2065:
2061:
2016:
2012:
1967:
1963:
1953:
1951:
1940:
1936:
1926:
1924:
1909:
1905:
1895:
1893:
1889:
1882:
1876:
1872:
1862:
1860:
1856:
1823:
1817:
1813:
1792:(12): 761–766.
1780:
1776:
1729:
1725:
1712:
1711:
1707:
1697:
1695:
1676:
1672:
1639:(24). Table 2.
1625:
1614:
1567:
1563:
1553:
1551:
1542:
1541:
1524:
1514:
1512:
1503:
1502:
1498:
1467:
1463:
1451:
1447:
1402:
1398:
1388:
1386:
1382:
1375:
1369:
1360:
1328:
1324:
1319:
1268:
1247:
1219:
1184:
1126:
1041:Cannabis sativa
898:Camelina sativa
712:
706:
704:Dietary sources
666:
639:polyunsaturated
622:carboxylic acid
549:-linolenic acid
539:
532:
527:
526:
525: ?)
516:
512:
508:
504:
480:
470:
464:
458:
450:
436:
433:
428:
423:
422:
411:
408:
407:
404:
398:
397:
394:
388:
387:
376:
358:
351:
342:
322:
309:
297:
284:
256:
236:
216:
196:
176:
156:
145:
132:
118:
86:
85:
34:
23:
22:
15:
12:
11:
5:
3347:
3337:
3336:
3331:
3329:Semiochemicals
3326:
3324:Alkenoic acids
3321:
3316:
3311:
3306:
3289:
3288:
3286:
3285:
3279:
3273:
3270:4-Hexadecenoic
3266:
3264:
3258:
3257:
3255:
3254:
3247:
3245:
3239:
3238:
3236:
3235:
3228:
3226:
3220:
3219:
3217:
3216:
3210:
3204:
3198:
3192:
3186:
3176:
3169:
3167:
3161:
3160:
3158:
3157:
3151:
3145:
3139:
3133:
3126:
3124:
3118:
3117:
3115:
3114:
3108:
3102:
3096:
3090:
3084:
3078:
3072:
3066:
3060:
3050:
3044:
3038:
3031:
3029:
3023:
3022:
3020:
3019:
3013:
3007:
3001:
2995:
2985:
2979:
2973:
2966:
2964:
2958:
2957:
2955:
2954:
2948:
2942:
2936:
2930:
2924:
2918:
2912:
2906:
2900:
2894:
2888:
2882:
2876:
2870:
2864:
2858:
2852:
2846:
2840:
2833:
2831:
2825:
2824:
2822:
2821:
2818:Tetracontanoic
2815:
2809:
2803:
2797:
2791:
2785:
2779:
2773:
2767:
2761:
2755:
2749:
2743:
2737:
2731:
2725:
2719:
2713:
2707:
2701:
2695:
2689:
2683:
2677:
2671:
2665:
2659:
2653:
2647:
2641:
2635:
2629:
2623:
2617:
2611:
2605:
2599:
2592:
2590:
2584:
2583:
2572:
2571:
2564:
2557:
2549:
2541:
2540:
2521:(3): 271–275.
2495:
2466:(7): 1552–63.
2445:
2417:
2374:
2372:
2371:
2333:
2283:
2278:
2274:
2270:
2266:
2262:
2258:
2252:
2248:
2244:
2240:
2236:
2232:
2179:
2118:
2059:
2030:(6): 1262–73.
2010:
1961:
1934:
1903:
1878:Kinney, Tony.
1870:
1834:(5): 581–597.
1811:
1774:
1723:
1705:
1678:Li TS (1999).
1670:
1612:
1581:(3). Table 3.
1561:
1522:
1496:
1477:(6): 1668–71.
1461:
1445:
1416:(1): 225–228.
1396:
1358:
1321:
1320:
1318:
1315:
1314:
1313:
1311:Wheat germ oil
1308:
1303:
1301:−3 fatty acids
1294:
1289:
1284:
1279:
1274:
1267:
1264:
1260:saponification
1246:
1243:
1218:
1215:
1188:becomes rancid
1183:
1180:
1125:
1122:
1119:
1118:
1113:
1109:
1108:
1106:
1103:
1098:
1095:
1089:
1088:
1086:
1083:
1081:Brassica napus
1078:
1075:
1069:
1068:
1066:
1063:
1058:
1055:
1049:
1048:
1046:
1043:
1038:
1035:
1029:
1028:
1026:
1023:
1017:
1012:
1006:
1005:
1003:
1000:
995:
992:
986:
985:
983:
980:
975:
972:
966:
965:
963:
960:
955:
952:
946:
945:
943:
940:
935:
932:
926:
925:
923:
920:
915:
912:
906:
905:
903:
900:
895:
892:
886:
885:
883:
880:
875:
872:
866:
865:
863:
860:
855:
852:
846:
845:
843:
840:
835:
832:
826:
825:
823:
820:
815:
812:
805:
804:
802:
799:
794:
791:
785:
784:
781:
778:
775:
774:Alternate name
772:
705:
702:
665:
662:
608:, it is named
599:vegetable oils
577:, or omega-3,
537:
534:
533:
528:
506:
505:
501:standard state
498:
495:
494:
491:
485:
484:
478:
472:
471:
468:
462:
456:
451:
446:
443:
442:
438:
437:
435:
434:
431:
429:
426:
418:
417:
416:
413:
412:
410:
409:
405:
402:
401:
399:
395:
392:
391:
383:
382:
381:
378:
377:
375:
374:
361:
359:
347:
344:
343:
341:
340:
332:
330:
324:
323:
321:
320:
312:
310:
302:
299:
298:
296:
295:
287:
285:
280:
277:
276:
266:
258:
257:
255:
254:
246:
244:
238:
237:
235:
234:
226:
224:
218:
217:
215:
214:
206:
204:
198:
197:
195:
194:
186:
184:
178:
177:
175:
174:
167:
159:
157:
150:
147:
146:
144:
143:
135:
133:
128:
125:
124:
120:
119:
92:
88:
87:
71:
70:
64:
63:
59:
58:
50:
49:
31:Linolenic acid
9:
6:
4:
3:
2:
3346:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3301:
3299:
3283:
3280:
3277:
3274:
3271:
3268:
3267:
3265:
3263:
3259:
3252:
3249:
3248:
3246:
3244:
3240:
3233:
3230:
3229:
3227:
3225:
3221:
3214:
3211:
3208:
3205:
3202:
3199:
3196:
3193:
3190:
3187:
3184:
3180:
3177:
3174:
3171:
3170:
3168:
3166:
3162:
3155:
3152:
3149:
3146:
3143:
3140:
3137:
3134:
3131:
3128:
3127:
3125:
3123:
3119:
3112:
3109:
3106:
3103:
3100:
3097:
3094:
3091:
3088:
3085:
3082:
3079:
3076:
3073:
3070:
3067:
3064:
3061:
3058:
3054:
3051:
3048:
3045:
3042:
3039:
3036:
3033:
3032:
3030:
3028:
3024:
3017:
3014:
3011:
3008:
3005:
3002:
2999:
2996:
2993:
2989:
2988:β-Eleostearic
2986:
2983:
2982:α-Eleostearic
2980:
2977:
2974:
2971:
2968:
2967:
2965:
2963:
2959:
2952:
2949:
2946:
2943:
2940:
2937:
2934:
2931:
2928:
2925:
2922:
2919:
2916:
2913:
2910:
2907:
2904:
2901:
2898:
2895:
2892:
2889:
2886:
2883:
2880:
2877:
2874:
2871:
2868:
2865:
2862:
2861:Laurolinoleic
2859:
2856:
2853:
2850:
2847:
2844:
2841:
2838:
2835:
2834:
2832:
2830:
2826:
2819:
2816:
2813:
2810:
2807:
2804:
2801:
2798:
2795:
2792:
2789:
2786:
2783:
2780:
2777:
2774:
2771:
2768:
2765:
2762:
2759:
2756:
2753:
2750:
2747:
2744:
2741:
2738:
2735:
2732:
2729:
2726:
2723:
2720:
2717:
2714:
2711:
2708:
2705:
2702:
2699:
2696:
2693:
2690:
2687:
2684:
2681:
2678:
2675:
2672:
2669:
2666:
2663:
2660:
2657:
2654:
2651:
2648:
2645:
2642:
2639:
2636:
2633:
2630:
2627:
2624:
2621:
2618:
2615:
2612:
2609:
2606:
2603:
2600:
2597:
2594:
2593:
2591:
2589:
2585:
2581:
2577:
2570:
2565:
2563:
2558:
2556:
2551:
2550:
2547:
2536:
2532:
2528:
2524:
2520:
2516:
2515:
2510:
2506:
2499:
2491:
2487:
2482:
2477:
2473:
2469:
2465:
2462:
2461:
2456:
2449:
2440:
2434:
2433:
2428:
2421:
2405:
2401:
2397:
2393:
2389:
2385:
2378:
2359:
2355:
2351:
2348:: 1334–1346.
2347:
2344:(in German).
2343:
2339:
2334:
2331:
2317:
2313:
2309:
2306:: 1324–1333.
2305:
2302:(in German).
2301:
2297:
2292:
2291:
2287:
2256:
2218:
2214:
2210:
2206:
2202:
2198:
2195:(in German).
2194:
2190:
2183:
2167:
2163:
2159:
2154:
2149:
2145:
2141:
2137:
2133:
2129:
2122:
2106:
2102:
2098:
2094:
2090:
2086:
2082:
2078:
2074:
2070:
2063:
2055:
2051:
2046:
2041:
2037:
2033:
2029:
2025:
2021:
2014:
2006:
2002:
1997:
1992:
1988:
1984:
1980:
1976:
1972:
1965:
1949:
1945:
1938:
1922:
1918:
1914:
1907:
1888:
1881:
1874:
1855:
1851:
1847:
1842:
1837:
1833:
1829:
1822:
1815:
1807:
1803:
1799:
1795:
1791:
1787:
1786:
1778:
1770:
1766:
1761:
1756:
1751:
1746:
1742:
1738:
1734:
1727:
1719:
1715:
1709:
1693:
1689:
1685:
1681:
1674:
1666:
1662:
1657:
1652:
1647:
1642:
1638:
1634:
1630:
1623:
1621:
1619:
1617:
1608:
1604:
1599:
1594:
1589:
1584:
1580:
1576:
1572:
1565:
1549:
1545:
1539:
1537:
1535:
1533:
1531:
1529:
1527:
1510:
1506:
1500:
1492:
1488:
1484:
1480:
1476:
1472:
1465:
1459:
1455:
1449:
1441:
1437:
1432:
1427:
1423:
1419:
1415:
1411:
1410:Plant Physiol
1407:
1400:
1381:
1374:
1367:
1365:
1363:
1354:
1350:
1346:
1342:
1338:
1334:
1326:
1322:
1312:
1309:
1307:
1304:
1302:
1300:
1295:
1293:
1290:
1288:
1285:
1283:
1280:
1278:
1277:Flax seed oil
1275:
1273:
1270:
1269:
1263:
1261:
1257:
1253:
1242:
1240:
1236:
1232:
1228:
1227:triglycerides
1224:
1214:
1212:
1207:
1205:
1201:
1197:
1193:
1189:
1179:
1177:
1173:
1169:
1165:
1161:
1157:
1153:
1148:
1146:
1142:
1134:
1130:
1116:average value
1110:
1107:
1104:
1102:
1099:
1096:
1094:
1091:
1090:
1087:
1084:
1082:
1079:
1076:
1074:
1071:
1070:
1067:
1064:
1062:
1061:Juglans regia
1059:
1056:
1054:
1051:
1050:
1047:
1044:
1042:
1039:
1036:
1034:
1031:
1030:
1027:
1024:
1021:
1018:
1016:
1013:
1011:
1008:
1007:
1004:
1001:
999:
996:
993:
991:
988:
987:
984:
981:
979:
976:
973:
971:
970:Sea buckthorn
968:
967:
964:
961:
959:
956:
953:
951:
948:
947:
944:
941:
939:
936:
933:
931:
930:Cuckoo flower
928:
927:
924:
921:
919:
916:
913:
911:
908:
907:
904:
901:
899:
896:
893:
891:
888:
887:
884:
881:
879:
876:
873:
871:
868:
867:
864:
861:
859:
856:
853:
851:
848:
847:
844:
841:
839:
836:
833:
831:
828:
827:
824:
821:
819:
816:
813:
810:
807:
806:
803:
800:
798:
795:
792:
790:
787:
786:
782:
780:% ALA(of oil)
779:
777:Linnaean name
776:
773:
770:
769:
766:
764:
760:
755:
751:
750:
749:Pisum sativum
745:
741:
737:
733:
729:
725:
721:
717:
711:
701:
699:
698:linoleic acid
695:
691:
687:
683:
679:
675:
671:
661:
659:
655:
651:
647:
643:
640:
636:
632:
629:
628:
623:
620:−3). It is a
619:
615:
611:
607:
602:
600:
596:
592:
588:
584:
580:
576:
574:
569:
565:
561:
558:
554:
550:
548:
543:
531:
524:
519:
502:
496:
492:
490:
487:
486:
479:
477:
474:
473:
452:
449:
445:
444:
439:
430:
425:
424:
421:
414:
400:
390:
389:
386:
379:
371:
367:
366:DTXSID7025506
363:
362:
360:
350:
346:
345:
338:
334:
333:
331:
329:
326:
325:
318:
314:
313:
311:
305:
301:
300:
293:
289:
288:
286:
283:
279:
278:
274:
270:
267:
265:
263:ECHA InfoCard
260:
259:
252:
248:
247:
245:
243:
240:
239:
232:
228:
227:
225:
223:
220:
219:
212:
208:
207:
205:
203:
200:
199:
192:
188:
187:
185:
183:
180:
179:
172:
168:
165:
161:
160:
158:
154:
149:
148:
141:
137:
136:
134:
131:
127:
126:
121:
116:
112:
108:
104:
100:
96:
89:
83:
79:
75:
69:
65:
60:
56:
51:
47:
42:
36:
32:
27:
19:
3282:8-Eicosenoic
3276:Petroselinic
3182:
3056:
3053:Linolelaidic
2991:
2933:Clupanodonic
2896:
2891:Palmitidonic
2728:Pentacosylic
2704:Heneicosylic
2668:Pentadecylic
2518:
2512:
2508:
2504:
2498:
2463:
2458:
2448:
2438:
2430:
2420:
2408:. Retrieved
2391:
2387:
2377:
2362:. Retrieved
2345:
2341:
2329:
2320:. Retrieved
2303:
2299:
2286:
2230:
2221:. Retrieved
2196:
2192:
2182:
2170:. Retrieved
2135:
2131:
2121:
2109:. Retrieved
2076:
2072:
2062:
2027:
2023:
2013:
1978:
1974:
1964:
1952:. Retrieved
1948:the original
1937:
1925:. Retrieved
1921:the original
1916:
1906:
1894:. Retrieved
1887:the original
1873:
1861:. Retrieved
1831:
1827:
1814:
1789:
1783:
1777:
1740:
1736:
1726:
1718:the original
1708:
1696:. Retrieved
1683:
1673:
1636:
1632:
1578:
1574:
1564:
1552:. Retrieved
1513:. Retrieved
1499:
1474:
1470:
1464:
1453:
1448:
1413:
1409:
1399:
1387:. Retrieved
1339:(1): 65–78.
1336:
1332:
1325:
1298:
1248:
1220:
1208:
1185:
1175:
1149:
1145:stearic acid
1138:
1100:
1080:
1060:
1040:
1019:
998:Rubus idaeus
997:
977:
957:
937:
917:
897:
877:
857:
837:
817:
796:
754:chloroplasts
747:
713:
689:
681:
673:
669:
667:
653:
641:
634:
631:double bonds
625:
617:
613:
609:
603:
572:
563:
559:
552:
546:
545:
541:
540:
493:0.9164 g/cm
123:Identifiers
114:
110:
106:
102:
98:
94:
91:Other names
81:
77:
73:
35:
26:
3309:Fatty acids
3130:Palmitoleic
3099:Arachidonic
3063:γ-Linolenic
2970:Myristoleic
2909:α-Parinaric
2903:Stearidonic
2897:α-Linolenic
2849:Decadienoic
2788:Ceroplastic
2752:Nonacosylic
2692:Nonadecylic
2580:fatty acids
2460:Biochem. J.
2199:: 260–270.
2172:14 December
2111:14 December
1515:30 December
1389:22 February
1200:soybean oil
1196:hydrogenate
1101:Glycine max
870:Lingonberry
771:Common name
728:linseed oil
646:regioisomer
441:Properties
269:100.006.669
191:CHEBI:27432
3298:Categories
2740:Carboceric
2722:Lignoceric
2716:Tricosylic
2656:Tridecylic
2632:Pelargonic
2364:31 October
2322:31 October
2223:1 November
1942:Monsanto.
1896:11 January
1863:4 November
1743:(33): 33.
1698:28 October
1688:ASHS Press
1317:References
1287:Drying oil
1272:Canola oil
1211:trans fats
1141:desaturase
1124:Metabolism
759:polymerize
708:See also:
694:oleic acid
476:Molar mass
337:0RBV727H71
282:IUPHAR/BPS
222:ChemSpider
211:ChEMBL8739
151:3D model (
130:CAS Number
3148:Paullinic
3093:Sciadonic
3075:Pinolenic
2855:Lauroleic
2770:Lacceroic
2698:Arachidic
2644:Undecylic
2596:Propionic
2588:Saturated
2535:196696819
2514:Synthesis
2213:197767239
2138:: n2213.
2101:220439436
1954:6 January
1927:3 January
1633:Molecules
1010:Blueberry
994:raspberry
990:Raspberry
950:Cranberry
934:mayflower
914:portulaca
809:Kiwifruit
793:chia sage
670:linolenic
668:The word
664:Etymology
606:structure
570:), is an
3251:Gadoleic
3232:Sapienic
3201:Nervonic
3136:Vaccenic
3069:Calendic
3047:Linoleic
2843:Decenoic
2837:Octenoic
2758:Melissic
2746:Montanic
2680:Margaric
2674:Palmitic
2662:Myristic
2626:Caprylic
2620:Enanthic
2490:16745822
2404:Archived
2358:Archived
2316:Archived
2217:Archived
2166:Archived
2162:34645650
2105:Archived
2093:32643951
2054:23076616
2005:35170723
1854:Archived
1850:16188209
1806:17920214
1769:19664246
1692:Archived
1665:34946523
1607:35158619
1554:26 March
1548:Archived
1509:Archived
1491:11879055
1440:16662966
1380:Archived
1353:10878236
1297:List of
1266:See also
1204:Soybeans
1073:Rapeseed
1037:cannabis
1015:bilberry
974:seaberry
910:Purslane
894:camelina
890:Camelina
874:cowberry
740:soybeans
732:rapeseed
724:flaxseed
674:linoleic
583:flaxseed
566:meaning
555:) (from
242:DrugBank
140:463-40-1
3189:Gondoic
3179:Elaidic
3142:Rumenic
3105:Adrenic
2998:Punicic
2776:Psyllic
2734:Cerotic
2710:Behenic
2686:Stearic
2614:Caproic
2608:Valeric
2602:Butyric
2481:1266662
2153:8513503
2132:The BMJ
2045:3497923
1996:9526859
1760:3224740
1656:8704999
1598:8833380
1575:Animals
1431:1066200
1245:History
1112:
1093:Soybean
854:linseed
830:Perilla
738:), and
720:perilla
587:walnuts
523:what is
521: (
489:Density
481:278.436
317:5280934
304:PubChem
251:DB00132
231:4444437
3284:(20:1)
3278:(18:1)
3272:(16:1)
3253:(20:1)
3234:(16:1)
3215:(20:3)
3209:(20:2)
3203:(24:1)
3197:(22:1)
3195:Erucic
3191:(20:1)
3185:-18:1)
3175:(18:1)
3156:(20:3)
3150:(20:1)
3144:(18:2)
3138:(18:1)
3132:(16:1)
3113:(22:5)
3111:Osbond
3107:(22:4)
3101:(20:4)
3095:(20:3)
3089:(20:3)
3083:(20:2)
3077:(18:3)
3071:(18:3)
3065:(18:3)
3059:-18:2)
3049:(18:2)
3043:(18:1)
3037:(14:1)
3018:(20:4)
3012:(20:3)
3006:(18:3)
3000:(18:3)
2994:-18:3)
2984:(18:3)
2978:(16:1)
2972:(14:1)
2953:(24:6)
2947:(24:5)
2941:(22:6)
2935:(22:5)
2929:(20:5)
2923:(20:4)
2917:(20:3)
2911:(18:4)
2905:(18:4)
2899:(18:3)
2893:(16:4)
2887:(16:3)
2881:(14:3)
2875:(14:2)
2869:(14:1)
2863:(12:2)
2857:(12:1)
2851:(10:2)
2845:(10:1)
2782:Geddic
2650:Lauric
2638:Capric
2576:Lipids
2533:
2488:
2478:
2410:1 July
2211:
2160:
2150:
2099:
2091:
2052:
2042:
2003:
1993:
1848:
1804:
1767:
1757:
1663:
1653:
1605:
1595:
1489:
1438:
1428:
1351:
1237:, and
1217:Health
1077:canola
1053:Walnut
736:canola
518:verify
515:
420:SMILES
202:ChEMBL
62:Names
3183:trans
3173:Oleic
3057:trans
2992:trans
2839:(8:1)
2820:(C40)
2814:(C39)
2808:(C38)
2802:(C37)
2796:(C36)
2790:(C35)
2784:(C34)
2778:(C33)
2772:(C32)
2766:(C31)
2760:(C30)
2754:(C29)
2748:(C28)
2742:(C27)
2736:(C26)
2730:(C25)
2724:(C24)
2718:(C23)
2712:(C22)
2706:(C21)
2700:(C20)
2694:(C19)
2688:(C18)
2682:(C17)
2676:(C16)
2670:(C15)
2664:(C14)
2658:(C13)
2652:(C12)
2646:(C11)
2640:(C10)
2531:S2CID
2290:See:
2209:S2CID
2097:S2CID
1890:(PDF)
1883:(PDF)
1857:(PDF)
1824:(PDF)
1383:(PDF)
1376:(PDF)
1065:10.4%
834:shiso
811:seeds
783:ref.
763:paint
690:Oleic
682:linon
680:word
678:Greek
564:linon
560:alpha
557:Greek
547:alpha
385:InChI
182:ChEBI
153:JSmol
3213:Mead
2634:(C9)
2628:(C8)
2622:(C7)
2616:(C6)
2610:(C5)
2604:(C4)
2598:(C3)
2519:1995
2486:PMID
2412:2019
2366:2020
2324:2020
2225:2020
2174:2021
2158:PMID
2113:2021
2089:PMID
2050:PMID
2001:PMID
1956:2007
1929:2007
1898:2007
1865:2018
1846:PMID
1802:PMID
1765:PMID
1700:2006
1661:PMID
1603:PMID
1556:2018
1517:2012
1487:PMID
1436:PMID
1391:2006
1349:PMID
1133:Flax
1097:soya
1033:Hemp
850:Flax
789:Chia
716:chia
686:flax
595:hemp
591:chia
568:flax
328:UNII
292:1049
2523:doi
2476:PMC
2468:doi
2396:doi
2350:doi
2308:doi
2201:doi
2148:PMC
2140:doi
2136:375
2081:doi
2040:PMC
2032:doi
1991:PMC
1983:doi
1836:doi
1794:doi
1755:PMC
1745:doi
1651:PMC
1641:doi
1593:PMC
1583:doi
1479:doi
1426:PMC
1418:doi
1341:doi
1337:106
1085:10%
1045:20%
1025:29%
1002:31%
982:32%
962:35%
942:35%
922:35%
902:37%
882:49%
862:55%
842:58%
822:62%
801:64%
730:),
688:).
648:of
627:cis
614:cis
610:all
553:ALA
354:EPA
307:CID
113:,15
109:,12
103:cis
99:cis
95:cis
80:,15
76:,12
3300::
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2529:.
2517:.
2484:.
2474:.
2464:29
2457:.
2436:;
2429:.
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2392:62
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2271:18
2263:32
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2245:18
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1979:13
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1800:.
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1105:8%
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