Chemistry:Linoleic acid

From HandWiki
Short description: Polyunsaturated omega-6 fatty acid
Not to be confused with linolenic acid, alpha-linolenic acid, lipoic acid, or linolelaidic acid.
Linoleic acid
Names
Preferred IUPAC name
(9Z,12Z)-Octadeca-9,12-dienoic acid
Other names
cis,cis-9,12-Octadecadienoic acid
C18:2 (Lipid numbers)
Identifiers
3D model (JSmol)
3DMet
1727101
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 200-470-9
57557
KEGG
UNII
Properties
C18H32O2
Molar mass 280.452 g·mol−1
Appearance Colorless oil
Density 0.9 g/cm3[1]
Melting point −12 °C (10 °F)[1]
−6.9 °C (19.6 °F)[2]
−5 °C (23 °F)[3]
Boiling point 229 °C (444 °F) at 16 mmHg[2]
230 °C (446 °F) at 21 mbar[3]
230 °C (446 °F) at 16 mmHg[1]
0.139 mg/L[3]
Acidity (pKa) 4.77 at 25°C[4]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondFlammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 112 °C (234 °F)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Tracking categories (test):

Linoleic acid (LA) is an organic compound with the formula CH
3(CH
2)
4CH=CHCH
2CH=CH(CH
2)
7COOH. Both alkene groups (–CH=CH–) 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.[5]

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.[2] It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid.[6] It is one of two essential fatty acids for humans, who must obtain it through their diet,[7] and the most essential, because the body uses it as a base to make the others.

The word "linoleic" derives from la linum 'flax', and 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.[8][9] In 1886, K. Peters determined the existence of two double bonds.[10] Its essential role in human diet was discovered by G. O. Burr and others in 1930.[11] 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.[12]

In physiology

Main articles: Biology:Fatty acid desaturase and Fatty acid synthesis

The consumption of linoleic acid is vital to proper health, as it is an essential fatty acid.[13]

Metabolism and eicosanoids

File:Linoleic Acid Metabolism.gif

Linoleic acid (LA: C18H32O2; 18:2,n−6) is a precursor to arachidonic acid (AA: C20H32O2; 20:4,n−6) with elongation and unsaturation.[13] AA is the precursor to some prostaglandins,[14] leukotrienes (LTA, LTB, LTC), thromboxane (TXA)[15] and the N-acylethanolamine (NAE) arachidonoylethanolamine (AEA: C22H37NO2; 20:4,n−6),[16] and other endocannabinoids and eicosanoids.[17]

The metabolism of LA to AA begins with the conversion of LA into gamma-linolenic acid (GLA), effected by Δ6 desaturase.[18] 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.[19]

Hydroperoxides derived from the metabolism of anandamide (AEA: C22H37NO2; 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 (C20H37NO2; 18:2,n−6), an N-acylethanolamine,[clarification needed] - the ethanolamide of linoleic acid (LA: C18H32O2; 18:2,n−6) and its metabolized incorporated ethanolamine (MEA: C2H7NO),[20] is the first natural inhibitor of FAAH, discovered.[21][22]

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 C–H groups (–CH=CH–CH
2–CH=CH–) toward oxygen in air (autoxidation). Addition of oxygen leads to crosslinking and formation of a stable film.[23]

Reduction of the carboxylic acid group of linoleic acid yields linoleyl alcohol.[24]


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.[25][26][27][28]

Linoleic acid is also used in some bar of soap products.

Dietary sources

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.[29][30]

Name % LA† ref.
Salicornia oil 75% [31]
Poppyseed oil 74% [32]
Safflower oil 72–78% [33]
Grape seed oil 70% [34]
Evening Primrose oil 65–80% [35]
Cardoon oil 60% [36][37]
Wheat germ oil 56% [38][39]
Hemp oil 54.3% [40]
Cottonseed oil 54% [41][42]
Corn oil 51.9% [43]
Prickly Pear seed oil 50–78% [44]
Walnut oil 50–72% [45][46]
Melon seed oil 50–70% [47]
Soybean oil 50.9% [48]
Sesame oil 45% [49][50]
Pumpkin seed oil 42–59% [51]
Rice bran oil 39%
Argan oil 37%
Pistachio oil 32.7%
Peach oil 29% [52]
Almonds 24%
Sunflower oil 20.5% [53]
Peanut oil 19.6% [54]
Chicken fat 18–23% [55]
Canola oil 17.8% [56]
Egg yolk 16%
Linseed oil (flax), cold pressed 14.2% [57]
Lard 10%
Palm oil 10%
Olive oil 8.4% [58]
Tallow 3%
Cocoa butter 3%
Macadamia oil 2%
Butter 2%
Coconut oil 2%
  †average value, except the items where a range is given

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.[59]

While polyunsaturated fatty acids are unusual in plant cuticles, a diunsaturated dicarboxylic acid has been reported as a component of the surface waxes or polyesters of some plant species. Thus, octadeca-c6,c9-diene-1,18-dioate, a derivative of linoleic acid, is present in Arabidopsis and Brassica napus cuticle.[60] Taxoleic acid is isomeric to linoleic acid.

Health effects

Consumption of linoleic acid has been associated with lowering the risk of cardiovascular disease, diabetes and premature death.[61][62][63] There is high-quality evidence that increased intake of linoleic acid decreases total blood cholesterol and low-density lipoprotein.[64] Higher in vivo circulating and tissue levels of linoleic acid are associated with a lower risk of major cardiovascular events.[65] Clinical trials have shown that increased linoleic acid intake does not increase markers of inflammation or oxidative stress.[66][67]

The American Heart Association advises people to replace saturated fat with linoleic acid to reduce CVD risk.[68]

See also

References

  1. ↑ 1.0 1.1 1.2 The Merck Index, 11th Edition, 5382
  2. ↑ 2.0 2.1 2.2 William M. Haynes (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. pp. 3–338. ISBN 978-1-4987-5429-3. https://books.google.com/books?id=VVezDAAAQBAJ. 
  3. ↑ 3.0 3.1 3.2 3.3 Record of CAS RN 60-33-3 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ↑ 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.
  5. ↑ "Fatty Acids". Cyber Lipid. http://www.cyberlipid.org/fa/acid0001.htm. 
  6. ↑ Mattes, Richard D. (2009). "Is there a fatty acid taste?". Annual Review of Nutrition 29: 305–327. doi:10.1146/annurev-nutr-080508-141108. PMID 19400700. 
  7. ↑ Simopoulos, Artemis P. (2008). "The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases". Experimental Biology and Medicine 233 (6): 674–688. doi:10.3181/0711-mr-311. PMID 18408140. 
  8. ↑ F. Sacc (1844). "Ueber das Leinöl, seine physicalischen und chemischen Eigenschaften und seine Oxydationsproducte". Liebigs Annalen, volume 51, issue 2, pages 213–230. doi:10.1002/jlac.18440510207.
  9. ↑ F. Sacc (1845). "Expériences sur les propriétés physiques et chimiques de l'huile de Lin". Neue Denkschriften der Allg. Schweizerischen Gesellschaft für die Gesammten Naturwissenschaften, volume 7, pages 191–208 in pdf.
  10. ↑ Peters, Karl (December 1886). "Über Leinölsäure". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften 7: 552–555. doi:10.1007/BF01516597. https://archive.org/details/sim_monatshefte-fuer-chemie_1886_7_contents/page/554/mode/1up. 
  11. ↑ "On the Nature and Rôle of the Fatty Acids Essential in Nutrition". J. Biol. Chem. 86 (2): 587–621. April 1930. doi:10.1016/S0021-9258(20)78929-5. 
  12. ↑ Raphael, R.A.; Sondheimer, Franz (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, pp 2100–2103. doi:10.1039/jr9500002100. 
  13. ↑ 13.0 13.1 Whelan, Jay; Fritsche, Kevin (May 2013). "Linoleic Acid". Advances in Nutrition 4 (3): 311–312. doi:10.3945/an.113.003772. PMID 23674797. 
  14. ↑ Wlodawer, Paulina; Samuelsson, Bengt (25 August 1973). "On the organization and mechanism of prostaglandin synthetase". The Journal of Biological Chemistry 248 (16): 5673–5678. doi:10.1016/S0021-9258(19)43558-8. PMID 4723909. 
  15. ↑ Terano, Takashi; Salmon, John A.; Moncada, Salvador (February 1984). "Biosynthesis and biological activity of leukotriene B5". Prostaglandins 27 (2): 217–232. doi:10.1016/0090-6980(84)90075-3. PMID 6326200. 
  16. ↑ 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" (in en). Nutrients 13 (2): 625. doi:10.3390/nu13020625. ISSN 2072-6643. PMID 33671938. 
  17. ↑ Salem, Norman; Van Dael, Peter (2020-02-27). "Arachidonic Acid in Human Milk" (in en). Nutrients 12 (3): 626. doi:10.3390/nu12030626. ISSN 2072-6643. PMID 32121018. 
  18. ↑ 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. 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. doi:10.1093/ajcn/57.5.732S. PMID 8386433. 
  19. ↑ Jandacek, Ronald J. (2017-05-20). "Linoleic Acid: A Nutritional Quandary". Healthcare 5 (2): 25. doi:10.3390/healthcare5020025. ISSN 2227-9032. PMID 28531128. 
  20. ↑ PubChem. "Linoleoyl ethanolamide" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/5283446. 
  21. ↑ 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 *" (in English). Journal of Biological Chemistry 273 (48): 32332–32339. doi:10.1074/jbc.273.48.32332. ISSN 0021-9258. PMID 9822713. 
  22. ↑ 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. doi:10.3390/biom8020031. ISSN 2218-273X. PMID 29789479. 
  23. ↑ Ulrich Poth (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_055. 
  24. ↑ Adkins, Homer; Gillespie, R.H. (1949). "Oleyl Alcohol". Organic Syntheses 29: 80. doi:10.15227/orgsyn.029.0080. 
  25. ↑ Diezel, W.E.; Schulz, E.; Skanks, M.; Heise, H. (1993). "Plant oils: Topical application and anti-inflammatory effects (croton oil test)". Dermatologische Monatsschrift 179: 173. 
  26. ↑ Letawe, C.; Boone, M.; Pierard, G.E. (March 1998). "Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones". Clinical and Experimental Dermatology 23 (2): 56–58. doi:10.1046/j.1365-2230.1998.00315.x. PMID 9692305. 
  27. ↑ Ando, Hideya; Ryu, Atsuko; Hashimoto, Akira; Oka, Masahiro; Ichihashi, Masamitsu (March 1998). "Linoleic acid and α-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin". Archives of Dermatological Research 290 (7): 375–381. doi:10.1007/s004030050320. PMID 9749992. 
  28. ↑ Darmstadt, Gary L.; Mao-Qiang, M.; Chi, E.; Saha, S.K.; Ziboh, V.A.; Black, R.E.; Santosham, M.; Elias, P.M. (2002). "Impact of topical oils on the skin barrier: possible implications for neonatal health in developing countries". Acta Paediatrica 91 (5): 546–554. doi:10.1080/080352502753711678. PMID 12113324. 
  29. ↑ "Nutrient Data Laboratory Home Page". USDA National Nutrient Database for Standard Reference, Release 20. U.S. Department of Agriculture, Agricultural Research Service. 2007. https://www.ars.usda.gov/northeast-area/beltsville-md-bhnrc/beltsville-human-nutrition-research-center/methods-and-application-of-food-composition-laboratory/. 
  30. ↑ Kaur, Narinder; Chugh, Vishal; Gupta, Anil K. (October 2014). "Essential fatty acids as functional components of foods- a review". Journal of Food Science and Technology 51 (10): 2289–2303. doi:10.1007/s13197-012-0677-0. PMID 25328170. 
  31. ↑ Alfheeaid, Hani A. (November 2022). "Salicornia bigelovii, S. brachiata and S. herbacea: Their Nutritional Characteristics and an Evaluation of Their Potential as Salt Substitutes". Foods 11 (21): 3402. doi:10.3390/foods11213402. PMID 36360016. 
  32. ↑ Bozan, Berrin; Temelli, Feral (September 2008). "Chemical composition and oxidative stability of flax, safflower and poppy seed and seed oils". Bioresource Technology 99 (14): 6354–6359. doi:10.1016/j.biortech.2007.12.009. PMID 18198133. Bibcode: 2008BiTec..99.6354B. 
  33. ↑ Hall III, C. (2015). Wrigley, Colin W.; Corke, Harold; Seetharaman, Koushik et al.. eds. Encyclopedia of Food Grains. Academic Press. ISBN 978-0-12-394786-4. https://books.google.com/books?id=ce7tBgAAQBAJ&pg=PA255. 
  34. ↑ "Grape (Vitis vinifera L.) Seed Oil: A Functional Food from the Winemaking Industry". Foods 9 (10): 1360. October 2020. doi:10.3390/foods9101360. PMID 32992712. 
  35. ↑ "Evening Primrose Oil for Menopause does it help". 2018-01-26. https://www.oilswelove.com/single-post/Evening-Primrose-Oil-for-Menopause-does-it-help. 
  36. ↑ "Chemical and Biological Evaluation of the Oil and Seedcake from Seeds of a Greek Cardoon Cultivar as Potential Functional Vegetable Oil. Comparison with Sesame, Flaxseed and Extra Virgin Olive Oils". Foods 10 (11): 2665. November 2021. doi:10.3390/foods10112665. PMID 34828945. 
  37. ↑ "A New Insight on Cardoon: Exploring New Uses besides Cheese Making with a View to Zero Waste". Foods 9 (5): 564. May 2020. doi:10.3390/foods9050564. PMID 32370268. 
  38. ↑ "Essential Components from Plant Source Oils: A Review on Extraction, Detection, Identification, and Quantification". Molecules 28 (19): 6881. October 2023. doi:10.3390/molecules28196881. PMID 37836725. 
  39. ↑ Siraj, Naila (March 2022). "Wheat germ oil: a comprehensive review". Food Science and Technology 42. doi:10.1590/fst.113721. 
  40. ↑ Oomah, B. Dave; Busson, Muriel; Godfrey, David V; Drover, John C. G. (2002-01-01). "Characteristics of hemp (Cannabis sativa L.) seed oil". Food Chemistry 76 (1): 33–43. doi:10.1016/S0308-8146(01)00245-X. 
  41. ↑ "The evaluation of oil and fatty acid composition in seed of cotton accessions from various countries". J Sci Food Agric 87 (2): 340–347. January 2007. doi:10.1002/jsfa.2731. Bibcode: 2007JSFA...87..340L. https://scholar.google.com/scholar_lookup?&title=The%20evaluation%20of%20oil%20and%20fatty%20acid%20composition%20in%20seed%20of%20cotton%20accessions%20from%20various%20countries&journal=J%20Sci%20Food%20Agr&doi=10.1002%2Fjsfa.2731&volume=87&pages=340-347&publication_year=2007&author=Lukonge%2CE&author=Labuschagne%2CMT&author=Hugo%2CA#d=gs_qabs&t=1722117655066&u=%23p%3DMfUD-Yo-ZBoJ.  To download the article, click the title (not doi) and choose option [PDF] academia.edu.
  42. ↑ "Effects of Dietary Cottonseed Oil and Cottonseed Meal Supplementation on Liver Lipid Content, Fatty Acid Profile and Hepatic Function in Laying Hens". Animals 11 (1): 78. January 2021. doi:10.3390/ani11010078. PMID 33406775. 
  43. ↑ "Oil, corn". USDA. December 2019. https://fdc.nal.usda.gov/food-details/748323/nutrients. 
  44. ↑ "Prickly Pear Seed Oil Extraction, Chemical Characterization and Potential Health Benefits". Molecules 26 (16): 5018. August 2021. doi:10.3390/molecules26165018. PMID 34443606. 
  45. ↑ "An Overview on Traditional vs. Green Technology of Extraction Methods for Producing High Quality Walnut Oil". Agronomy 12 (10): 2258. September 2022. doi:10.3390/agronomy12102258. Bibcode: 2022Agron..12.2258M. 
  46. ↑ "Oil, walnut". USDA. April 2019. https://fdc.nal.usda.gov/food-details/171030/nutrients. 
  47. ↑ "Comparative extraction of melon seed (Cucumis melo L.) oil by conventional and enzymatic methods: Physicochemical properties and oxidative stability". Journal of Agriculture and Food Research 16. June 2024. doi:10.1016/j.jafr.2024.101182. 
  48. ↑ "Oil, soybean". USDA. December 2019. https://fdc.nal.usda.gov/food-details/748366/nutrients. 
  49. ↑ Dunford, Nurhan (August 2021). "Sesame Seed Oil Properties". https://extension.okstate.edu/fact-sheets/sesame-seed-oil-properties.html. 
  50. ↑ "Physicochemical, potential nutritional, antioxidant and health properties of sesame seed oil: a review". Front. Nutr. 10: Table 2. June 2023. doi:10.3389/fnut.2023.1127926. PMID 37377483. 
  51. ↑ "Characteristics of antioxidant activity and composition of pumpkin seed oils in 12 cultivars". Food Chemistry 139 (1–4): 155–161. 2013. doi:10.1016/j.foodchem.2013.02.009. PMID 23561092. 
  52. ↑ Wu, Hao; Shi, John; Xue, Sophia; Kakuda, Yukio; Wang, Dongfeng; Jiang, Yueming; Ye, Xingqian; Li, Yanjun et al. (2011). "Essential oil extracted from peach (Prunus persica) kernel and its physicochemical and antioxidant properties". LWT - Food Science and Technology 44 (10): 2032–2039. doi:10.1016/j.lwt.2011.05.012. 
  53. ↑ "Oil, sunflower". USDA. April 2021. https://fdc.nal.usda.gov/food-details/1750349/nutrients. 
  54. ↑ "Oil, peanut". USDA. April 2021. https://fdc.nal.usda.gov/food-details/1750348/nutrients. 
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  56. ↑ "Oil, canola". USDA. December 2019. https://fdc.nal.usda.gov/food-details/748278/nutrients. 
  57. ↑ "Oil, flaxseed, cold pressed". USDA. April 2019. https://fdc.nal.usda.gov/food-details/167702/nutrients. 
  58. ↑ "Oil, olive, extra virgin". USDA. December 2019. https://fdc.nal.usda.gov/food-details/748608/nutrients. 
  59. ↑ "Earth News: Ancient 'smell of death' revealed". BBC. 2009-09-09. http://news.bbc.co.uk/earth/hi/earth_news/newsid_8232000/8232607.stm. 
  60. ↑ Bonaventure, Gustavo; Ohlrogge, John; Pollard, Mike (2004). "Analysis of the aliphatic monomer composition of polyesters associated with Arabidopsis epidermis: occurrence of octadeca-cis-6, cis-9-diene-1,18-dioate as the major component". The Plant Journal 40 (6): 920–930. doi:10.1111/j.1365-313X.2004.02258.x. PMID 15584957. 
  61. ↑ Li, Jun; Guasch-Ferré, Marta; Li, Yanping; Hu, Frank B. (2020). "Dietary intake and biomarkers of linoleic acid and mortality: systematic review and meta-analysis of prospective cohort studies". The American Journal of Clinical Nutrition 112 (1): 150–167. doi:10.1093/ajcn/nqz349. PMID 32020162. 
  62. ↑ Marangoni, Franca; Agostoni, Carlo; Borghi, Claudio; Catapano, Alberico L.; Cena, Hellas; Ghiselli, Andrea; La Vecchia, Carlo; Lercker, Giovanni et al. (2020). "Dietary linoleic acid and human health: Focus on cardiovascular and cardiometabolic effects". Atherosclerosis 292: 90–98. doi:10.1016/j.atherosclerosis.2019.11.018. PMID 31785494. https://www.sciencedirect.com/science/article/abs/pii/S0021915019315758. 
  63. ↑ Mousavi, Seyed Mohammad; Jalilpiran, Yahya; Karimi, Elmira; Aune, Dagfinn; Larijani, Bagher; Mozaffarian, Dariush; Willett, Walter C.; Esmaillzadeh, Ahmad (2021). "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". Diabetes Care 44 (9): 2173–2181. doi:10.2337/dc21-0438. PMID 34417277. 
  64. ↑ "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.
  65. ↑ Marklund M, Wu JHY, Imamura F, Del Gobbo LC, Fretts A, de Goede J, Shi P, Tintle N, Wennberg M, Aslibekyan S, Chen TA, de Oliveira Otto MC, Hirakawa Y, Eriksen HH, Kröger J, Laguzzi F, Lankinen M, Murphy RA, Prem K, Samieri C, Virtanen J, Wood AC, Wong K, Yang WS, Zhou X, Baylin A, Boer JMA, Brouwer IA, Campos H, Chaves PHM, Chien KL, de Faire U, Djoussé L, Eiriksdottir G, El-Abbadi N, Forouhi NG, Michael Gaziano J, Geleijnse JM, Gigante B, Giles G, Guallar E, Gudnason V, Harris T, Harris WS, Helmer C, Hellenius ML, Hodge A, Hu FB, Jacques PF, Jansson JH, Kalsbeek A, Khaw KT, Koh WP, Laakso M, Leander K, Lin HJ, Lind L, Luben R, Luo J, McKnight B, Mursu J, Ninomiya T, Overvad K, Psaty BM, Rimm E, Schulze MB, Siscovick D, Skjelbo Nielsen M, Smith AV, Steffen BT, Steffen L, Sun Q, Sundström J, Tsai MY, Tunstall-Pedoe H, Uusitupa MIJ, van Dam RM, Veenstra J, Monique Verschuren WM, Wareham N, Willett W, Woodward M, Yuan JM, Micha R, Lemaitre RN, Mozaffarian D, Risérus U (2019). "Biomarkers of Dietary Omega-6 Fatty Acids and Incident Cardiovascular Disease and Mortality: An Individual-Level Pooled Analysis of 30 Cohort Studies". Circulation 139 (21): 2422–2436. doi:10.1161/CIRCULATIONAHA.118.038908. PMID 30971107. 
  66. ↑ Johnson GH, Fritsche K. (2012). "Effect of dietary linoleic acid on markers of inflammation in healthy persons: a systematic review of randomized controlled trials". Journal of the Academy of Nutrition and Dietetics 112 (7): 1029–1041. doi:10.1016/j.jand.2012.03.029. PMID 22889633. 
  67. ↑ Petersen KS, Maki KC, Calder PC, Belury MA, Messina M, Kirkpatrick CF, Harris WS. (2024). "Perspective on the health effects of unsaturated fatty acids and commonly consumed plant oils high in unsaturated fat". British Journal of Nutrition 30 (8): 1039–1050. doi:10.1017/S0007114524002459. PMID 39475012. 
  68. ↑ "Dietary Fats and Cardiovascular Disease: A Presidential Advisory From the American Heart Association". Circulation 136 (3): e1–e23. July 2017. doi:10.1161/CIR.0000000000000510. PMID 28620111. 

Further reading



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