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{{short description|Polyunsaturated omega-6 fatty acid}}{{Distinguish|linolenic acid|alpha-linolenic acid|lipoic acid|linolelaidic acid}}{{Use dmy dates|date=August 2020}}{{chembox| Watchedfields = changed| 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 = (9Z,12Z)-Octadeca-9,12-dienoic acid!|Name||% LA†||ref.

cis,cis-9,12-Octadecadienoic acidC18:2 (Fatty acid#Nomenclature>Lipid numbers)| Section1 = {{Chembox Identifiers| IUPHAR_ligand = 1052

correct|chemspider}}| ChemSpiderID = 4444105

correct|FDA}}

correct|kegg}}| KEGG = C01595| Gmelin = 57557| Beilstein = 1727101| PubChem = 5280450| EC_number = 200-470-9| DrugBank = DB14104| 3DMet = B00328| UNII = 9KJL21T0QJ| InChI = 1/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-| InChIKey = OYHQOLUKZRVURQ-HZJYTTRNBX

correct|EBI}}| ChEMBL = 267476

correct|chemspider}}| StdInChI = 1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

correct|chemspider}}| StdInChIKey = OYHQOLUKZRVURQ-HZJYTTRNSA-N

correct|CAS}}| CASNo = 60-33-3

correct|EBI}}| ChEBI = 17351| SMILES = CCCCC/C=CC/C=CCCCCCCCC(=O)O }}| Section2 = {{Chembox Properties

H=32 | O=2| Appearance = Colorless oil| Density = 0.9 g/cm3The Merck Index, 11th Edition, 5382

-12

F}}{{convert

C

EDITION=97TH

PUBLISHER=CRC PRESS

ISBN=978-1-4987-5429-3

URL=HTTPS://BOOKS.GOOGLE.COM/BOOKS?ID=VVEZDAAAQBAJ, {{convert

C

ZVG=14230|CAS=60-33-3}}

229

F}} at 16 mmHg{{convert

C

230

F}} at 16 mmHg| Solubility = 0.139 mg/L

date=June 2011}}| pKa = 4.77 at 25°CNational Center for Biotechnology Information (2024). PubChem Compound Summary for CID 5280450, Linoleic Acid. Retrieved January 20, 2024 frompubchem.ncbi.nlm.nih.gov/compound/Linoleic-Acid. }}| Section3 = {hide}Chembox Hazards| NFPA-H = 2| NFPA-F = 1| NFPA-R = 0| MainHazards =

112

F{edih}| AutoignitionPt = }}| Section4 = | Section5 = | Section6 = }}Linoleic acid (LA) is an organic compound with the formula {{chem2|HOOC(CH2)7CHdCHCH2CHdCH(CH2)4CH3}}. Both alkene groups ({{chem2|sCHdCHs}}) are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.WEB,www.cyberlipid.org/fa/acid0001.htm, Fatty Acids, Cyber Lipid, 31 July 2017,www.cyberlipid.org/fa/acid0001.htm," title="web.archive.org/web/20181028011853www.cyberlipid.org/fa/acid0001.htm,">web.archive.org/web/20181028011853www.cyberlipid.org/fa/acid0001.htm, 28 October 2018, dead, Linoleic acid is a polyunsaturated, omega-6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents. It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.JOURNAL, 2843518, 19400700, 10.1146/annurev-nutr-080508-141108, 29, Is there a fatty acid taste?, 2009, Annual Review of Nutrition, 305–327, Mattes, Richard D., It is one of two essential fatty acids for humans, who must obtain it through their diet,JOURNAL, The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases, Simopoulos, Artemis P., Experimental Biology and Medicine, 2008, 233, 6 , 674–688, 10.3181/0711-mr-311, 18408140, 9044197, 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. In 1886, K. Peters determined the existence of two double bonds.(1886), Monatsch., volume 7, pages 522- Its essential role in human diet was discovered by G. O. Burr and others in 1930. 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. In physiology The consumption of linoleic acid is vital to proper health, as it is an essential fatty acid.JOURNAL, Whelan, Jay, Fritsche, Kevin, Linoleic Acid, Advances in Nutrition, May 2013, 4, 3, 311–312, 10.3945/an.113.003772, 3650500, 23674797, Metabolism and eicosanoids (File:Linoleic Acid Metabolism.gif){{clear-left}}Linoleic acid (LA: {{chem|C|18|H|32|O|2}}; 18:2, ω-6) is a precursor to arachidonic acid (AA: {{chem|C|20|H|32|O|2}}; 20:4, ω-6) with elongation and unsaturation.{{r|Whelan & Fritsche}} AA is the precursor to some prostaglandins,JOURNAL, 4723909, 25 August 1973, Wlodawer, Paulina, Samuelsson, Bengt, On the organization and mechanism of prostaglandin synthetase, The Journal of Biological Chemistry, 248, 16, 5673–5678, 10.1016/S0021-9258(19)43558-8, free, leukotrienes (LTA, LTB, LTC), thromboxane (TXA)JOURNAL, Terano, Takashi, Salmon, John A., Moncada, Salvador, February 1984, Biosynthesis and biological activity of leukotriene B5, Prostaglandins, 27, 2, 217–232, 10.1016/0090-6980(84)90075-3, 6326200, and the N-acylethanolamine (NAE) arachidonoylethanolamine (AEA: {{chem|C|22|H|37|NO|2}}; 20:4, ω-6),JOURNAL, Murru, Elisabetta, Lopes, Paula A., Carta, Gianfranca, Manca, Claudia, Abolghasemi, Armita, Guil-Guerrero, José L., Prates, José A. M., Banni, Sebastiano, 2021-02-15, Different Dietary N-3 Polyunsaturated Fatty Acid Formulations Distinctively Modify Tissue Fatty Acid and N-Acylethanolamine Profiles, Nutrients, en, 13, 2, 625, 10.3390/nu13020625, 33671938, 7919039, 2072-6643, free, and other endocannabinoids and eicosanoids.JOURNAL, Salem, Norman, Van Dael, Peter, 2020-02-27, Arachidonic Acid in Human Milk, Nutrients, en, 12, 3, 626, 10.3390/nu12030626, 32121018, 7146261, 2072-6643, free, The metabolism of LA to AA begins with the conversion of LA into gamma-linolenic acid (GLA), effected by Δ6-desaturase.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. JOURNAL, David F. Horrobin, 1993, Fatty acid metabolism in health and disease: the role of Δ-6-desaturase, American Journal of Clinical Nutrition, 57, 5 Suppl, 732S–737S, 10.1093/ajcn/57.5.732S, 8386433, free, GLA is converted to dihomo-γ-linolenic acid (DGLA), the immediate precursor to AA. LA is also converted by various lipoxygenases, cyclooxygenases, cytochrome P450 enzymes (the CYP monooxygenases), and non-enzymatic autoxidation mechanisms to mono-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 epoxygenases, 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.JOURNAL, Jandacek, Ronald J., 2017-05-20, Linoleic Acid: A Nutritional Quandary, Healthcare, 5, 2, 25, 10.3390/healthcare5020025, 2227-9032, 5492028, 28531128, free, Hydroperoxides derived from the metabolism of anandamide (AEA: {{chem|C|22|H|37|NO|2}}; 20:4,n-6), or its linoleoyl analogues, are by a lipoxygenase action found to be competitive inhibitors of brain and immune cell 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,{{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}}; 18:2, n-6) and its metabolized incorporated ethanolamine (MEA: {{chem|C|2|H|7|NO}}),WEB, PubChem, Linoleoyl ethanolamide,pubchem.ncbi.nlm.nih.gov/compound/5283446, 2022-10-29, pubchem.ncbi.nlm.nih.gov, en, is the first natural inhibitor of FAAH, discovered.JOURNAL, Maccarrone, Mauro, Stelt, Marcelis van der, Rossi, Antonello, Veldink, Gerrit A., Vliegenthart, Johannes F. G., Agrò, Alessandro Finazzi, 1998-11-27, Anandamide Hydrolysis by Human Cells in Culture and Brain *,www.jbc.org/article/S0021-9258(19)59084-6/abstract, Journal of Biological Chemistry, English, 273, 48, 32332–32339, 10.1074/jbc.273.48.32332, 0021-9258, 9822713, free, 1887/50863, free, JOURNAL, Scala, Coralie Di, Fantini, Jacques, Yahi, Nouara, Barrantes, Francisco J., Chahinian, Henri, 2018-05-22, Anandamide Revisited: How Cholesterol and Ceramides Control Receptor-Dependent and Receptor-Independent Signal Transmission Pathways of a Lipid Neurotransmitter, Biomolecules, 8, 2, 31, 10.3390/biom8020031, 2218-273X, 6022874, 29789479, free, Uses and reactions Linoleic acid is a component of quick-drying oils, which are useful in oil paints and varnishes. These applications exploit the lability of the doubly allylic {{chem2|CsH}} groups ({{chem2|sCHdCHsCH2sCHdCHs}}) toward oxygen in air (autoxidation). Addition of oxygen leads to crosslinking and formation of a stable film.{{Ullmann|author=Ulrich Poth|title=Drying Oils and Related Products|year=2002|doi=10.1002/14356007.a09_055}}Reduction of the carboxylic acid group of linoleic acid yields linoleyl alcohol.JOURNAL, Homer, Adkins, R.H., Gillespie, 10.15227/orgsyn.029.0080, Oleyl Alcohol, Organic Syntheses, 1949, 29, 80, 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 skin.DIEZEL >FIRST1=W.E.

FIRST2=E.

FIRST3=M.

FIRST4=H.

TITLE=PLANT OILS: TOPICAL APPLICATION AND ANTI-INFLAMMATORY EFFECTS (CROTON OIL TEST)

VOLUME=179, 173, LETAWE >FIRST1=C.

FIRST2=M.

FIRST3=G.E.

TITLE=DIGITAL IMAGE ANALYSIS OF THE EFFECT OF TOPICALLY APPLIED LINOLEIC ACID ON ACNE MICROCOMEDONES

VOLUME=23

PAGES=56–58

DOI=10.1046/J.1365-2230.1998.00315.X, 28594076, ANDO >FIRST1=HIDEYA

FIRST2=ATSUKO

FIRST3=AKIRA

FIRST4=MASAHIRO

FIRST5=MASAMITSU

TITLE=LINOLEIC ACID AND α-LINOLENIC ACID LIGHTENS ULTRAVIOLET-INDUCED HYPERPIGMENTATION OF THE SKIN

VOLUME=290

PAGES=375–381

DOI=10.1007/S004030050320, 23036319, DARMSTADT >FIRST1=GARY L.

FIRST2=M.

FIRST3=E.

FIRST4=S.K.

FIRST5=V.A.

FIRST6=R.E.

FIRST7=M.

FIRST8=P.M.

TITLE=IMPACT OF TOPICAL OILS ON THE SKIN BARRIER: POSSIBLE IMPLICATIONS FOR NEONATAL HEALTH IN DEVELOPING COUNTRIES

VOLUME=91

PAGES=546–554

PMID=12113324, 10.1.1.475.1064, Linoleic acid is also used in some bar of soap products. Dietary sources {{See also|Vegetable oil#Composition of fats}}It is abundant in safflower, and corn oil, and comprises over half their composition by weight. It is present in medium quantities in soybean oils, sesame, and almonds.WEB, 2007, USDA National Nutrient Database for Standard Reference, Release 20,www.ars.usda.gov/ba/bhnrc/ndl, Nutrient Data Laboratory Home Page, U.S. Department of Agriculture, Agricultural Research Service, dead,www.ars.usda.gov/ba/bhnrc/ndl," title="web.archive.org/web/20160414070404www.ars.usda.gov/ba/bhnrc/ndl,">web.archive.org/web/20160414070404www.ars.usda.gov/ba/bhnrc/ndl, 14 April 2016, JOURNAL, Kaur, Narinder, Chugh, Vishal, Gupta, Anil K., Essential fatty acids as functional components of foods- a review, Journal of Food Science and Technology, October 2014, 51, 10, 2289–2303, 10.1007/s13197-012-0677-0, 25328170, 4190204, {| class=“wikitable sortable”

Salicornia oil >

|

Safflower oil >

EDITOR1-LAST=WRIGLEY

EDITOR2-LAST=CORKE

EDITOR3-LAST=SEETHARAMAN

EDITOR4-LAST=FAUBION

TITLE=ENCYCLOPEDIA OF FOOD GRAINS

PUBLISHER=ACADEMIC PRESS

URL=HTTPS://BOOKS.GOOGLE.COM/BOOKS?ID=CE7TBGAAQBAJ&PG=PA255,

Oenothera>Evening Primrose oil

65-80%

HTTPS://WWW.OILSWELOVE.COM/SINGLE-POST/EVENING-PRIMROSE-OIL-FOR-MENOPAUSE-DOES-IT-HELP >TITLE=EVENING PRIMROSE OIL FOR MENOPAUSE DOES IT HELP, 2018-01-26,

Melon seed oil >

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Poppyseed oil >

|

Grape seed oil >

|

Opuntia ficus-indica>Prickly Pear seed oil

63%

Artichoke oil >

|

Hemp oil >

LAST2=BUSSON

LAST3=GODFREY

LAST4=DROVER

DATE=2002-01-01

JOURNAL=FOOD CHEMISTRY

ISSUE=1

DOI=10.1016/S0308-8146(01)00245-X,

Wheat germ oil >

|

Cottonseed oil >

|

Corn oil >

WEBSITE=FDC.NAL.USDA.GOV,

Walnut oil >

|

Soybean oil >

WEBSITE=FDC.NAL.USDA.GOV,

Sesame oil >

|

Pumpkin seed oil >

TITLE=CHARACTERISTICS OF ANTIOXIDANT ACTIVITY AND COMPOSITION OF PUMPKIN SEED OILS IN 12 CULTIVARS

VOLUME=139

PAGES=155–161

PMID=23561092,

Rice bran oil >

|

Argan oil >

|

Pistachio oil >

|

Peach oil >

VOLUME=44

JOURNAL=LWT - FOOD SCIENCE AND TECHNOLOGY

YEAR=2011

FIRST1=HAO

FIRST2=JOHN

FIRST3=SOPHIA

FIRST4=YUKIO

FIRST5=DONGFENG

FIRST6=YUEMING

FIRST7=XINGQIAN

FIRST8=YANJUN

FIRST9=JAYASANKAR,

Almonds >

|

Canola oil >

WEBSITE=FDC.NAL.USDA.GOV,

Sunflower oil >

WEBSITE=FDC.NAL.USDA.GOV,

Chicken fat >

YEAR = 1943

VOLUME = 20

PAGES = 231–234

S2CID = 84893770,

Peanut oil >

WEBSITE=FDC.NAL.USDA.GOV,

yolk >

|

Linseed oil (flax), cold pressed>

WEBSITE=FDC.NAL.USDA.GOV,

Lard >

|

Palm oil >

|

Olive oil >

WEBSITE=FDC.NAL.USDA.GOV,

Cocoa butter >

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Macadamia oil >

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Butter >

|

Coconut oil >

|

†average val

Other occurrences

Cockroaches 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.NEWS,news.bbc.co.uk/earth/hi/earth_news/newsid_8232000/8232607.stm, Earth News: Ancient ‘smell of death’ revealed, BBC, 2009-09-09,

Health effects

Consumption of linoleic acid has been associated with lowering the risk of cardiovascular disease, diabetes and premature death.LI >FIRST1=JUNFIRST2=MARTAFIRST3=YANPINGFIRST4=FRANK B.TITLE=DIETARY INTAKE AND BIOMARKERS OF LINOLEIC ACID AND MORTALITY: SYSTEMATIC REVIEW AND META-ANALYSIS OF PROSPECTIVE COHORT STUDIESVOLUME=112PAGES=150–167DOI=10.1093/AJCN/NQZ349, 7326588, MARANGONI >FIRST1=FRANCAFIRST2=CARLOFIRST3=CLAUDIOFIRST4=ALBERICO L.FIRST5=HELLASFIRST6=ANDREAFIRST7=CARLOFIRST8=GIOVANNIFIRST9=ENZOFIRST10=ANGELAFIRST11=GABRIELEFIRST12=PATRIZIAFIRST13=FRANCESCOFIRST14=ANDREATITLE=DIETARY LINOLEIC ACID AND HUMAN HEALTH: FOCUS ON CARDIOVASCULAR AND CARDIOMETABOLIC EFFECTSURL=HTTPS://WWW.SCIENCEDIRECT.COM/SCIENCE/ARTICLE/ABS/PII/S0021915019315758ISSUE=DOI=10.1016/J.ATHEROSCLEROSIS.2019.11.018S2CID=208516015, MOUSAVI >FIRST1=SEYED MOHAMMADFIRST2=YAHYAFIRST3=ELMIRAFIRST4=DAGFINNFIRST5=BAGHERFIRST6=DARIUSHFIRST7=WALTER C.FIRST8=AHMADTITLE=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 STUDIESVOLUME=44PAGES=2173–2181PMID=34417277, 237255109, free, There is high-quality evidence that increased intake of linoleic acid decreases total blood cholesterol and low-density lipoprotein.“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.The American Heart Association advises people to replace saturated fat with linoleic acid to reduce CVD risk.JOURNAL, 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, July 2017, Dietary Fats and Cardiovascular Disease: A Presidential Advisory From the American Heart Association, Circulation, 136, 3, e1–e23, 10.1161/CIR.0000000000000510, 28620111, free, 367602,

See also

• Conjugated linoleic acid
• Essential fatty acid interactions
• Essential nutrients
• Linolein

References

F. Sacc (1844) “Ueber das Leinöl, seine physicalischen und chemischen Eigenscharften und seine Oxydationsproducte”. Liebig Annalen, volume 51, pages 213-230.F. Sacc (1845): “Expériences sur les propriétés physiques et chimiques de l’huile de Lin”. SChweizer. Gesell. N. Dekschr., volume 7(1930: J Biol Chem, volume 86, pages 587-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}}

Further reading

• WEB, Compound Summary: Linoleic acid,pubchem.ncbi.nlm.nih.gov/compound/linoleic_acid, PubChem, U.S. National Library of Medicine,

External links

• Linoleic acid MS Spectrum
• lipidlibrary.aocs.org/Lipids/fa_poly/index.htm" title="web.archive.org/web/20110827030232lipidlibrary.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}}