Editing Essential fatty acid

{{Short description|Fatty acids required for biological processes}}
{{Distinguish|essential oil}}
{{Fats}}

'''Essential fatty acids''', or '''EFAs''', are [[fatty acid]]s that are required by humans and other animals for normal [[physiology|physiological functio]]n that cannot be [[Biosynthesis|synthesized in the body]].<ref name="ods">{{cite web |title=Omega-3 Fatty Acids |url=https://ods.od.nih.gov/factsheets/Omega3FattyAcids-HealthProfessional/ |publisher=Office of Dietary Supplements, US National Institutes of Health |access-date=22 July 2024 |date=15 February 2023}}</ref><ref>{{cite book | title = Modern Nutrition in Health and Disease | edition = 6th | year = 1980 | author1 = Robert S. Goodhart | author2 = Maurice E. Shils | publisher = Lea and Febinger | location = Philadelphia | isbn = 978-0-8121-0645-9 | pages = [https://archive.org/details/modernnutritionie6shil/page/134 134–138] | url-access = registration | url = https://archive.org/details/modernnutritionie6shil/page/134 }}</ref>⁠ As they are not  synthesized in the body, the essential fatty acids {{ndash}} [[alpha-linolenic acid]] (ALA) and [[linoleic acid]] {{ndash}} must be obtained from food or from a [[dietary supplement]].<ref name=ods/><ref name="VaughanGeissler2009">{{cite book| first1 = John Griffith | last1 = Vaughan | first2 = Catherine | last2 = Geissler| first3 = Barbara | last3 = Nicholson | first4 = Elisabeth | last4 = Dowle | first5 = Elizabeth | last5 = Rice | name-list-style = vanc |title=The new Oxford book of food plants|url=https://archive.org/details/the-new-oxford-book-of-food-plants-2009-john-vaughan-catherine-geissler/page/212/mode/1up|access-date=13 October 2010|year=2009|publisher=Oxford University Press US|isbn=978-0-19-954946-7|pages=212–235}}</ref><ref name="kaur">{{cite journal |vauthors=Kaur N, Chugh V, Gupta AK |title=Essential fatty acids as functional components of foods- a review |journal=Journal of Food Science and Technology |volume=51 |issue=10 |pages=2289–303 |date=October 2014 |pmid=25328170 |pmc=4190204 |doi=10.1007/s13197-012-0677-0}}</ref> Essential fatty acids are needed for various cellular [[metabolic process]]es and for the maintenance and function of tissues and organs.<ref name=ods/><ref name="AJCN">{{cite journal | vauthors = Chipponi JX, Bleier JC, Santi MT, Rudman D | title = Deficiencies of essential and conditionally essential nutrients | journal = The American Journal of Clinical Nutrition | volume = 35 | issue = 5 Suppl | pages = 1112–6 | date = May 1982 | pmid = 6805293 | doi = 10.1093/ajcn/35.5.1112 | doi-access = free }}</ref> These fatty acids also are precursors to vitamins, [[Cofactor (biochemistry)|cofactors]], and derivatives, including [[prostaglandin]]s, [[leukotriene]]s, [[thromboxane]]s, [[lipoxin]]s, and others.<ref name=Das/>

Only two fatty acids are known to be essential for humans: alpha-linolenic acid (an [[omega-3 fatty acid|omega−3 fatty acid]]) and linoleic acid (an [[omega-6 fatty acid|omega−6 fatty acid]]). These are supplied to the body either as the free fatty acid, or more commonly as some glyceride derivative.<ref>{{cite book |author1=Whitney Ellie |author2=Rolfes SR | title = Understanding Nutrition | edition = 11th | location = California | publisher = Thomson Wadsworth | year = 2008 | pages = 154}}</ref> ALA can be converted into [[eicosapentaenoic acid]] and [[docosahexaenoic acid]], but the conversion amount is small, requiring intake from food or supplements.<ref name=ods/> Deficiency in omega−3 fatty acids is very common. The average American has a dietary ratio between omega−6 fatty acids and omega−3 fatty acids of 20:1.

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 [[fat]]s rather than [[vitamin]]s.<ref name=Burr>{{cite journal| vauthors=Burr GO, Burr MM| date=April 1930| title=On the nature and role of the fatty acids essential in nutrition| journal=J. Biol. Chem.| volume=86| issue=2| pages=587–621| doi=10.1016/S0021-9258(20)78929-5| doi-access=free}}</ref>

==Functions==
{{For|the biological effects of the ω−3 and ω−6 fatty acids which are mediated by their mutual interactions|Essential fatty acid interactions}}
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.
* They are modified to make
** the classic [[eicosanoid]]s (affecting [[inflammation]] and many other cellular functions)
** the [[Cannabinoid#Endocannabinoids|endocannabinoids]] (affecting mood, behavior and inflammation)
** the [[lipoxin]]s which are a group of eicosanoid derivatives formed via the lipoxygenase pathway from ω−6 EFAs and [[resolvins]] from ω−3 (in the presence of acetylsalicylic acid, downregulating inflammation)
** the [[isofuran]]s, [[neurofuran]]s, [[isoprostane]]s, [[hepoxilin]]s, [[epoxyeicosatrienoic acid]]s (EETs) and [[Neuroprotectin|neuroprotectin D]]
* They form [[lipid raft]]s (affecting cellular signaling)<ref name="WStillwell">{{cite journal |vauthors=Stillwell W, Shaikh SR, Zerouga M, Siddiqui R, Wassall SR |title=Docosahexaenoic acid affects cell signaling by altering lipid rafts |journal=Reproduction, Nutrition, Development |volume=45 |issue=5 |pages=559–79 |year=2005 |pmid=16188208 |doi=10.1051/rnd:2005046|url=https://hal.archives-ouvertes.fr/hal-00900583/document |doi-access=free }}</ref>
* They act on DNA (activating or inhibiting transcription factors such as [[NF-κB]], which is linked to pro-inflammatory [[cytokine]] production)<ref name="PCalder">{{cite journal |author=Calder PC |title=n-3 fatty acids, inflammation, and immunity--relevance to postsurgical and critically ill patients |journal=Lipids |volume=39 |issue=12 |pages=1147–61 |date=December 2004 |pmid=15736910 |doi=10.1007/s11745-004-1342-z|pmc=7101959 }}</ref>

==Nomenclature and terminology==
{{Main|Fatty acid#Nomenclature}}
Fatty acids comprise an [[aliphatic]] [[hydrocarbon]] chain plus a [[carboxyl group]] (–COOH) at one end, and terminated by a [[methyl group]] (–CH<sub>3</sub>) 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 "[[omega|ω]]", the last letter in the [[Greek alphabet]]. In the expression ''ω−x'', 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 [[stearidonic acid]], an 18-carbon chain with 4 double bonds, and with a double bond between the third and fourth carbon atoms from the CH<sub>3</sub> end. Double bonds are [[geometric isomerism|''cis'']] and separated by a single methylene (CH<sub>2</sub>) group unless otherwise noted. In free fatty acid form, the chemical structure of stearidonic acid is:
:[[Image:Fatty acid carbon numbering.svg|500px|Chemical structure of [[stearidonic acid]] showing physiological (red) and chemical (blue) numbering conventions]]{{clear left}}

===Examples===
[[Polyunsaturated fatty acid]]s with 16- and 18-carbon chains are sometimes classified as '''short chain polyunsaturated fatty acids''' ('''SC-PUFA'''), as opposed to '''long-chain polyunsaturated fatty acids''' ('''LC-PUFA'''), which have more than 18 carbon atoms.<ref name=PUFA>{{cite journal |vauthors=Buckley MT et al. |title=Selection in Europeans on Fatty Acid Desaturases Associated with Dietary Changes |journal=Mol Biol Evol |volume=34 |issue=6 |pages=1307–1318 |year=2017 |pmid=28333262 |pmc=5435082 |doi=10.1093/molbev/msx103}}</ref>

Both the essential fatty acids are SC-PUFA with an 18-carbon chain:
* [[omega-3 fatty acid|ω−3 fatty acid]]:
** [[alpha-linolenic acid|α-linolenic acid]] or ALA (18:3n−3)
* [[Omega-6 fatty acid|ω−6 fatty acid]]:
** [[linoleic acid]] or LA (18:2n−6)
These two fatty acids cannot be [[Biosynthesis|synthesized]] by humans because humans lack the [[desaturase]] [[enzymes]] required for their production.

They form the starting point for the creation of more desaturated fatty acids, most of which also have a longer carbon chain:
* [[omega-3 fatty acid|ω−3 fatty acid]]s:
** [[eicosapentaenoic acid]] or EPA (20:5n−3)
** [[docosahexaenoic acid]] or DHA (22:6n−3)
* [[Omega-6 fatty acid|ω−6 fatty acids]]:
** [[gamma-linolenic acid]] or GLA (18:3n−6)
** [[dihomo-gamma-linolenic acid]] or DGLA (20:3n−6)
** [[arachidonic acid]] or AA (20:4n−6)
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.<ref name=PUFA />

[[Omega-9 fatty acid|ω−9 fatty acids]] are not essential in humans because they can be synthesized from carbohydrates or other fatty acids.

==Essentiality in human diet==
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 [[alpha-linolenic acid]] (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.<ref>{{cite journal |doi=10.1093/ajcn/70.3.560s|title=Essential fatty acids in health and chronic disease |year=1999 |last1=Simopoulos |first1=Artemis P. |journal=The American Journal of Clinical Nutrition |volume=70 |issue=3 |pages=560s–569s |pmid=10479232 |doi-access=free }}</ref><ref name=Das>{{cite journal |doi=10.1002/biot.200600012|title=Essential Fatty Acids: Biochemistry, Physiology and Pathology |year=2006 |last1=Das |first1=Undurti N. |journal=Biotechnology Journal |volume=1 |issue=4 |pages=420–439 |pmid=16892270 |s2cid=25945627 }}</ref>

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 lower blood levels of DHA than through direct ingestion. This is illustrated by studies in vegans and vegetarians.<ref>{{cite journal | vauthors = Sanders TA | year = 2009 | title = DHA Status of vegetarians | journal = Prostaglandins Leukotrienes Essential Fatty Acids | volume = 81 | issue = 2–3| pages = 137–41 | doi = 10.1016/j.plefa.2009.05.013 | pmid = 19500961 }}</ref> 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.

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 newborn infant. Many infant formulas have AA and DHA added to them with an aim to make them more equivalent to human milk.{{Citation needed|date=April 2025}}

''Essential nutrients'' are defined as those that cannot be synthesized ''de novo'' in sufficient quantities for normal physiological function. This definition is met for LA and ALA but not the longer chain derivatives in adults.<ref>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</ref> The longer chain derivatives particularly, however, have pharmacological properties that can modulate disease processes, but this should not be confused with dietary essentiality.

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 skin symptoms.<ref>{{cite journal | pmid = 5001758 | volume=13 | issue=3 | title=Plasma lipids in human linoleic acid deficiency. | year=1971 | journal=Nutr Metab | pages=150–67 | doi=10.1159/000175332 | vauthors=Collins FD, Sinclair AJ, Royle JP, Coats DA, Maynard AT, Leonard RF}}</ref> This could be treated by infusing lipids, and later studies showed that topical application of sunflower oil would also resolve the dermal symptoms.<ref>{{cite journal | last1 = Prottey | first1 = C | last2 = Hartop | first2 = PJ | last3 = Press | first3 = M | year = 1975 | title = Correction of the cutaneous manifestations of essential fatty acid deficiency in man by application of sunflower-seed oil to the skin.| journal = J Invest Dermatol | volume = 64 | issue = 4| pages = 228–34 | pmid = 1117180 | doi=10.1111/1523-1747.ep12510667| doi-access = free }}</ref> 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.

The main physiological requirement for ω−6 fatty acids is attributed to [[arachidonic acid]], which is the major precursor of [[prostaglandins]], [[leukotrienes]] that play a vital role in cell signaling, and an endogenous cannabinoid [[anandamide]].<ref>{{cite journal|title=The endocannabinoid system, anandamide and the regulation of mammalian cell apoptosis|first1=M|last1=Maccarrone|first2=A|last2=Finazzi-Agró|date=22 August 2003|journal=Cell Death & Differentiation|volume=10|issue=9|pages=946–955|doi=10.1038/sj.cdd.4401284|pmid=12934069|doi-access=free}}</ref> Metabolites from the ω−3 pathway, mainly from eicosapentaenoic acid, are mostly inactive.<ref>{{cite book |last1=Sanders |first1=Tom |last2=Emery |first2=Peter |url=https://books.google.com/books?id=M9sCyAEACAAJ |publisher=Taylor Frances |location=London |title=Molecular Basis of Human Nutrition |isbn=9780367806323 |year=2003 }}</ref>

Reviews by the European Food Safety Authority<ref>{{cite journal | last1 = Jones | first1 = A | year = 2010 | title = EFSA Scientific Opinion on Dietary Reference Values for fats, including saturated fatty acids, polyunsaturated fatty acids, monounsaturated fatty acids, trans fatty acids and cholesterol | journal = EFSA Journal | volume = 8 | issue = 3| page = 1461 | doi = 10.2903/j.efsa.2010.1461 | doi-access = free }}</ref> 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.<ref name=Nugent>{{cite journal |vauthors=Nugent KP, Spigelman AD, Phillips RK |title=Tissue prostaglandin levels in familial adenomatous polyposis patients treated with sulindac |journal=Diseases of the Colon and Rectum |volume=39 |issue=6 |pages=659–62 |date=June 1996 |pmid=8646953 |quote=Arachidonic acid is an essential fatty acid... |doi=10.1007/BF02056946|s2cid=25642190 }}</ref><ref name=Carlstedt>{{cite journal |vauthors=Carlstedt-Duke J, Brönnegård M, Strandvik B |title=Pathological regulation of arachidonic acid release in cystic fibrosis: the putative basic defect |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=83 |issue=23 |pages=9202–6 |date=December 1986 |pmid=3097647 |pmc=387103 |doi=10.1073/pnas.83.23.9202 |quote=[T]he turnover of essential fatty acids is increased (7). Arachidonic acid is one of the essential fatty acids affected.|bibcode=1986PNAS...83.9202C |doi-access=free }}</ref>

==Food sources==

Some of the food sources of ω−3 and ω−6 fatty acids are [[fish]] and [[shellfish]], seaweed oil, [[flax]]seed (linseed) and [[flaxseed oil]], [[hemp seed]], [[olive oil]], [[soybean oil|soya oil]], [[canola oil|canola (rapeseed) oil]], [[salvia hispanica|chia seeds]], [[pumpkin seed]]s, [[sunflower seeds]], [[leafy vegetable]]s, and [[walnut]]s.

Essential fatty acids play a part in many [[metabolism|metabolic processes]], 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 [[osteoporosis]].<ref>{{cite journal |vauthors=Kruger MC, Horrobin DF |title=Calcium metabolism, osteoporosis and essential fatty acids: a review |journal=Progress in Lipid Research |volume=36 |issue=2–3 |pages=131–51 |date=September 1997 |pmid=9624425 |doi=10.1016/S0163-7827(97)00007-6}}</ref>

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 have a modest benefit for cardiovascular health.<ref>{{cite journal |vauthors=Pan A, Chen M, Chowdhury R |title=α-Linolenic acid and risk of cardiovascular disease: a systematic review and meta-analysis |journal=Am. J. Clin. Nutr. |volume=96 |issue=6 |pages=1262–73 |date=December 2012  |pmid=23076616 |pmc=3497923 |doi=10.3945/ajcn.112.044040 |type=Systematic review|display-authors=etal}}</ref> The human body can (and in case of a purely vegetarian diet often must unless certain [[algae]] or supplements derived from them are consumed) convert ALA to EPA and subsequently DHA. The conversion of ALA to DHA is sufficient in the adult and additional DHA is not required in the diet.<ref name=":0">{{Cite journal |last1=Domenichiello |first1=Anthony F. |last2=Kitson |first2=Alex P. |last3=Bazinet |first3=Richard P. |date=July 2015 |title=Is docosahexaenoic acid synthesis from α-linolenic acid sufficient to supply the adult brain? |url=https://linkinghub.elsevier.com/retrieve/pii/S0163782715000223 |journal=Progress in Lipid Research |language=en |volume=59 |pages=54–66 |doi=10.1016/j.plipres.2015.04.002|pmid=25920364 |doi-access=free }}</ref> In the infant, the case is less clear; preformed DHA may be required in breastmilk or formula for adequate development, as DHA supplementation in formula was found to improve cognitive development up to one year of age.<ref name=":0" /> The effects of DHA supplementation in early childhood after one year are unclear.<ref name=":0" />

The ''IUPAC Lipid Handbook'' provides a very large and detailed listing of fat contents of animal and vegetable fats, including ω−3 and −6 oils.<ref>{{cite web|url=http://www.iupac.org/publications/pac/2001/pdf/7304x0685.pdf|title=IUPAC Lipid Handbook|website=iupac.org|url-status=live|archive-url=https://web.archive.org/web/20060212173746/http://www.iupac.org/publications/pac/2001/pdf/7304x0685.pdf|archive-date=2006-02-12}}</ref> The [[National Institutes of Health]]'s EFA Education group publishes ''Essential Fats in Food Oils''.<ref>{{cite web|url=http://efaeducation.org/Bal_pdfs/FatsOils.pdf|title=Essential Fats in Food Oils|website=efaeducation.org|url-status=live|archive-url=https://web.archive.org/web/20141210062034/http://efaeducation.org/Bal_pdfs/FatsOils.pdf|archive-date=2014-12-10}}</ref> This lists 40 common oils, more tightly focused on EFAs and sorted by n−6:3 ratio. ''Vegetable Lipids as Components of Functional Food'' lists notable vegetable sources of EFAs as well as commentary and an overview of the biosynthetic pathways involved.<ref>[http://publib.upol.cz/~obd/fulltext/Biomedic146-2/LF11_2002-1.pdf Vegetable Lipids as Components of Functional Food] {{webarchive|url=https://web.archive.org/web/20060320003053/http://publib.upol.cz/~obd/fulltext/Biomedic146-2/LF11_2002-1.pdf |date=2006-03-20 }}, Stuchlik and Zak</ref> 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 that the EFA makeup varies markedly with fats from different body parts.

==Human health==
{{Main|Diet and heart disease}}
Essential fatty acids play an important role in the life and death of cardiac cells.<ref>{{cite journal |vauthors=Honoré E, Barhanin J, Attali B, Lesage F, Lazdunski M |title=External blockade of the major cardiac delayed-rectifier K+ channel (Kv1.5) by polyunsaturated fatty acids |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=91 |issue=5 |pages=1937–41 |date=March 1994 |pmid=8127910 |pmc=43279 |doi=10.1073/pnas.91.5.1937|bibcode=1994PNAS...91.1937H |doi-access=free }}</ref><ref>{{cite journal |vauthors=Reiffel JA, McDonald A |title=Antiarrhythmic effects of omega-3 fatty acids |journal=The American Journal of Cardiology |volume=98 |issue=4A |pages=50i–60i |date=August 2006 |pmid=16919517 |doi=10.1016/j.amjcard.2005.12.027}}</ref><ref>{{cite journal |vauthors=Landmark K, Alm CS |title=[Alpha-linolenic acid, cardiovascular disease and sudden death] |language=no |journal=Tidsskrift for den Norske Lægeforening |volume=126 |issue=21 |pages=2792–4 |date=November 2006 |pmid=17086218 |url=http://www.tidsskriftet.no/index.php?seks_id=1446845}}</ref><ref>{{cite journal |author=Herbaut C |title=[Omega-3 and health] |language=fr |journal=Revue Médicale de Bruxelles |volume=27 |issue=4 |pages=S355–60 |date=September 2006 |pmid=17091903}}</ref> 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).

=== Reference intake values ===
Reference intake values for as published by the Panel on Dietetic Products, Nutrition and Allergies of the [[European Food Safety Authority]] (EFSA).<ref>{{Cite journal|last=European Food Safety Authority (EFSA)|date=2009-07-01|title=Labelling reference intake values for n-3 and n-6 polyunsaturated fatty acids|journal=EFSA Journal|language=en|volume=7|issue=7|page=1176|doi=10.2903/j.efsa.2009.1176|issn=1831-4732|doi-access=free}}</ref>
{| class="wikitable"
!Common name
!Type
!Reference intake values
|-
|[[Alpha-Linolenic acid|''alpha''-Linolenic acid]] (ALA)
|Omega−3
|2 g
|-
|[[Linoleic acid]] (LA)
|Omega−6
|10 g
|}

In the United States, the [[Dietary Reference Intake|Adequate Intake]] (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 [[Dietary Reference Intake|Estimated Average Requirement]] (EAR) for either.<ref>{{cite web|url=https://www.nal.usda.gov/sites/default/files/fnic_uploads/energy_full_report.pdf|archive-url=https://web.archive.org/web/20220627114710/https://www.nal.usda.gov/sites/default/files/fnic_uploads/energy_full_report.pdf|archive-date = 2022-06-27|title=DIETARY REFERENCE INTAKES for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids|author=Food and Nutrition Board|year=2004|pages=422–514}}</ref>

===Essential fatty acid deficiency===
''Essential fatty acid deficiency'' results in a [[dermatitis]] similar to that seen in [[zinc deficiency|zinc]] or [[biotin deficiency]].<ref name="Andrews">{{cite book |url=https://books.google.com/books?id=UEaEDwAAQBAJ&pg=PA482 |page=482 |title=Andrews' Diseases of the Skin: Clinical Dermatology |isbn=9780323551885 |last1=James |first1=William D. |last2=Elston |first2=Dirk |last3=Treat |first3=James R. |last4=Rosenbach |first4=Misha A. |last5=Neuhaus |first5=Isaac |date=2019-01-18 |publisher=Elsevier Health Sciences }}</ref>

==See also==
{{col div|colwidth=20em}}
* [[Eicosanoid]]
** [[Hydroxyeicosatetraenoic acid]]
** [[Leukotriene]]
** [[Prostaglandin]]
** [[Thromboxane]]
* [[Specialized proresolving mediators]]
* [[Essential amino acid]]
* [[Essential fatty acid interactions]]
* [[Fatty acid metabolism]]
* [[Fatty acid synthase]]
* [[Krill oil]]
* [[Nonclassic eicosanoid]]
* [[Oily fish]]
* [[Omega-3 fatty acid|Omega−3 fatty acid]]
* [[Omega-6 fatty acid|Omega−6 fatty acid]]
* [[Polyunsaturated fat]]
{{colend}}

==References==
{{Reflist|30em}}

{{Food chemistry}}
{{Lipids}}
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[[Category:Essential fatty acids| ]]