Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Linoleic acid: Difference between pages

{{short description|Polyunsaturated omega-6 fatty acid}}

{{Distinguish|linolenic acid|alpha-linolenic acid|lipoic acid|linolelaidic acid}}

{{Use dmy dates|date=August 2020}}

| verifiedrevid = 476999843

| Name = Linoleic acid

| ImageFile = LAnumbering.png

| ImageSize = 300px

| ImageFile1 = Linoleic-acid-from-xtal-1979-3D-balls.png

| ImageSize1 = 300px

| ImageFile2 = Linoleic-acid-from-xtal-1979-3D-vdW.png

| ImageSize2 = 300px

| PIN = (9''Z'',12''Z'')-Octadeca-9,12-dienoic acid

| OtherNames = ''cis'',''cis''-9,12-Octadecadienoic acid<br>C18:2 ([[Fatty acid#Nomenclature|Lipid numbers]])

| IUPHAR_ligand = 1052

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| Gmelin = 57557

| Beilstein = 1727101

| PubChem = 5280450

| EC_number = 200-470-9

| DrugBank = DB14104

| 3DMet = B00328

| UNII = 9KJL21T0QJ

| ChEBI_Ref = {{ebicite|correct|EBI}}

| C=18 | H=32 | O=2

| Appearance = Colorless oil

| Density = 0.9 g/cm³<ref name=Merck>''The [[Merck Index]]'', 11th Edition, '''5382'''</ref>

| MeltingPt = {{convert|-12|C|F}}<ref name=Merck/><br/>{{convert|-6.9|C|F}}<ref name="crc97">{{cite book | author=William M. Haynes | title=CRC Handbook of Chemistry and Physics | edition=97th | year=2016 | publisher=CRC Press | location=Boca Raton | isbn=978-1-4987-5429-3 | pages=3–338 | url=https://books.google.com/books?id=VVezDAAAQBAJ}}</ref><br/>{{convert|-5|C|F}}<ref name=GESTIS>{{GESTIS|ZVG=14230|CAS=60-33-3}}</ref>

| BoilingPt = {{convert|229|C|F}} at 16 mmHg<ref name="crc97"/><br/>{{convert|230|C|F}} at 21 mbar<ref name=GESTIS/><br/>{{convert|230|C|F}} at 16 mmHg<ref name=Merck/>

| Solubility = 0.139 mg/L<ref name=GESTIS/>

| VaporPressure = 16 Torr at 229&nbsp;°C{{Citation needed|date=June 2011}}

| pKa = 4.77 at 25°C<ref name=pubchem>National Center for Biotechnology Information (2024). PubChem Compound Summary for CID 5280450, Linoleic Acid. Retrieved January 20, 2024 from https://pubchem.ncbi.nlm.nih.gov/compound/Linoleic-Acid.</ref>

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

| MainHazards =

| FlashPt = {{convert|112|C|F}}<ref name=GESTIS/>

| AutoignitionPt = }}

| Section4 =

| Section5 =

| Section6 =

'''Linoleic acid''' ('''LA''') is an [[organic compound]] with the formula {{chem2|HOOC(CH2)7CH\dCHCH2CH\dCH(CH2)4CH3}}. Both [[alkene]] groups ({{chem2|\sCH\dCH\s}}) are [[cis-trans isomerism|''cis'']]. It is a [[fatty acid]] sometimes denoted 18:2 (n-6) or 18:2 ''cis''-9,12. A '''linoleate''' is a [[salt (chemistry)|salt]] or [[ester]] of this acid.<ref>{{cite web|url=http://www.cyberlipid.org/fa/acid0001.htm|title=Fatty Acids|publisher=Cyber Lipid|access-date=31 July 2017|archive-url=https://web.archive.org/web/20181028011853/http://www.cyberlipid.org/fa/acid0001.htm|archive-date=28 October 2018|url-status=dead}}</ref>

Linoleic acid is a [[polyunsaturated fatty acid|polyunsaturated]], [[omega-6 fatty acid]]. It is a colorless liquid that is virtually [[insoluble]] in water but soluble in many [[organic solvent]]s.<ref name="crc97"/> It typically occurs in nature as a [[triglyceride]] (ester of [[glycerol|glycerin]]) rather than as a [[free fatty acid]].<ref name="Is there a fatty acid taste">{{cite journal| pmc=2843518 | pmid=19400700 | doi=10.1146/annurev-nutr-080508-141108 | volume=29 | title=Is there a fatty acid taste? | year=2009 | journal=[[Annual Review of Nutrition]] | pages=305–327 | last1=Mattes | first1=Richard D.}}</ref> It is one of two [[essential fatty acid]]s for humans, who must obtain it through their diet,<ref>{{cite journal|title=The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases|author=Simopoulos, Artemis P.|journal=Experimental Biology and Medicine|year=2008|volume=233|issue=6

| pages=674–688 | doi=10.3181/0711-mr-311 | pmid=18408140 |s2cid=9044197}}</ref> and the most essential, because the body uses it as a base to make the others.

The word "linoleic" derives {{ety|la|linum|[[flax]]||oleum|oil}}, reflecting the fact that it was first isolated from [[linseed oil]].

==History==

In 1844, [[F. Sacc]], working at the laboratory of [[Justus von Liebig]], isolated linoleic acid from linseed oil.<ref name=sacc1844/><ref name=sacc1845/> In 1886, [[K. Peters]] determined the existence of two double bonds.<ref name=mona1887>(1886), ''Monatsch''., volume 7, pages 522-</ref> Its essential role in human diet was discovered by [[G. O. Burr]] and others in 1930.<ref name=burr1930/> Its chemical structure was determined by [[T.P. Hilditch]] and others in 1939, and it was synthesized by R. A. Raphael and F. Sondheimer in 1950.<ref name=raph1950/>

==In physiology==

{{Main|Fatty acid desaturase|Fatty acid synthesis}}

The consumption of linoleic acid is vital to proper health, as it is an essential fatty acid.<ref name="Whelan & Fritsche">{{cite journal |last1=Whelan |first1=Jay |last2=Fritsche |first2=Kevin |title=Linoleic Acid |journal=Advances in Nutrition |date=May 2013 |volume=4 |issue=3 |pages=311–312 |doi=10.3945/an.113.003772|pmc=3650500 |pmid=23674797}}</ref>

===Metabolism and eicosanoids===

[[File:Linoleic Acid Metabolism.gif]]{{clear-left}}

Linoleic acid (LA: {{chem|[[Carbon|C]]|18|[[Hydrogen|H]]|32|[[Oxygen|O]]|2}}; 18:[[Double bond|2]], [[Omega-6 fatty acid|ω-6]]) is a precursor to [[arachidonic acid]] (AA: {{chem|C|20|H|32|O|2}}; 20:[[Double bond|4]], ω-6) with elongation and unsaturation.{{r|Whelan & Fritsche}} AA is the precursor to some [[prostaglandin]]s,<ref>{{cite journal |pmid=4723909 |date=25 August 1973 |last1=Wlodawer |first1=Paulina |last2=Samuelsson |first2=Bengt |title=On the organization and mechanism of prostaglandin synthetase |journal=The Journal of Biological Chemistry |volume=248 |issue=16 |pages=5673–5678 |doi=10.1016/S0021-9258(19)43558-8 |doi-access=free}}</ref> [[leukotriene]]s (LTA, LTB, LTC), [[thromboxane]] (TXA)<ref>{{cite journal |last1=Terano |first1=Takashi |last2=Salmon |first2=John A. |last3=Moncada |first3=Salvador |date=February 1984 |title=Biosynthesis and biological activity of leukotriene B5 |journal=Prostaglandins |volume=27 |issue=2 |pages=217–232 |doi=10.1016/0090-6980(84)90075-3 |pmid=6326200}}</ref> and the [[N-Acylethanolamine|N-acylethanolamine]] (NAE) [[Anandamide|arachidonoylethanolamine]] (AEA: {{chem|C|22|H|37|[[Biological functions of nitric oxide|NO]]|2}}; 20:4, [[Omega-6 fatty acid|ω-6]]),<ref>{{Cite journal |last1=Murru |first1=Elisabetta |last2=Lopes |first2=Paula A. |last3=Carta |first3=Gianfranca |last4=Manca |first4=Claudia |last5=Abolghasemi |first5=Armita |last6=Guil-Guerrero |first6=José L. |last7=Prates |first7=José A. M. |last8=Banni |first8=Sebastiano |date=2021-02-15 |title=Different Dietary N-3 Polyunsaturated Fatty Acid Formulations Distinctively Modify Tissue Fatty Acid and N-Acylethanolamine Profiles |journal=Nutrients |language=en |volume=13 |issue=2 |pages=625 |doi=10.3390/nu13020625 |pmid=33671938 |pmc=7919039 |issn=2072-6643|doi-access=free }}</ref> and other [[Endocannabinoid system|endocannabinoids]] and [[Eicosanoid|eicosanoids]].<ref>{{Cite journal |last1=Salem |first1=Norman |last2=Van Dael |first2=Peter |date=2020-02-27 |title=Arachidonic Acid in Human Milk |journal=Nutrients |language=en |volume=12 |issue=3 |pages=626 |doi=10.3390/nu12030626 |pmid=32121018 |pmc=7146261 |issn=2072-6643|doi-access=free }}</ref>

The metabolism of LA to AA begins with the conversion of LA into [[gamma-Linolenic acid|gamma-linolenic acid]] (GLA), effected by [[Fatty acid desaturase|Δ6-desaturase]].<ref name="David F. Horrobin 1993">Evidence suggests that infants must acquire Δ6-desaturase breast milk. Breast-milk fed babies have higher concentrations of GLA than formula-fed babies, while formula-fed babies have elevated concentrations of LA. {{cite journal | author = David F. Horrobin | year = 1993 | title = Fatty acid metabolism in health and disease: the role of Δ-6-desaturase | journal = American Journal of Clinical Nutrition | volume = 57 | issue = 5 Suppl | pages = 732S–737S| doi = 10.1093/ajcn/57.5.732S | pmid = 8386433 | doi-access = free }}</ref> GLA is converted to [[dihomo-γ-linolenic acid]] (DGLA), the immediate precursor to AA.

LA is also converted by various [[lipoxygenase]]s, [[cyclooxygenase]]s, [[cytochrome P450]] enzymes (the CYP [[monooxygenase]]s), and non-enzymatic [[autoxidation]] mechanisms to mono-[[Hydroxy group|hydroxyl]] products viz., [[13-Hydroxyoctadecadienoic acid]], and [[9-Hydroxyoctadecadienoic acid]]; these two hydroxy metabolites are enzymatically oxidized to their keto metabolites, 13-oxo-octadecadienoic acid and 9-oxo-octadecdienoic acid. Certain cytochrome P450 enzymes, the CYP [[epoxygenase]]s, catalyze oxidation of LA to epoxide products viz., its 12,13-epoxide, [[vernolic acid]], and its 9,10-epoxide, [[coronaric acid]]. These linoleic acid products are implicated in human physiology and pathology.<ref>{{Cite journal|last=Jandacek|first=Ronald J.|date=2017-05-20|title=Linoleic Acid: A Nutritional Quandary|journal=Healthcare|volume=5|issue=2|page=25|doi=10.3390/healthcare5020025|issn=2227-9032|pmc=5492028|pmid=28531128|doi-access=free}}</ref>

[[Hydroperoxide]]s derived from the metabolism of [[anandamide]] (AEA: {{chem|C|22|H|37|[[Biological functions of nitric oxide|NO]]|2}}; 20:4,n-6), or its [[Linoleyl alcohol|linoleoyl]] analogues, are by a [[lipoxygenase]] action found to be competitive inhibitors of [[brain]] and [[White blood cell|immune cell]] [[Fatty acid amide hydrolase|FAAH]], the [[enzyme]] that breaks down AEA and other endocannabinoids, and the compound linoleoyl-ethanol-amide ({{chem|C|20|H|37|NO|2}}; 18:2,n-6), an [[N-Acylethanolamine|N-acylethanolamine]],{{clarify|reason=Style of this sentence makes it incomprehensible to the reader. It needs to be reworded.|date=February 2023}} - the [[ethanolamide]] of linoleic acid (LA: {{chem|C|18|H|32|O|2}}; 18:[[Double bond|2]], [[Omega-6 fatty acid|n-6]]) and its metabolized incorporated [[ethanolamine]] (MEA: {{chem|C|2|H|7|NO}}),<ref>{{Cite web |last=PubChem |title=Linoleoyl ethanolamide |url=https://pubchem.ncbi.nlm.nih.gov/compound/5283446 |access-date=2022-10-29 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> is the first natural inhibitor of FAAH, discovered.<ref>{{Cite journal |last1=Maccarrone |first1=Mauro |last2=Stelt |first2=Marcelis van der |last3=Rossi |first3=Antonello |last4=Veldink |first4=Gerrit A. |last5=Vliegenthart |first5=Johannes F. G. |last6=Agrò |first6=Alessandro Finazzi |date=1998-11-27 |title=Anandamide Hydrolysis by Human Cells in Culture and Brain * |url=https://www.jbc.org/article/S0021-9258(19)59084-6/abstract |journal=Journal of Biological Chemistry |language=English |volume=273 |issue=48 |pages=32332–32339 |doi=10.1074/jbc.273.48.32332 |issn=0021-9258 |pmid=9822713|doi-access=free |hdl=1887/50863 |hdl-access=free }}</ref><ref>{{Cite journal |last1=Scala |first1=Coralie Di |last2=Fantini |first2=Jacques |last3=Yahi |first3=Nouara |last4=Barrantes |first4=Francisco J. |last5=Chahinian |first5=Henri |date=2018-05-22 |title=Anandamide Revisited: How Cholesterol and Ceramides Control Receptor-Dependent and Receptor-Independent Signal Transmission Pathways of a Lipid Neurotransmitter |journal=Biomolecules |volume=8 |issue=2 |pages=31 |doi=10.3390/biom8020031 |issn=2218-273X |pmc=6022874 |pmid=29789479|doi-access=free }}</ref>

==Uses and reactions==

Linoleic acid is a component of quick-[[drying oil]]s, which are useful in [[oil paint]]s and [[varnish]]es. These applications exploit the lability of the doubly [[allylic]] {{chem2|C\sH}} groups ({{chem2|\sCH\dCH\sC''H''2\sCH\dCH\s}}) toward oxygen in air ([[autoxidation]]). Addition of oxygen leads to [[Cross-link|crosslinking]] and formation of a stable film.<ref>{{Ullmann|author=Ulrich Poth|title=Drying Oils and Related Products|year=2002|doi=10.1002/14356007.a09_055}}</ref>

Reduction of the carboxylic acid group of linoleic acid yields [[linoleyl alcohol]].<ref>{{cite journal|first1=Homer|last1=Adkins|first2=R.H.|last2=Gillespie|doi=10.15227/orgsyn.029.0080|title=Oleyl Alcohol|journal=Organic Syntheses|year=1949|volume=29|page=80}}</ref>

Linoleic acid is a [[surfactant]] with a critical micelle concentration of 1.5 x 10⁻⁴ M @ pH 7.5.{{Cn|date=February 2021}}

Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. Research points to linoleic acid's anti-inflammatory, acne reductive, skin-lightening and moisture retentive properties when applied topically on the [[Human skin|skin]].<ref>{{cite journal

|last1=Diezel |first1=W.E.

|last2=Schulz |first2=E.

|last3=Skanks |first3=M.

|last4=Heise |first4=H.

| year=1993 |title=Plant oils: Topical application and anti-inflammatory effects (croton oil test) |journal=Dermatologische Monatsschrift |volume=179 |page=173}}</ref><ref>{{cite journal

|last1=Letawe |first1=C.

|last2=Boone |first2=M.

|last3=Pierard |first3=G.E.

|date=March 1998 |title=Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones |journal=Clinical and Experimental Dermatology |volume=23 |issue=2 |pages=56–58 |pmid=9692305 |doi=10.1046/j.1365-2230.1998.00315.x|s2cid=28594076}}</ref><ref>{{cite journal

|last1=Ando |first1=Hideya

|last2=Ryu |first2=Atsuko

|last3=Hashimoto |first3=Akira

|last4=Oka |first4=Masahiro

|last5=Ichihashi |first5=Masamitsu

|date=March 1998 |title=Linoleic acid and α-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin |journal=Archives of Dermatological Research |volume=290 |issue=7 |pages=375–381 |pmid=9749992 |doi=10.1007/s004030050320|s2cid=23036319}}</ref><ref>{{cite journal

|last1=Darmstadt |first1=Gary L.

|last2=Mao-Qiang |first2=M.

|last3=Chi |first3=E.

|last4=Saha |first4=S.K.

|last5=Ziboh |first5=V.A.

|last6=Black |first6=R.E.

|last7=Santosham |first7=M.

|last8=Elias |first8=P.M.

|year=2002 |title=Impact of topical oils on the skin barrier: possible implications for neonatal health in developing countries |journal=Acta Paediatrica |volume=91 |issue=5 |pages=546–554 |doi=10.1080/080352502753711678 |pmid=12113324 |citeseerx=10.1.1.475.1064}}</ref>

Linoleic acid is also used in some [[Soap|bar of soap]] products.

==Dietary sources==

{{See also|Vegetable oil#Composition of fats}}

It is abundant in [[safflower]], and [[corn oil|corn]] oil, and comprises over half their composition by weight. It is present in medium quantities in [[soybean oil]]s, [[sesame]], and [[almonds]].<ref name="USDA">{{cite web|year=2007 |work=USDA National Nutrient Database for Standard Reference, Release 20 |url=http://www.ars.usda.gov/ba/bhnrc/ndl |title=Nutrient Data Laboratory Home Page |publisher=U.S. Department of Agriculture, Agricultural Research Service |url-status=dead |archive-url=https://web.archive.org/web/20160414070404/http://www.ars.usda.gov/ba/bhnrc/ndl |archive-date=14 April 2016 }}</ref><ref>{{cite journal |last1=Kaur |first1=Narinder |last2=Chugh |first2=Vishal |last3=Gupta |first3=Anil K. |title=Essential fatty acids as functional components of foods- a review |journal=Journal of Food Science and Technology |date=October 2014 |volume=51 |issue=10 |pages=2289–2303 |doi=10.1007/s13197-012-0677-0 |pmid=25328170 |pmc=4190204 }}</ref>

{| class="wikitable sortable"

|-

!|Name||% LA^†||ref.

|-

|[[Salicornia oil]] ||75% ||

|-

|[[Safflower]] oil ||72-78% ||<ref name="Hall2015">{{cite book |last1=Hall III |first1=C. |editor1-last=Wrigley |editor1-first=Colin W. |editor2-last=Corke |editor2-first=Harold |editor3-last=Seetharaman |editor3-first=Koushik |editor4-last=Faubion |editor4-first=Jonathan |title=Encyclopedia of Food Grains |year=2015 |publisher=Academic Press |isbn=978-0-12-394786-4 |url=https://books.google.com/books?id=ce7tBgAAQBAJ&pg=PA255}}</ref>

|-

|[[Oenothera|Evening Primrose oil]] ||65-80% ||<ref>{{cite web |url=https://www.oilswelove.com/single-post/Evening-Primrose-Oil-for-Menopause-does-it-help |title=Evening Primrose Oil for Menopause does it help |date=2018-01-26 }}</ref>

|-

|[[Melon seed]] oil ||70% ||

|-

|[[Poppyseed oil]] ||70% ||

|-

|[[Grape seed oil]] ||69.6% ||

|-

|[[Opuntia ficus-indica|Prickly Pear]] seed oil ||63% ||

|-

|[[Artichoke oil]] ||60% ||

|-

|[[Hemp oil]] ||54.3% ||<ref>{{Cite journal|last1=Oomah|first1=B. Dave|last2=Busson|first2=Muriel|last3=Godfrey|first3=David V|last4=Drover|first4=John C. G|date=2002-01-01|title=Characteristics of hemp (Cannabis sativa L.) seed oil|journal=Food Chemistry|volume=76|issue=1|pages=33–43|doi=10.1016/S0308-8146(01)00245-X}}</ref>

|-

|[[Wheat germ oil]] ||55% ||

|-

|[[Cottonseed oil]] ||54% ||

|-

|[[Corn oil]] ||51.9% || <ref>{{cite web |title=FoodData Central |url=https://fdc.nal.usda.gov/fdc-app.html#/food-details/748323/nutrients |website=fdc.nal.usda.gov}}</ref>

|-

|[[Walnut oil]] ||51% ||

|-

|[[Soybean oil]] ||50.9% || <ref>{{cite web |title=FoodData Central |url=https://fdc.nal.usda.gov/fdc-app.html#/food-details/748366/nutrients |website=fdc.nal.usda.gov}}</ref>

|-

|[[Sesame oil]] ||45% ||

|-

|[[Pumpkin seed oil]] ||42-59% ||<ref>{{cite journal|author=Nawirska-Olszańska A, Kita A, Biesiada A, Sokół-Łętowska A, Kucharska AZ.|year=2013|title=Characteristics of antioxidant activity and composition of pumpkin seed oils in 12 cultivars|journal=Food Chemistry|volume=139|issue=1–4|pages=155–161|doi=10.1016/j.foodchem.2013.02.009|pmid=23561092}}</ref>

|-

|[[Rice bran oil]] ||39% ||

|-

|[[Argan oil]] ||37% ||

|-

|[[Pistachio oil]] ||32.7% ||

|-

|[[Peach]] oil ||29% ||<ref name=sdpk>{{cite journal |title=Essential oil extracted from peach (Prunus persica) kernel and its physicochemical and antioxidant properties | doi=10.1016/j.lwt.2011.05.012 | volume=44 |issue=10 |journal=LWT - Food Science and Technology |pages=2032–2039|year=2011 |last1=Wu |first1=Hao |last2=Shi |first2=John |last3=Xue |first3=Sophia |last4=Kakuda |first4=Yukio |last5=Wang |first5=Dongfeng |last6=Jiang |first6=Yueming |last7=Ye |first7=Xingqian |last8=Li |first8=Yanjun |last9=Subramanian |first9=Jayasankar }}</ref>

|-

|[[Almond]]s ||24% ||

|-

|[[Canola]] oil ||17.8% || <ref>{{cite web |title=FoodData Central |url=https://fdc.nal.usda.gov/fdc-app.html#/food-details/748278/nutrients |website=fdc.nal.usda.gov}}</ref>

|-

|[[Sunflower oil]] ||20.5% || <ref>{{cite web |title=FoodData Central |url=https://fdc.nal.usda.gov/fdc-app.html#/food-details/1750349/nutrients |website=fdc.nal.usda.gov}}</ref>

|-

|[[Chicken fat]] || 18-23% ||<ref>{{cite journal | title = The chemical composition of depot fats in chickens and turkeys | author = M. K. Nutter, E. E. Lockhart and R. S. Harris | year = 1943 | journal = Journal of the American Oil Chemists' Society | volume = 20 | issue = 11 | pages = 231–234 | doi = 10.1007/BF02630880| s2cid = 84893770 }}</ref>

|-

|[[Peanut oil]] ||19.6% || <ref>{{cite web |title=FoodData Central |url=https://fdc.nal.usda.gov/fdc-app.html#/food-details/1750348/nutrients |website=fdc.nal.usda.gov}}</ref>

|-

|Egg [[yolk]] ||16% ||

|-

|[[Linseed oil]] (flax), cold pressed||14.2% ||<ref>{{cite web |title=FoodData Central |url=https://fdc.nal.usda.gov/fdc-app.html#/food-details/167702/nutrients |website=fdc.nal.usda.gov}}</ref>

|-

|[[Lard]] ||10% ||

|-

|[[Palm oil]] ||10% ||

|-

|[[Olive oil]] ||8.4%||<ref>{{cite web |title=FoodData Central |url=https://fdc.nal.usda.gov/fdc-app.html#/food-details/748608/nutrients |website=fdc.nal.usda.gov}}</ref>

|-

|[[Cocoa butter]] ||3% ||

|-

|[[Macadamia oil]] ||2% ||

|-

|[[Butter]] ||2% ||

|-

|[[Coconut oil]] ||2% ||

|-

||&nbsp;

| colspan=2|<small>^†average val</small>

|}

===Other occurrences===

[[Cockroach]]es release oleic and linoleic acid upon death, which discourages other roaches from entering the area. This is similar to the mechanism found in ants and bees, which release oleic acid upon death.<ref name="BBC">{{cite news|url=http://news.bbc.co.uk/earth/hi/earth_news/newsid_8232000/8232607.stm|title=Earth News: Ancient 'smell of death' revealed|publisher=BBC|date=2009-09-09}}</ref>

==Health effects==

Consumption of linoleic acid has been associated with lowering the risk of [[cardiovascular disease]], diabetes and premature death.<ref>{{cite journal

|last1=Li |first1=Jun

|last2=Guasch-Ferré |first2=Marta

|last3=Li |first3=Yanping

|last4=Hu |first4=Frank B.

|year=2020|title=Dietary intake and biomarkers of linoleic acid and mortality: systematic review and meta-analysis of prospective cohort studies|journal=The American Journal of Clinical Nutrition|volume=112|issue=1|pages=150–167|pmid= 32020162|doi=10.1093/ajcn/nqz349|pmc=7326588}}</ref><ref>{{cite journal

|last1=Marangoni |first1=Franca

|last2=Agostoni |first2=Carlo

|last3=Borghi |first3=Claudio

|last4=Catapano |first4=Alberico L.

|last5=Cena |first5=Hellas

|last6=Ghiselli |first6=Andrea

|last7=La Vecchia |first7=Carlo

|last8=Lercker |first8=Giovanni

|last9=Manzato |first9=Enzo

|last10=Pirillo |first10=Angela

|last11=Riccardi |first11=Gabriele

|last12=Risé |first12=Patrizia

|last13=Visioli |first13=Francesco

|last14=Poli |first14=Andrea

|year=2020|title=Dietary linoleic acid and human health: Focus on cardiovascular and cardiometabolic effects|journal=Atherosclerosis|url=https://www.sciencedirect.com/science/article/abs/pii/S0021915019315758|volume=292|issue=|pages=90–98|doi=10.1016/j.atherosclerosis.2019.11.018|pmid=31785494|s2cid=208516015

}}</ref><ref>{{cite journal

|last1=Mousavi |first1=Seyed Mohammad

|last2=Jalilpiran |first2=Yahya

|last3=Karimi |first3=Elmira

|last4=Aune |first4=Dagfinn

|last5=Larijani |first5=Bagher

|last6=Mozaffarian |first6=Dariush

|last7=Willett |first7=Walter C.

|last8=Esmaillzadeh |first8=Ahmad

|year=2021|title=Dietary Intake of Linoleic Acid, Its Concentrations, and the Risk of Type 2 Diabetes: A Systematic Review and Dose-Response Meta-analysis of Prospective Cohort Studies|journal=Diabetes Care|volume=44|issue=9|pages=2173–2181|doi=10.2337/dc21-0438|pmid=34417277|s2cid=237255109

|doi-access=free}}</ref> There is high-quality evidence that increased intake of linoleic acid decreases total blood cholesterol and [[low-density lipoprotein]].<ref>[https://www.foodstandards.gov.au/consumer/labelling/nutrition/Documents/Systematic%20review%20fatty%20acids%20cholesterol.pdf "Systematic review of the evidence for relationships between saturated, cis monounsaturated, cis polyunsaturated fatty acids and selected individual fatty acids, and blood cholesterol concentration"]. foodstandards.gov.au. Retrieved 10 January 2023.</ref>

The [[American Heart Association]] advises people to replace saturated fat with linoleic acid to reduce CVD risk.<ref>{{Cite journal |vauthors=Sacks FM, Lichtenstein AH, Wu JH, Appel LJ, Creager MA, Kris-Etherton PM, Miller M, Rimm EB, Rudel LL, Robinson JG, Stone NJ, Van Horn LV |date=July 2017 |title=Dietary Fats and Cardiovascular Disease: A Presidential Advisory From the American Heart Association |journal=Circulation |volume=136 |issue=3 |pages=e1–e23 |doi=10.1161/CIR.0000000000000510 |pmid=28620111 |doi-access=free |s2cid=367602}}</ref>

==See also==

*[[Conjugated linoleic acid]]

*[[Essential fatty acid interactions]]

*[[Essential nutrient]]s

*[[Linolein]]

==References==

<references>

<ref name=sacc1844>F. Sacc (1844) "Ueber das Leinöl, seine physicalischen und chemischen Eigenscharften und seine Oxydationsproducte". ''Liebig Annalen'', volume 51, pages 213-230.</ref>

<ref name=sacc1845>F. Sacc (1845): "[https://books.google.com/books?id=pYk1AQAAMAAJ&pg=RA9-PA3&lpg=RA9-PA3 Expériences sur les propriétés physiques et chimiques de l'huile de Lin]". ''SChweizer. Gesell. N. Dekschr.'', volume 7</ref>

<ref name=burr1930>(1930: ''J Biol Chem'', volume 86, pages 587-</ref>

<ref name=raph1950>R. A. Raphael and Franz Sondheimer (1950): "The synthesis of long-chain aliphatic acids from acetylenic compounds. Part III. The synthesis of linoleic acid". ''Journal of the Chemical Society'' (''Resumed''), article 432, {{doi|10.1039/jr9500002100}}</ref>

</references>

==Further reading==

* {{cite web |title=Compound Summary: Linoleic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/linoleic_acid |website=PubChem |publisher=U.S. National Library of Medicine}}

==External links==

* [http://gmd.mpimp-golm.mpg.de/Spectrums/36c6cc53-c36d-4485-8c63-615d001552d3.aspx Linoleic acid MS Spectrum]

*[https://web.archive.org/web/20110827030232/http://lipidlibrary.aocs.org/Lipids/fa_poly/index.htm Fatty Acids: Methylene-Interrupted Double Bonds], AOCS Lipid Library

{{Fatty acids|state=expanded}}

{{Palm oil}}

{{Prostanoidergics}}

{{Leukotrienergics}}

{{Authority control}}

{{DEFAULTSORT:Linoleic Acid}}

[[Category:5α-Reductase inhibitors]]

[[Category:Alkenoic acids]]

[[Category:Aromatase inhibitors]]

[[Category:Essential fatty acids]]

[[Category:Essential nutrients]]

[[Category:Fatty acids]]

[[Category:Wood extractives]]