429:
800:(AI) for omega−3 fatty acids is for ALA. It is based on the median intake, and for adults the values are 1.6 g/day for men and 1.1 g/day for women. EPA and DHA contribute about 10 percent of total omega−3 intake. The AI for omega−6 fatty acids is for linoleic acid and is also based on the median intake: 17 g/day for younger men, dropping to 14 g/day for men over 50 years old; for younger women 12 g/d, and 11 g/day for women over 50. Studies have shown that smaller intakes reverse the symptoms of deficiency, but there is inadequate information to set an
582:
lower blood levels of DHA than through direct ingestion. This is illustrated by studies in vegans and vegetarians. If there is relatively more LA than ALA in the diet it favors the formation of DPA from LA rather than DHA from ALA. This effect can be altered by changing the relative ratio of LA:ALA, but is more effective when total intake of polyunsaturated fatty acids is low.
601:
skin symptoms. This could be treated by infusing lipids, and later studies showed that topical application of sunflower oil would also resolve the dermal symptoms. Linoleic acid has a specific role in maintaining the skin water-permeability barrier, probably as constituents of acylglycosylceramides. This role cannot be met by any ω−3 fatty acids or by arachidonic acid.
405:, the minus symbol represents subtraction, indicating how many carbons away from the terminal end (ω) of the chain that the first unsaturated carbon-carbon bond appears. Typically, the number of carbons and the number of double bonds are also listed in short descriptions of unsaturated fatty acids. For instance, ω−3 18:4, or 18:4 ω−3, or 18:4 n−3 indicate
585:
In preterm infants, the capacity to convert LA to AA and ALA to DHA is limited, and preformed AA and DHA may be required to meet the needs of the developing brain. Both AA and DHA are present in breastmilk and contribute along with the parent fatty acids LA and ALA to meeting the requirements of the
719:
lists notable vegetable sources of EFAs as well as commentary and an overview of the biosynthetic pathways involved. However, these sources are not in perfect agreement. EFA content of vegetable sources varies with cultivation conditions. Animal sources vary widely, both with the animal's feed and
596:
in sufficient quantities for normal physiological function. This definition is met for LA and ALA but not the longer chain derivatives in adults. The longer chain derivatives particularly, however, have pharmacological properties that can modulate disease processes, but this should not be confused
581:
In humans, arachidonic acid (20:4n−6; AA) can be synthesized from LA. In turn, AA can be converted to an even longer fatty acid, the docosapentaenoic acid (22:5n−6; DPA). Similarly, ALA can be converted to docosahexaenoic acid (22:6n−3; DHA), although the latter conversion is limited, resulting in
694:
Fish is the main source of the longer omega−3 fats; eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), though they initially acquire these fats through the consumption of algae and seaweed. Some plant-based foods contain omega−3 in the form of alpha-linolenic acid (ALA), which appears to
600:
One study demonstrated linoleic acid deficiency in adults. They found that patients undergoing intravenous nutrition with glucose became isolated from their fat supplies and rapidly developed biochemical signs of essential fatty acid deficiency (an increase in 20:3n−9/20:4n−6 ratio in plasma) and
699:
or supplements derived from them are consumed) convert ALA to EPA and subsequently DHA. This elongation of ALA is inefficient. Conversion to DHA is higher in women than in men; this is thought to reflect the need to provide DHA to the fetus and infant during pregnancy and breast feeding.
734:
Essential fatty acids play an important role in the life and death of cardiac cells. Additionally, essential fatty acids are crucial for the development of several endocannabinoids with a multitude of functions in the body, such as docosahexaenoyl ethanolamide (DHA-EA/synaptamide).
619:
Reviews by the
European Food Safety Authority made recommendations for minimal intakes of LA and ALA and have also recommended intakes of longer chain ω−3 fatty acids based on the association of oily fish consumption with a lower risk of cardiovascular disease.
393:) at the other end. They are almost always straight-chained. The carbon next to the carboxylate is known as α, the next carbon β, and so forth. Since biological fatty acids can be of diverse lengths, the last position is often labelled as "
254:, but the conversion amount is small, requiring intake from food or supplements. Deficiency in omega−3 fatty acids are very common. The average American has a dietry ratio between omega−6 fatty acids and omega−3 fatty acids of 20:1.
578:(18:3n−3; ALA) are essential for humans in the diet. However, humans can convert both LA and ALA to fatty acids with longer carbon chains and a larger number of double bonds, by alternative desaturation and chain elongation.
428:
687:, and there is evidence to suggest that low levels of essential fatty acids, or the wrong balance of types among the essential fatty acids, may be a factor in a number of illnesses, including
1587:"EFSA Scientific Opinion on Dietary Reference Values for fats, including saturated fatty acids, polyunsaturated fatty acids, monounsaturated fatty acids, trans fatty acids and cholesterol"
2130:
257:
When the two EFAs were discovered in 1923, they were designated "vitamin F", but in 1929, research on rats showed that the two EFAs are better classified as
997:
574:
Mammals lack the ability to introduce double bonds in fatty acids beyond carbon 9 and 10, hence the omega−6 linoleic acid (18:2n−6; LA) and the omega−3
1618:
Nugent KP, Spigelman AD, Phillips RK (June 1996). "Tissue prostaglandin levels in familial adenomatous polyposis patients treated with sulindac".
280:
In the body, essential fatty acids serve multiple functions. In each of these, the balance between dietary ω−3 and ω−6 strongly affects function.
1919:
1431:
FAO/WHO Fats and fatty acids in human nutrition. Report of an expert consultation. FAO Food and
Nutrition Paper 91, Rome 2011. ISSN 0254-4725
560:
Except for GLA, which has a short 18-carbon chain, these fatty acids have more than 18 carbon atoms and are typically classified as LC-PUFA.
1844:
1872:
246:). These are supplied to the body either as the free fatty acid, or more commonly as some glyceride derivative. ALA can be converted into
1478:"Correction of the cutaneous manifestations of essential fatty acid deficiency in man by application of sunflower-seed oil to the skin"
695:
have a modest benefit for cardiovascular health. The human body can (and in case of a purely vegetarian diet often must unless certain
2198:
1441:
Collins FD, Sinclair AJ, Royle JP, Coats DA, Maynard AT, Leonard RF (1971). "Plasma lipids in human linoleic acid deficiency".
509:
They form the starting point for the creation of more desaturated fatty acids, most of which also have a longer carbon chain:
1007:
980:
1900:
586:
newborn infant. Many infant formulas have AA and DHA added to them with an aim to make them more equivalent to human milk.
604:
The main physiological requirement for ω−6 fatty acids is attributed to arachidonic acid, which is the major precursor of
707:
provides a very large and detailed listing of fat contents of animal and vegetable fats, including ω−3 and −6 oils. The
864:
409:, an 18-carbon chain with 4 double bonds, and with a double bond between the third and fourth carbon atoms from the CH
2165:
1714:
he turnover of essential fatty acids is increased (7). Arachidonic acid is one of the essential fatty acids affected.
1569:
874:
274:
2131:"DIETARY REFERENCE INTAKES for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids"
2306:
2137:
1726:
Kruger MC, Horrobin DF (September 1997). "Calcium metabolism, osteoporosis and essential fatty acids: a review".
2665:
2593:
744:
273:
For the biological effects of the ω−3 and ω−6 fatty acids which are mediated by their mutual interactions, see
215:
and for the maintenance and function of tissues and organs. These fatty acids also are precursors to vitamins,
167:
708:
1938:"External blockade of the major cardiac delayed-rectifier K+ channel (Kv1.5) by polyunsaturated fatty acids"
2191:
842:
743:
Reference intake values for as published by the Panel on
Dietetic Products, Nutrition and Allergies of the
941:
545:
423:) group unless otherwise noted. In free fatty acid form, the chemical structure of stearidonic acid is:
2349:
2344:
440:
566:
are not essential in humans because they can be synthesized from carbohydrates or other fatty acids.
2154:
James, William D.; Elston, Dirk; Treat, James R.; Rosenbach, Misha A.; Neuhaus, Isaac (2019-01-18).
1916:
1257:"n-3 fatty acids, inflammation, and immunity--relevance to postsurgical and critically ill patients"
2583:
1666:"Pathological regulation of arachidonic acid release in cystic fibrosis: the putative basic defect"
801:
797:
333:
309:
which are a group of eicosanoid derivatives formed via the lipoxygenase pathway from ω−6 EFAs and
2184:
216:
141:
1812:"Conversion of alpha-linolenic acid to longer-chain polyunsaturated fatty acids in human adults"
1811:
1861:
729:
2155:
972:
965:
894:
879:
519:
247:
1763:"α-Linolenic acid and risk of cardiovascular disease: a systematic review and meta-analysis"
616:. Metabolites from the ω−3 pathway, mainly from eicosapentaenoic acid, are mostly inactive.
2578:
2299:
1949:
1677:
869:
764:
575:
539:
525:
472:
251:
200:
299:
8:
1215:
1123:
Das, Undurti N. (2006). "Essential Fatty Acids: Biochemistry, Physiology and
Pathology".
914:
884:
414:
58:
53:
1953:
1681:
2573:
2399:
2394:
2389:
2258:
2248:
2031:
1995:
Reiffel JA, McDonald A (August 2006). "Antiarrhythmic effects of omega-3 fatty acids".
1787:
1762:
1643:
1519:"The endocannabinoid system, anandamide and the regulation of mammalian cell apoptosis"
1333:
1308:
1281:
1256:
1148:
1056:
1031:
909:
904:
563:
533:
513:
480:
466:
243:
239:
208:
160:
101:
96:
91:
86:
1739:
1700:
1665:
1199:
1182:
2161:
2111:
2070:
2043:
2012:
1977:
1972:
1937:
1836:
1792:
1743:
1705:
1635:
1565:
1540:
1499:
1458:
1414:
1379:
1338:
1286:
1237:
1140:
1102:
1061:
1003:
976:
824:
715:. This lists 40 common oils, more tightly focused on EFAs and sorted by n−6:3 ratio.
212:
129:
1647:
1152:
369:
238:
Only two fatty acids are known to be essential for humans: alpha-linolenic acid (an
2417:
2101:
2004:
1967:
1957:
1826:
1782:
1774:
1735:
1695:
1685:
1627:
1598:
1530:
1489:
1450:
1406:
1369:
1328:
1320:
1276:
1268:
1227:
1194:
1132:
1092:
1051:
1043:
944:. Office of Dietary Supplements, US National Institutes of Health. 15 February 2023
661:
551:
406:
2008:
1309:"Selection in Europeans on Fatty Acid Desaturases Associated with Dietary Changes"
2495:
2339:
2292:
1923:
1559:
1494:
1477:
820:
673:
669:
48:
1889:
1410:
2634:
2485:
2207:
2090:"Labelling reference intake values for n-3 and n-6 polyunsaturated fatty acids"
1942:
Proceedings of the
National Academy of Sciences of the United States of America
1670:
Proceedings of the
National Academy of Sciences of the United States of America
605:
398:
382:
337:
313:
from ω−3 (in the presence of acetylsalicylic acid, downregulating inflammation)
1272:
1047:
2659:
2513:
2475:
2470:
2455:
2422:
2334:
2228:
2218:
2115:
2106:
2089:
1603:
1586:
1374:
1357:
1097:
1080:
852:
781:
486:
220:
204:
153:
43:
20:
1778:
1690:
1324:
2603:
2565:
2528:
2523:
2490:
2480:
2427:
2223:
2074:
2047:
2016:
1962:
1840:
1796:
1544:
1535:
1518:
1418:
1383:
1342:
1290:
1241:
1144:
1136:
1065:
688:
665:
641:
609:
496:
386:
292:
196:
108:
1981:
1831:
1747:
1709:
1639:
1503:
1462:
1232:
1106:
2644:
2639:
2629:
2588:
2538:
2533:
2518:
2465:
2460:
2437:
2432:
2032:"[Alpha-linolenic acid, cardiovascular disease and sudden death]"
857:
847:
720:
that the EFA makeup varies markedly with fats from different body parts.
653:
378:
325:
228:
224:
199:. As they are not synthesized in the body, the essential fatty acids –
113:
612:
that play a vital role in cell signaling, and an endogenous cannabinoid
351:
They act on DNA (activating or inhibiting transcription factors such as
2447:
2409:
1631:
837:
816:
684:
657:
613:
500:
345:
321:
288:
192:
188:
76:
1454:
2505:
2384:
2243:
2087:
1216:"Docosahexaenoic acid affects cell signaling by altering lipid rafts"
899:
889:
649:
645:
633:
375:
329:
310:
134:
1936:
Honoré E, Barhanin J, Attali B, Lesage F, Lazdunski M (March 1994).
462:
Both the essential fatty acids are SC-PUFA with an 18-carbon chain:
2611:
2553:
2548:
1032:"Essential fatty acids as functional components of foods- a review"
356:
317:
2284:
1214:
Stillwell W, Shaikh SR, Zerouga M, Siddiqui R, Wassall SR (2005).
1183:"On the nature and role of the fatty acids essential in nutrition"
962:
352:
2621:
2543:
2268:
2263:
2176:
1663:
1081:"Deficiencies of essential and conditionally essential nutrients"
503:
306:
262:
232:
2233:
677:
1213:
2316:
2273:
2253:
1664:
Carlstedt-Duke J, Brönnegård M, Strandvik B (December 1986).
996:
Vaughan JG, Geissler C, Nicholson B, Dowle E, Rice E (2009).
995:
696:
394:
1170:(11th ed.). California: Thomson Wadsworth. p. 154.
637:
629:
34:
1935:
443:
with 16- and 18-carbon chains are sometimes classified as
2368:
2363:
2153:
1761:
Pan A, Chen M, Chowdhury R, et al. (December 2012).
1440:
1078:
971:(6th ed.). Philadelphia: Lea and Febinger. pp.
258:
191:
that are required by humans and other animals for normal
30:
2128:
628:
Some of the food sources of ω−3 and ω−6 fatty acids are
211:. Essential fatty acids are needed for various cellular
1617:
1079:
Chipponi JX, Bleier JC, Santi MT, Rudman D (May 1982).
1516:
1165:
1358:"Essential fatty acids in health and chronic disease"
2088:
European Food Safety
Authority (EFSA) (2009-07-01).
2157:
1475:
989:
964:
807:
1917:Vegetable Lipids as Components of Functional Food
1517:Maccarrone, M; Finazzi-Agró, A (22 August 2003).
1399:Prostaglandins Leukotrienes Essential Fatty Acids
717:Vegetable Lipids as Components of Functional Food
2657:
1760:
1397:Sanders TA (2009). "DHA Status of vegetarians".
1002:. Oxford University Press US. pp. 212–235.
592:are defined as those that cannot be synthesized
1994:
363:
1725:
1029:
2300:
2192:
963:Robert S. Goodhart; Maurice E. Shils (1980).
569:
161:
16:Fatty acids required for biological processes
1809:
1652:Arachidonic acid is an essential fatty acid…
1557:
2029:
302:(affecting mood, behavior and inflammation)
2307:
2293:
2199:
2185:
1362:The American Journal of Clinical Nutrition
1355:
1085:The American Journal of Clinical Nutrition
1030:Kaur N, Chugh V, Gupta AK (October 2014).
738:
683:Essential fatty acids play a part in many
168:
154:
2160:. Elsevier Health Sciences. p. 482.
2105:
2060:
1971:
1961:
1830:
1786:
1699:
1689:
1657:
1602:
1534:
1493:
1476:Prottey, C; Hartop, PJ; Press, M (1975).
1373:
1332:
1280:
1254:
1231:
1207:
1198:
1096:
1055:
459:), which have more than 18 carbon atoms.
1180:
385:(–COOH) at one end, and terminated by a
2147:
1810:Burdge GC, Calder PC (September 2005).
1396:
1306:
1302:
1300:
1248:
445:short chain polyunsaturated fatty acids
419:and separated by a single methylene (CH
207:– must be obtained from food or from a
2658:
2036:Tidsskrift for den Norske Lægeforening
1611:
1036:Journal of Food Science and Technology
967:Modern Nutrition in Health and Disease
453:long-chain polyunsaturated fatty acids
355:, which is linked to pro-inflammatory
2288:
2180:
1584:
1118:
1116:
936:
934:
932:
930:
2030:Landmark K, Alm CS (November 2006).
1297:
1220:Reproduction, Nutrition, Development
2314:
1558:Sanders, Tom; Emery, Peter (2003).
1174:
1122:
1072:
1023:
13:
2206:
2136:. pp. 422–514. Archived from
1997:The American Journal of Cardiology
1561:Molecular Basis of Human Nutrition
1113:
999:The new Oxford book of food plants
927:
865:Specialized proresolving mediators
499:by humans because humans lack the
295:and many other cellular functions)
14:
2677:
2129:Food and Nutrition Board (2004).
1166:Whitney Ellie; Rolfes SR (2008).
875:Essential fatty acid interactions
711:'s EFA Education group publishes
275:Essential fatty acid interactions
2061:Herbaut C (September 2006). "".
1906:from the original on 2014-12-10.
1878:from the original on 2006-02-12.
1850:from the original on 2017-08-15.
1620:Diseases of the Colon and Rectum
1523:Cell Death & Differentiation
1307:Buckley MT, et al. (2017).
495:These two fatty acids cannot be
427:
2122:
2081:
2054:
2023:
1988:
1929:
1910:
1882:
1854:
1803:
1754:
1719:
1578:
1551:
1510:
1469:
1434:
1425:
1390:
1356:Simopoulos, Artemis P. (1999).
1349:
1181:Burr GO, Burr MM (April 1930).
813:Essential fatty acid deficiency
808:Essential fatty acid deficiency
723:
623:
506:required for their production.
2594:Dipalmitoylphosphatidylcholine
2259:"Minerals" (Chemical elements)
1159:
956:
745:European Food Safety Authority
370:Fatty acid § Nomenclature
348:(affecting cellular signaling)
1:
2009:10.1016/j.amjcard.2005.12.027
1890:"Essential Fats in Food Oils"
1740:10.1016/S0163-7827(97)00007-6
1200:10.1016/S0021-9258(20)78929-5
921:
802:Estimated Average Requirement
709:National Institutes of Health
219:, and derivatives, including
1495:10.1111/1523-1747.ep12510667
843:Hydroxyeicosatetraenoic acid
364:Nomenclature and terminology
268:
7:
2063:Revue Médicale de Bruxelles
1411:10.1016/j.plefa.2009.05.013
1255:Calder PC (December 2004).
830:
713:Essential Fats in Food Oils
597:with dietary essentiality.
546:dihomo-gamma-linolenic acid
441:Polyunsaturated fatty acids
435:
10:
2682:
2350:Polyunsaturated fatty acid
2345:Monounsaturated fatty acid
1728:Progress in Lipid Research
1564:. London: Taylor Frances.
796:In the United States, the
727:
570:Essentiality in human diet
397:", the last letter in the
367:
284:They are modified to make
272:
18:
2620:
2602:
2584:Phosphatidyl ethanolamine
2564:
2504:
2446:
2408:
2377:
2323:
2214:
1273:10.1007/s11745-004-1342-z
1048:10.1007/s13197-012-0677-0
334:epoxyeicosatrienoic acids
2107:10.2903/j.efsa.2009.1176
1604:10.2903/j.efsa.2010.1461
819:similar to that seen in
759:Reference intake values
374:Fatty acids comprise an
242:) and linoleic acid (an
19:Not to be confused with
1779:10.3945/ajcn.112.044040
1691:10.1073/pnas.83.23.9202
1168:Understanding Nutrition
739:Reference intake values
197:synthesized in the body
142:Fat interesterification
1963:10.1073/pnas.91.5.1937
1862:"IUPAC Lipid Handbook"
1536:10.1038/sj.cdd.4401284
1375:10.1093/ajcn/70.3.560s
1137:10.1002/biot.200600012
1098:10.1093/ajcn/35.5.1112
730:Diet and heart disease
413:end. Double bonds are
193:physiological function
2666:Essential fatty acids
2239:Essential fatty acids
1769:(Systematic review).
1325:10.1093/molbev/msx103
1125:Biotechnology Journal
942:"Omega-3 Fatty Acids"
895:Nonclassic eicosanoid
880:Fatty acid metabolism
658:canola (rapeseed) oil
520:eicosapentaenoic acid
248:eicosapentaenoic acid
181:Essential fatty acids
2579:Phosphatidylinositol
2355:Essential fatty acid
870:Essential amino acid
705:IUPAC Lipid Handbook
576:alpha-linolenic acid
540:gamma-linolenic acid
526:docosahexaenoic acid
401:. In the expression
252:docosahexaenoic acid
201:alpha-linolenic acid
81:Essential fatty acid
1954:1994PNAS...91.1937H
1832:10.1051/rnd:2005047
1682:1986PNAS...83.9202C
1233:10.1051/rnd:2005046
1091:(5 Suppl): 1112–6.
915:Polyunsaturated fat
885:Fatty acid synthase
685:metabolic processes
590:Essential nutrients
213:metabolic processes
59:Polyunsaturated fat
54:Monounsaturated fat
2574:Phosphatidylserine
2400:Omega−9 fatty acid
2395:Omega−6 fatty acid
2390:Omega−3 fatty acid
1926:, Stuchlik and Zak
1922:2006-03-20 at the
1767:Am. J. Clin. Nutr.
1632:10.1007/BF02056946
910:Omega−6 fatty acid
905:Omega−3 fatty acid
804:(EAR) for either.
244:omega−6 fatty acid
240:omega−3 fatty acid
209:dietary supplement
2653:
2652:
2282:
2281:
1819:Reprod. Nutr. Dev
1585:Jones, A (2010).
1482:J Invest Dermatol
1455:10.1159/000175332
1009:978-0-19-954946-7
982:978-0-8121-0645-9
825:biotin deficiency
794:
793:
548:or DGLA (20:3n−6)
451:), as opposed to
178:
177:
130:Fat hydrogenation
122:Manufactured fats
2673:
2418:Arachidonic acid
2309:
2302:
2295:
2286:
2285:
2201:
2194:
2187:
2178:
2177:
2172:
2171:
2151:
2145:
2144:
2142:
2135:
2126:
2120:
2119:
2109:
2085:
2079:
2078:
2058:
2052:
2051:
2038:(in Norwegian).
2027:
2021:
2020:
1992:
1986:
1985:
1975:
1965:
1933:
1927:
1914:
1908:
1907:
1905:
1897:efaeducation.org
1894:
1886:
1880:
1879:
1877:
1866:
1858:
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1834:
1816:
1807:
1801:
1800:
1790:
1758:
1752:
1751:
1723:
1717:
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1703:
1693:
1661:
1655:
1654:
1615:
1609:
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1576:
1575:
1555:
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1548:
1538:
1514:
1508:
1507:
1497:
1473:
1467:
1466:
1438:
1432:
1429:
1423:
1422:
1394:
1388:
1387:
1377:
1368:(3): 560s–569s.
1353:
1347:
1346:
1336:
1319:(6): 1307–1318.
1304:
1295:
1294:
1284:
1252:
1246:
1245:
1235:
1211:
1205:
1204:
1202:
1178:
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1163:
1157:
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1120:
1111:
1110:
1100:
1076:
1070:
1069:
1059:
1042:(10): 2289–303.
1027:
1021:
1020:
1018:
1016:
993:
987:
986:
970:
960:
954:
953:
951:
949:
938:
750:
749:
674:leafy vegetables
552:arachidonic acid
542:or GLA (18:3n−6)
528:or DHA (22:6n−3)
522:or EPA (20:5n−3)
475:or ALA (18:3n−3)
473:α-linolenic acid
431:
407:stearidonic acid
338:neuroprotectin D
300:endocannabinoids
170:
163:
156:
26:
25:
2681:
2680:
2676:
2675:
2674:
2672:
2671:
2670:
2656:
2655:
2654:
2649:
2635:Corticosteroids
2616:
2598:
2560:
2500:
2496:Lignoceric acid
2442:
2404:
2373:
2340:Unsaturated fat
2319:
2313:
2283:
2278:
2210:
2205:
2175:
2168:
2152:
2148:
2140:
2133:
2127:
2123:
2086:
2082:
2059:
2055:
2028:
2024:
2003:(4A): 50i–60i.
1993:
1989:
1934:
1930:
1924:Wayback Machine
1915:
1911:
1903:
1892:
1888:
1887:
1883:
1875:
1864:
1860:
1859:
1855:
1847:
1814:
1808:
1804:
1759:
1755:
1734:(2–3): 131–51.
1724:
1720:
1662:
1658:
1616:
1612:
1583:
1579:
1572:
1556:
1552:
1515:
1511:
1474:
1470:
1439:
1435:
1430:
1426:
1405:(2–3): 137–41.
1395:
1391:
1354:
1350:
1305:
1298:
1267:(12): 1147–61.
1253:
1249:
1212:
1208:
1179:
1175:
1164:
1160:
1121:
1114:
1077:
1073:
1028:
1024:
1014:
1012:
1010:
994:
990:
983:
961:
957:
947:
945:
940:
939:
928:
924:
919:
833:
810:
798:Adequate Intake
768:-Linolenic acid
741:
732:
726:
670:sunflower seeds
636:, seaweed oil,
626:
572:
564:ω−9 fatty acids
554:or AA (20:4n−6)
534:ω−6 fatty acids
514:ω−3 fatty acids
489:or LA (18:2n−6)
438:
422:
412:
392:
372:
366:
278:
271:
195:that cannot be
174:
49:Unsaturated fat
24:
17:
12:
11:
5:
2679:
2669:
2668:
2651:
2650:
2648:
2647:
2642:
2637:
2632:
2626:
2624:
2618:
2617:
2615:
2614:
2608:
2606:
2600:
2599:
2597:
2596:
2591:
2586:
2581:
2576:
2570:
2568:
2562:
2561:
2559:
2558:
2557:
2556:
2551:
2546:
2541:
2536:
2531:
2521:
2516:
2510:
2508:
2502:
2501:
2499:
2498:
2493:
2488:
2486:Arachidic acid
2483:
2478:
2473:
2468:
2463:
2458:
2452:
2450:
2444:
2443:
2441:
2440:
2435:
2430:
2425:
2423:Prostaglandins
2420:
2414:
2412:
2406:
2405:
2403:
2402:
2397:
2392:
2387:
2381:
2379:
2375:
2374:
2372:
2371:
2366:
2357:
2352:
2347:
2342:
2337:
2327:
2325:
2321:
2320:
2312:
2311:
2304:
2297:
2289:
2280:
2279:
2277:
2276:
2271:
2266:
2261:
2256:
2251:
2246:
2241:
2236:
2231:
2226:
2221:
2215:
2212:
2211:
2208:Food chemistry
2204:
2203:
2196:
2189:
2181:
2174:
2173:
2166:
2146:
2143:on 2022-06-27.
2121:
2080:
2069:(4): S355–60.
2053:
2042:(21): 2792–4.
2022:
1987:
1948:(5): 1937–41.
1928:
1909:
1881:
1853:
1802:
1773:(6): 1262–73.
1753:
1718:
1676:(23): 9202–6.
1656:
1610:
1577:
1570:
1550:
1529:(9): 946–955.
1509:
1468:
1433:
1424:
1389:
1348:
1296:
1247:
1206:
1193:(2): 587–621.
1173:
1158:
1131:(4): 420–439.
1112:
1071:
1022:
1008:
988:
981:
955:
925:
923:
920:
918:
917:
912:
907:
902:
897:
892:
887:
882:
877:
872:
867:
862:
861:
860:
855:
850:
845:
834:
832:
829:
809:
806:
792:
791:
788:
785:
778:
777:
774:
771:
761:
760:
757:
754:
740:
737:
728:Main article:
725:
722:
640:(linseed) and
625:
622:
606:prostaglandins
571:
568:
558:
557:
556:
555:
549:
543:
531:
530:
529:
523:
493:
492:
491:
490:
481:ω−6 fatty acid
478:
477:
476:
467:ω−3 fatty acid
437:
434:
433:
432:
420:
410:
399:Greek alphabet
390:
383:carboxyl group
368:Main article:
365:
362:
361:
360:
349:
342:
341:
340:
314:
303:
296:
270:
267:
235:, and others.
221:prostaglandins
176:
175:
173:
172:
165:
158:
150:
147:
146:
145:
144:
139:
138:
137:
124:
123:
119:
118:
117:
116:
111:
106:
105:
104:
99:
94:
89:
71:
70:
66:
65:
64:
63:
62:
61:
56:
46:
38:
37:
15:
9:
6:
4:
3:
2:
2678:
2667:
2664:
2663:
2661:
2646:
2643:
2641:
2638:
2636:
2633:
2631:
2628:
2627:
2625:
2623:
2619:
2613:
2610:
2609:
2607:
2605:
2604:Sphingolipids
2601:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2571:
2569:
2567:
2566:Phospholipids
2563:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2526:
2525:
2522:
2520:
2517:
2515:
2514:Monoglyceride
2512:
2511:
2509:
2507:
2503:
2497:
2494:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2476:Palmitic acid
2474:
2472:
2471:Myristic acid
2469:
2467:
2464:
2462:
2459:
2457:
2456:Caprylic acid
2454:
2453:
2451:
2449:
2445:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2415:
2413:
2411:
2407:
2401:
2398:
2396:
2393:
2391:
2388:
2386:
2383:
2382:
2380:
2376:
2370:
2367:
2365:
2361:
2358:
2356:
2353:
2351:
2348:
2346:
2343:
2341:
2338:
2336:
2335:Saturated fat
2332:
2329:
2328:
2326:
2322:
2318:
2310:
2305:
2303:
2298:
2296:
2291:
2290:
2287:
2275:
2272:
2270:
2267:
2265:
2262:
2260:
2257:
2255:
2252:
2250:
2249:Fortification
2247:
2245:
2242:
2240:
2237:
2235:
2232:
2230:
2227:
2225:
2224:Carbohydrates
2222:
2220:
2217:
2216:
2213:
2209:
2202:
2197:
2195:
2190:
2188:
2183:
2182:
2179:
2169:
2167:9780323551885
2163:
2159:
2158:
2150:
2139:
2132:
2125:
2117:
2113:
2108:
2103:
2099:
2095:
2091:
2084:
2076:
2072:
2068:
2065:(in French).
2064:
2057:
2049:
2045:
2041:
2037:
2033:
2026:
2018:
2014:
2010:
2006:
2002:
1998:
1991:
1983:
1979:
1974:
1969:
1964:
1959:
1955:
1951:
1947:
1943:
1939:
1932:
1925:
1921:
1918:
1913:
1902:
1898:
1891:
1885:
1874:
1870:
1863:
1857:
1846:
1842:
1838:
1833:
1828:
1825:(5): 581–97.
1824:
1820:
1813:
1806:
1798:
1794:
1789:
1784:
1780:
1776:
1772:
1768:
1764:
1757:
1749:
1745:
1741:
1737:
1733:
1729:
1722:
1715:
1711:
1707:
1702:
1697:
1692:
1687:
1683:
1679:
1675:
1671:
1667:
1660:
1653:
1649:
1645:
1641:
1637:
1633:
1629:
1626:(6): 659–62.
1625:
1621:
1614:
1605:
1600:
1596:
1592:
1588:
1581:
1573:
1571:9780367806323
1567:
1563:
1562:
1554:
1546:
1542:
1537:
1532:
1528:
1524:
1520:
1513:
1505:
1501:
1496:
1491:
1488:(4): 228–34.
1487:
1483:
1479:
1472:
1464:
1460:
1456:
1452:
1449:(3): 150–67.
1448:
1444:
1437:
1428:
1420:
1416:
1412:
1408:
1404:
1400:
1393:
1385:
1381:
1376:
1371:
1367:
1363:
1359:
1352:
1344:
1340:
1335:
1330:
1326:
1322:
1318:
1314:
1313:Mol Biol Evol
1310:
1303:
1301:
1292:
1288:
1283:
1278:
1274:
1270:
1266:
1262:
1258:
1251:
1243:
1239:
1234:
1229:
1226:(5): 559–79.
1225:
1221:
1217:
1210:
1201:
1196:
1192:
1188:
1187:J. Biol. Chem
1184:
1177:
1169:
1162:
1154:
1150:
1146:
1142:
1138:
1134:
1130:
1126:
1119:
1117:
1108:
1104:
1099:
1094:
1090:
1086:
1082:
1075:
1067:
1063:
1058:
1053:
1049:
1045:
1041:
1037:
1033:
1026:
1011:
1005:
1001:
1000:
992:
984:
978:
974:
969:
968:
959:
943:
937:
935:
933:
931:
926:
916:
913:
911:
908:
906:
903:
901:
898:
896:
893:
891:
888:
886:
883:
881:
878:
876:
873:
871:
868:
866:
863:
859:
856:
854:
853:Prostaglandin
851:
849:
846:
844:
841:
840:
839:
836:
835:
828:
826:
822:
818:
815:results in a
814:
805:
803:
799:
789:
786:
783:
782:Linoleic acid
780:
779:
775:
772:
769:
767:
763:
762:
758:
755:
752:
751:
748:
746:
736:
731:
721:
718:
714:
710:
706:
701:
698:
692:
690:
686:
681:
679:
675:
671:
667:
666:pumpkin seeds
663:
659:
655:
651:
647:
643:
639:
635:
631:
621:
617:
615:
611:
607:
602:
598:
595:
591:
587:
583:
579:
577:
567:
565:
561:
553:
550:
547:
544:
541:
538:
537:
535:
532:
527:
524:
521:
518:
517:
515:
512:
511:
510:
507:
505:
502:
498:
488:
487:linoleic acid
485:
484:
482:
479:
474:
471:
470:
468:
465:
464:
463:
460:
458:
454:
450:
446:
442:
430:
426:
425:
424:
418:
417:
408:
404:
400:
396:
388:
384:
381:chain plus a
380:
377:
371:
358:
354:
350:
347:
343:
339:
335:
331:
327:
323:
319:
315:
312:
308:
304:
301:
297:
294:
290:
286:
285:
283:
282:
281:
276:
266:
264:
260:
255:
253:
249:
245:
241:
236:
234:
230:
226:
222:
218:
214:
210:
206:
205:linoleic acid
202:
198:
194:
190:
186:
182:
171:
166:
164:
159:
157:
152:
151:
149:
148:
143:
140:
136:
133:
132:
131:
128:
127:
126:
125:
121:
120:
115:
112:
110:
107:
103:
100:
98:
95:
93:
90:
88:
85:
84:
82:
78:
75:
74:
73:
72:
68:
67:
60:
57:
55:
52:
51:
50:
47:
45:
44:Saturated fat
42:
41:
40:
39:
36:
32:
28:
27:
22:
21:essential oil
2645:Secosteroids
2640:Sex steroids
2529:Triheptanoin
2524:Triglyceride
2491:Behenic acid
2481:Stearic acid
2438:Leukotrienes
2428:Prostacyclin
2359:
2354:
2330:
2238:
2156:
2149:
2138:the original
2124:
2097:
2094:EFSA Journal
2093:
2083:
2066:
2062:
2056:
2039:
2035:
2025:
2000:
1996:
1990:
1945:
1941:
1931:
1912:
1896:
1884:
1868:
1856:
1822:
1818:
1805:
1770:
1766:
1756:
1731:
1727:
1721:
1713:
1673:
1669:
1659:
1651:
1623:
1619:
1613:
1594:
1591:EFSA Journal
1590:
1580:
1560:
1553:
1526:
1522:
1512:
1485:
1481:
1471:
1446:
1442:
1436:
1427:
1402:
1398:
1392:
1365:
1361:
1351:
1316:
1312:
1264:
1260:
1250:
1223:
1219:
1209:
1190:
1186:
1176:
1167:
1161:
1128:
1124:
1088:
1084:
1074:
1039:
1035:
1025:
1013:. Retrieved
998:
991:
966:
958:
946:. Retrieved
812:
811:
795:
765:
753:Common name
742:
733:
724:Human health
716:
712:
704:
702:
693:
689:osteoporosis
682:
642:flaxseed oil
627:
624:Food sources
618:
610:leukotrienes
603:
599:
593:
589:
588:
584:
580:
573:
562:
559:
508:
494:
461:
456:
452:
448:
444:
439:
415:
402:
387:methyl group
373:
326:isoprostanes
293:inflammation
287:the classic
279:
261:rather than
256:
237:
229:thromboxanes
225:leukotrienes
184:
180:
179:
109:Triglyceride
80:
2630:Cholesterol
2589:Cardiolipin
2549:Trilinolein
2539:Tripalmitin
2534:Trimyristin
2519:Diglyceride
2466:Lauric acid
2461:Capric acid
2448:Fatty acids
2433:Thromboxane
2410:Eicosanoids
2100:(7): 1176.
1597:(3): 1461.
858:Thromboxane
848:Leukotriene
497:synthesized
379:hydrocarbon
359:production)
346:lipid rafts
336:(EETs) and
322:neurofurans
291:(affecting
289:eicosanoids
189:fatty acids
114:Cholesterol
2544:Tristearin
2506:Glycerides
2331:Saturation
1443:Nutr Metab
1015:13 October
922:References
838:Eicosanoid
817:dermatitis
662:chia seeds
614:anandamide
501:desaturase
344:They form
330:hepoxilins
203:(ALA) and
77:Fatty acid
69:Components
2385:Trans fat
2315:Types of
2219:Additives
2116:1831-4732
1869:iupac.org
900:Oily fish
890:Krill oil
650:olive oil
646:hemp seed
634:shellfish
376:aliphatic
318:isofurans
311:resolvins
269:Functions
217:cofactors
135:Trans fat
29:Types of
2660:Category
2622:Steroids
2612:Ceramide
2554:Triolein
2378:Geometry
2269:Vitamins
2264:Proteins
2229:Coloring
2075:17091903
2048:17086218
2017:16919517
1920:Archived
1901:Archived
1873:Archived
1845:Archived
1841:16188209
1797:23076616
1648:25642190
1545:12934069
1419:19500961
1384:10479232
1343:28333262
1291:15736910
1242:16188208
1153:25945627
1145:16892270
1066:25328170
831:See also
787:Omega−6
773:Omega−3
747:(EFSA).
654:soya oil
638:flaxseed
436:Examples
357:cytokine
307:lipoxins
263:vitamins
233:lipoxins
2324:General
2244:Flavors
2234:Enzymes
1982:8127910
1950:Bibcode
1788:3497923
1748:9624425
1710:3097647
1678:Bibcode
1640:8646953
1504:1117180
1463:5001758
1334:5435082
1282:7101959
1107:6805293
1057:4190204
973:134–138
948:22 July
678:walnuts
594:de novo
504:enzymes
457:LC-PUFA
449:SC-PUFA
102:Omega−9
97:Omega−7
92:Omega−6
87:Omega−3
2317:lipids
2254:Lipids
2164:
2114:
2073:
2046:
2015:
1980:
1970:
1839:
1795:
1785:
1746:
1708:
1701:387103
1698:
1646:
1638:
1568:
1543:
1502:
1461:
1417:
1382:
1341:
1331:
1289:
1279:
1261:Lipids
1240:
1151:
1143:
1105:
1064:
1054:
1006:
979:
770:(ALA)
676:, and
187:, are
2360:Other
2274:Water
2141:(PDF)
2134:(PDF)
1973:43279
1904:(PDF)
1893:(PDF)
1876:(PDF)
1865:(PDF)
1848:(PDF)
1815:(PDF)
1644:S2CID
1149:S2CID
790:10 g
784:(LA)
766:alpha
756:Type
697:algae
353:NF-κB
183:, or
2162:ISBN
2112:ISSN
2071:PMID
2044:PMID
2013:PMID
1978:PMID
1837:PMID
1793:PMID
1744:PMID
1706:PMID
1636:PMID
1566:ISBN
1541:PMID
1500:PMID
1459:PMID
1415:PMID
1380:PMID
1339:PMID
1287:PMID
1238:PMID
1141:PMID
1103:PMID
1062:PMID
1017:2010
1004:ISBN
977:ISBN
950:2024
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