Linoleic acid

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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
ECHA InfoCard 100.000.428 Edit this at Wikidata
EC Number
  • 200-470-9
57557
KEGG
UNII
  • InChI=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- checkY
    Key: OYHQOLUKZRVURQ-HZJYTTRNSA-N checkY
  • 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-
    Key: OYHQOLUKZRVURQ-HZJYTTRNBX
  • CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
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]
Vapor pressure 16 Torr at 229 °C[citation needed]
Acidity (pKa) 4.77 at 25°C[4]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
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).
checkY verify (what is checkY☒N ?)

Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. 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 Latin 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: 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

Linoleic acid (LA: C
18H
32O
2; 18:2,n−6) is a precursor to arachidonic acid (AA: C
20H
32O
2; 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: C
22H
37NO
2; 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: C
22H
37NO
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 (C
20H
37NO
2; 18:2,n−6), an N-acylethanolamine,[clarification needed] - the ethanolamide of linoleic acid (LA: C
18H
32O
2; 18:2,n−6) and its metabolized incorporated ethanolamine (MEA: C
2H
7NO),[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−CH2−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 is a surfactant with a critical micelle concentration of 1.5 x 10−4 M @ pH 7.5.[citation needed]

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

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.[29][30]

Name % LA† ref.
Salicornia oil 75% [31]
Safflower oil 72–78% [32]
Evening Primrose oil 65–80% [33]
Melon seed oil 50–70% [34]
Poppyseed oil 74% [35]
Grape seed oil 70% [36]
Prickly Pear seed oil 50–78% [37]
Cardoon oil 60% [38][39]
Hemp oil 54.3% [40]
Wheat germ oil 56% [41][42]
Cottonseed oil 54% [43][44]
Corn oil 51.9% [45]
Walnut oil 50–72% [46][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%
Canola oil 17.8% [53]
Sunflower oil 20.5% [54]
Chicken fat 18–23% [55]
Peanut oil 19.6% [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 val, 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]

Health effects

Consumption of linoleic acid has been associated with lowering the risk of cardiovascular disease, diabetes and premature death.[60][61][62] There is high-quality evidence that increased intake of linoleic acid decreases total blood cholesterol and low-density lipoprotein.[63]

The American Heart Association advises people to replace saturated fat with linoleic acid to reduce CVD risk.[64]

See also

References

  1. ^ a b c The Merck Index, 11th Edition, 5382
  2. ^ a b c 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.
  3. ^ a b c d 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. Archived from the original on 28 October 2018. Retrieved 31 July 2017.
  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. PMC 2843518. 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. S2CID 9044197.
  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.
  11. ^ Burr GO, Burr MM (April 1930). "On the Nature and Rôle of the Fatty Acids Essential in Nutrition". J. Biol. Chem. 86 (2): 587–621. 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. ^ a b Whelan, Jay; Fritsche, Kevin (May 2013). "Linoleic Acid". Advances in Nutrition. 4 (3): 311–312. doi:10.3945/an.113.003772. PMC 3650500. 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 (15 February 2021). "Different Dietary N-3 Polyunsaturated Fatty Acid Formulations Distinctively Modify Tissue Fatty Acid and N-Acylethanolamine Profiles". Nutrients. 13 (2): 625. doi:10.3390/nu13020625. ISSN 2072-6643. PMC 7919039. PMID 33671938.
  17. ^ Salem, Norman; Van Dael, Peter (27 February 2020). "Arachidonic Acid in Human Milk". Nutrients. 12 (3): 626. doi:10.3390/nu12030626. ISSN 2072-6643. PMC 7146261. 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. (20 May 2017). "Linoleic Acid: A Nutritional Quandary". Healthcare. 5 (2): 25. doi:10.3390/healthcare5020025. ISSN 2227-9032. PMC 5492028. PMID 28531128.
  20. ^ PubChem. "Linoleoyl ethanolamide". pubchem.ncbi.nlm.nih.gov. Retrieved 29 October 2022.
  21. ^ Maccarrone, Mauro; Stelt, Marcelis van der; Rossi, Antonello; Veldink, Gerrit A.; Vliegenthart, Johannes F. G.; Agrò, Alessandro Finazzi (27 November 1998). "Anandamide Hydrolysis by Human Cells in Culture and Brain *". Journal of Biological Chemistry. 273 (48): 32332–32339. doi:10.1074/jbc.273.48.32332. hdl:1887/50863. ISSN 0021-9258. PMID 9822713.
  22. ^ Scala, Coralie Di; Fantini, Jacques; Yahi, Nouara; Barrantes, Francisco J.; Chahinian, Henri (22 May 2018). "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. PMC 6022874. PMID 29789479.
  23. ^ Ulrich Poth (2002). "Drying Oils and Related Products". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_055. ISBN 978-3527306732.
  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. S2CID 28594076.
  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. S2CID 23036319.
  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. CiteSeerX 10.1.1.475.1064. 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. Archived from the original on 14 April 2016.
  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. PMC 4190204. PMID 25328170.
  31. ^ Alfheeaid, Hani A.; et al. (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. PMC 9655280. PMID 36360016.
  32. ^ Hall III, C. (2015). Wrigley, Colin W.; Corke, Harold; Seetharaman, Koushik; Faubion, Jonathan (eds.). Encyclopedia of Food Grains. Academic Press. ISBN 978-0-12-394786-4.
  33. ^ "Evening Primrose Oil for Menopause does it help". 26 January 2018.
  34. ^ Zhang G, Li Z, Guo Z, Charalampopoulos D (June 2024). "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. doi:10.1016/j.jafr.2024.101182.
  35. ^ 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. Bibcode:2008BiTec..99.6354B. doi:10.1016/j.biortech.2007.12.009. PMID 18198133.
  36. ^ Martin ME, Grao-Cruces E, Millan-Linares MC, Montserrat-de la Paz S (October 2020). "Grape (Vitis vinifera L.) Seed Oil: A Functional Food from the Winemaking Industry". Foods. 9 (10): 1360. doi:10.3390/foods9101360. PMC 7599587. PMID 32992712.
  37. ^ Al-Naqeb G, Fiori L, Ciolli M, Aprea E (August 2021). "Prickly Pear Seed Oil Extraction, Chemical Characterization and Potential Health Benefits". Molecules. 26 (16): 5018. doi:10.3390/molecules26165018. PMC 8401162. PMID 34443606.
  38. ^ Varvouni EF, Graikou K, Gortzi O, Cheilari A, Aligiannis N, Chinou I (November 2021). "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. doi:10.3390/foods10112665. PMC 8618587. PMID 34828945.
  39. ^ Barbosa CH, Andrade MA, Vilarinho F, Castanheira I, Fernando AL, Loizzo MR, Sanches Silva A (May 2020). "A New Insight on Cardoon: Exploring New Uses besides Cheese Making with a View to Zero Waste". Foods. 9 (5): 564. doi:10.3390/foods9050564. hdl:10316/106089. PMC 7278730. PMID 32370268.
  40. ^ Oomah, B. Dave; Busson, Muriel; Godfrey, David V; Drover, John C. G. (1 January 2002). "Characteristics of hemp (Cannabis sativa L.) seed oil". Food Chemistry. 76 (1): 33–43. doi:10.1016/S0308-8146(01)00245-X.
  41. ^ Rahim MA, et al. (October 2023). "Essential Components from Plant Source Oils: A Review on Extraction, Detection, Identification, and Quantification". Molecules. 28 (19): 6881. doi:10.3390/molecules28196881. PMC 10574037. PMID 37836725.
  42. ^ Siraj, Naila (March 2022). "Wheat germ oil: a comprehensive review". Food Science and Technology. 42. doi:10.1590/fst.113721.
  43. ^ Lukonge E, Labuschagne MT, Hugo A (January 2007). "The evaluation of oil and fatty acid composition in seed of cotton accessions from various countries". J Sci Food Agric. 87 (2): 340–347. Bibcode:2007JSFA...87..340L. doi:10.1002/jsfa.2731. To download the article, click the title (not doi) and choose option [PDF] academia.edu.
  44. ^ Yang A, et al. (January 2021). "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. doi:10.3390/ani11010078. PMC 7824706. PMID 33406775.
  45. ^ "Oil, corn". FoodData Central. USDA. December 2019.
  46. ^ Masoodi L, et al. (September 2022). "An Overview on Traditional vs. Green Technology of Extraction Methods for Producing High Quality Walnut Oil". Agronomy. 12 (10): 2258. doi:10.3390/agronomy12102258.
  47. ^ "Oil, walnut". FoodData Central. USDA. April 2019. Retrieved 31 July 2024.
  48. ^ "Oil, soybean". FoodData Central. USDA. December 2019.
  49. ^ Dunford, Nurhan (August 2021). "Sesame Seed Oil Properties". OSU Extension. Retrieved 1 August 2024.
  50. ^ Oboulbiga EB, et al. (June 2023). "Physicochemical, potential nutritional, antioxidant and health properties of sesame seed oil: a review". Front. Nutr. 10. Table 2. doi:10.3389/fnut.2023.1127926. PMC 10292629. PMID 37377483.
  51. ^ Nawirska-Olszańska A, Kita A, Biesiada A, Sokół-Łętowska A, Kucharska AZ (2013). "Characteristics of antioxidant activity and composition of pumpkin seed oils in 12 cultivars". Food Chemistry. 139 (1–4): 155–161. 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; Subramanian, Jayasankar (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, canola". FoodData Central. USDA. December 2019.
  54. ^ "Oil, sunflower". FoodData Central. USDA. April 2021.
  55. ^ Nutter MK, Lockhart EE, Harris RS (1943). "The chemical composition of depot fats in chickens and turkeys". Journal of the American Oil Chemists' Society. 20 (11): 231–234. doi:10.1007/BF02630880. S2CID 84893770.
  56. ^ "Oil, peanut". FoodData Central. USDA. April 2021.
  57. ^ "Oil, flaxseed, cold pressed". FoodData Central. USDA. April 2019.
  58. ^ "Oil, olive, extra virgin". FoodData Central. USDA. December 2019.
  59. ^ "Earth News: Ancient 'smell of death' revealed". BBC. 9 September 2009.
  60. ^ 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. PMC 7326588. PMID 32020162.
  61. ^ Marangoni, Franca; Agostoni, Carlo; Borghi, Claudio; Catapano, Alberico L.; Cena, Hellas; Ghiselli, Andrea; La Vecchia, Carlo; Lercker, Giovanni; Manzato, Enzo; Pirillo, Angela; Riccardi, Gabriele; Risé, Patrizia; Visioli, Francesco; Poli, Andrea (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. S2CID 208516015.
  62. ^ 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. S2CID 237255109.
  63. ^ "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.
  64. ^ 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. doi:10.1161/CIR.0000000000000510. PMID 28620111. S2CID 367602.

Further reading

Retrieved from "https://mdwiki.org/wiki/Linoleic_acid"