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Omega-6 fatty acid

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For the 1920s French automobile, see Oméga-Six.
Not to be confused with Omega-3 fatty acid or Trans fatty acid.

Omega−6 fatty acids (also referred to as ω−6 fatty acids or n−6 fatty acids) are a family of polyunsaturated fatty acids that have in common a final carbon-carbon double bond in the n−6 position, that is, the sixth bond, counting from the methyl end.[1]

The evening primrose flower (O. biennis) produces an oil containing a high content of γ-linolenic acid, a type of omega−6 fatty acid.

Health effects

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The American Heart Association "supports an omega-6 PUFA intake of at least 5% to 10% of energy in the context of other AHA lifestyle and dietary recommendations. To reduce omega-6 PUFA intakes from their current levels would be more likely to increase than to decrease risk for coronary heart disease."[2]

A 2018 review found that an increased intake of omega−6 fatty acids reduces total serum cholesterol and may reduce myocardial infarction (heart attack), but found no significant change in LDL cholesterol and triglycerides.[3] A 2021 review found that omega−6 supplements do not affect the risk of CVD morbidity and mortality.[4]

A 2023 review found that omega−6 polyunsaturated fatty acids are associated with lower risk of high blood pressure.[5] Omega−6 fatty acids are not associated with atrial fibrillation.[6]

Dietary sources

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Dietary sources of omega−6 fatty acids include:[7]

Vegetable oils

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Vegetable oils are a major source of omega−6 linoleic acid. Worldwide, more than 100 million metric tons of vegetable oils are extracted annually from palm fruits, soybean seeds, grape seeds, and sunflower seeds, providing more than 32 million metric tons of omega−6 linoleic acid and 4 million metric tons of omega−3 alpha-linolenic acid.[8][9]

Properties of vegetable oils[10][11]
The nutritional values are expressed as percent (%) by mass of total fat.
Type Processing
treatment[12]		 Saturated
fatty acids		 Monounsaturated
fatty acids		 Polyunsaturated
fatty acids		 Smoke point
Total[10] Oleic
acid
(ω−9)		 Total[10] α-Linolenic
acid
(ω−3)		 Linoleic
acid
(ω−6)		 ω−6:3
ratio
Avocado[13] 11.6 70.6 52–66
[14]		 13.5 1 12.5 12.5:1 250 °C (482 °F)[15]
Brazil nut[16] 24.8 32.7 31.3 42.0 0.1 41.9 419:1 208 °C (406 °F)[17]
Canola[18] 7.4 63.3 61.8 28.1 9.1 18.6 2:1 204 °C (400 °F)[19]
Coconut[20] 82.5 6.3 6 1.7 0.019 1.68 88:1 175 °C (347 °F)[17]
Corn[21] 12.9 27.6 27.3 54.7 1 58 58:1 232 °C (450 °F)[19]
Cottonseed[22] 25.9 17.8 19 51.9 1 54 54:1 216 °C (420 °F)[19]
Cottonseed[23] hydrogenated 93.6 1.5 0.6 0.2 0.3 1.5:1
Flaxseed/linseed[24] 9.0 18.4 18 67.8 53 13 0.2:1 107 °C (225 °F)
Grape seed   10.4 14.8 14.3   74.9 0.15 74.7 very high 216 °C (421 °F)[25]
Hemp seed[26] 7.0 9.0 9.0 82.0 22.0 54.0 2.5:1 166 °C (330 °F)[27]
High-oleic safflower oil[28] 7.5 75.2 75.2 12.8 0 12.8 very high 212 °C (414 °F)[17]
Olive (extra virgin)[29] 13.8 73.0 71.3 10.5 0.7 9.8 14:1 193 °C (380 °F)[17]
Palm[30] 49.3 37.0 40 9.3 0.2 9.1 45.5:1 235 °C (455 °F)
Palm[31] hydrogenated 88.2 5.7 0
Peanut[32] 16.2 57.1 55.4 19.9 0.318 19.6 61.6:1 232 °C (450 °F)[19]
Rice bran oil 25 38.4 38.4 36.6 2.2 34.4[33] 15.6:1 232 °C (450 °F)[34]
Sesame[35] 14.2 39.7 39.3 41.7 0.3 41.3 138:1
Soybean[36] 15.6 22.8 22.6 57.7 7 51 7.3:1 238 °C (460 °F)[19]
Soybean[37] partially hydrogenated 14.9 43.0 42.5 37.6 2.6 34.9 13.4:1
Sunflower[38] 8.99 63.4 62.9 20.7 0.16 20.5 128:1 227 °C (440 °F)[19]
Walnut oil[39] unrefined 9.1 22.8 22.2 63.3 10.4 52.9 5:1 160 °C (320 °F)[40]
 
Comparison of dietary fat composition from a 1995 study.

List of omega−6 fatty acids

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The chemical structure of linoleic acid, a common omega−6 fatty acid found in many nuts, seeds, and vegetable oils.
Common name Lipid name Chemical name
Linoleic acid (LA) 18:2 (n−6) all-cis-9,12-octadecadienoic acid
Gamma-linolenic acid (GLA) 18:3 (n−6) all-cis-6,9,12-octadecatrienoic acid
Calendic acid 18:3 (n−6) 8E,10E,12Z-octadecatrienoic acid
Eicosadienoic acid 20:2 (n−6) all-cis-11,14-eicosadienoic acid
Dihomo-gamma-linolenic acid (DGLA) 20:3 (n−6) all-cis-8,11,14-eicosatrienoic acid
Arachidonic acid (AA, ARA) 20:4 (n−6) all-cis-5,8,11,14-eicosatetraenoic acid
Docosadienoic acid 22:2 (n−6) all-cis-13,16-docosadienoic acid
Adrenic acid 22:4 (n−6) all-cis-7,10,13,16-docosatetraenoic acid
Osbond acid 22:5 (n−6) all-cis-4,7,10,13,16-docosapentaenoic acid
Tetracosatetraenoic acid 24:4 (n−6) all-cis-9,12,15,18-tetracosatetraenoic acid
Tetracosapentaenoic acid 24:5 (n−6) all-cis-6,9,12,15,18-tetracosapentaenoic acid

The melting point of the fatty acids increases as the number of carbons in the chain increases.[41]

See also

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References

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  1. ^ Chow, Ching Kuang (2001). Fatty Acids in Foods and Their Health Implications. New York: Routledge Publishing. OCLC 25508943.[page needed]
  2. ^ Harris, WS; Mozaffarian, D; Rimm, E; Kris-Etherton, P; Rudel, LL; Appel, LJ; Engler, MM; Engler, MB; Sacks, F (2009). "Omega-6 fatty acids and risk for cardiovascular disease: a science advisory from the American Heart Association Nutrition Subcommittee of the Council on Nutrition, Physical Activity, and Metabolism; Council on Cardiovascular Nursing; and Council on Epidemiology and Prevention". Circulation. 119 (6): 902–7. doi:10.1161/CIRCULATIONAHA.108.191627. PMID 19171857.
  3. ^ Hooper L, Al-Khudairy L, Abdelhamid AS, Rees K, Brainard JS, Brown TJ, Ajabnoor SM, O'Brien AT, Winstanley LE, Donaldson DH, Song F, Deane KH (2018). "Omega-6 fats for the primary and secondary prevention of cardiovascular disease". Cochrane Database of Systematic Reviews. 2018 (11). CD011094. doi:10.1002/14651858.CD011094.pub4. PMC 6516799. PMID 30488422.
  4. ^ Mazidi M, Shekoohi N, Katsiki N, Banach M (2021). "Omega-6 fatty acids and the risk of cardiovascular disease: insights from a systematic review and meta-analysis of randomized controlled trials and a Mendelian randomization study". Archives of Medical Science. 18 (2): 466–479. doi:10.5114/aoms/136070. PMC 8924827. PMID 35316920.
  5. ^ Hajihashemi P, Feizi A, Heidari Z, Haghighatdoost F. (2023). "Association of omega-6 polyunsaturated fatty acids with blood pressure: A systematic review and meta-analysis of observational studies". Critical Reviews in Food Science and Nutrition. 63 (14): 2247–2259. doi:10.1080/10408398.2021.1973364. PMID 36939291.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ Garg PK, Guan W, Nomura S, Weir NL, Tintle N, Virtanen JK, Hirakawa Y, Qian F, Sun Q, Rimm E, Lemaitre RN, Jensen PN, Heckbert SR, Imamura F, Steur M, Leander K, Laguzzi F, Voortman T, Ninomiya T, Mozaffarian D, Harris WS, Siscovick DS, Tsai MY (2023). "Fatty Acids and Outcomes Research Consortium (FORCE). n-6 fatty acid biomarkers and incident atrial fibrillation: an individual participant-level pooled analysis of 11 international prospective studies". The American Journal of Clinical Nutrition. 118 (5): 921–929. doi:10.1016/j.ajcnut.2023.09.008. PMID 37769813.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ "Food sources of total omega 6 fatty acids". Archived from the original on 2011-10-07. Retrieved 2011-09-04.
  8. ^ Gunstone, Frank (December 2007). "Market update: Palm oil". International News on Fats, Oils and Related Materials. 18 (12): 835–36. Archived from the original on 2013-04-03.
  9. ^ "Soybean Oil Prices Suddenly Diverge from Energy Market" (PDF). Oilseeds: World Market and Trade (January 2009). USDA. 2009-01-12. FOP 1-09. Archived from the original (PDF) on 2013-03-09. Retrieved 2019-08-09., Table 03: Major Vegetable Oils: World Supply and Distribution at Oilseeds: World Markets and Trade Monthly Circular Archived 2010-10-18 at the Wayback Machine
  10. ^ a b c "US National Nutrient Database, Release 28". United States Department of Agriculture. May 2016. All values in this table are from this database unless otherwise cited or when italicized as the simple arithmetic sum of other component columns.
  11. ^ "Fats and fatty acids contents per 100 g (click for "more details"). Example: Avocado oil (user can search for other oils)". Nutritiondata.com, Conde Nast for the USDA National Nutrient Database, Standard Release 21. 2014. Retrieved 7 September 2017. Values from Nutritiondata.com (SR 21) may need to be reconciled with most recent release from the USDA SR 28 as of Sept 2017.
  12. ^ "USDA Specifications for Vegetable Oil Margarine Effective August 28, 1996" (PDF).
  13. ^ "Avocado oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  14. ^ Ozdemir, Feramuz; Topuz, Ayhan (June 2004). "Changes in dry matter, oil content and fatty acids composition of avocado during harvesting time and post-harvesting ripening period". Food Chemistry. 86 (1): 79–83. doi:10.1016/j.foodchem.2003.08.012.
  15. ^ Wong M, Requejo-Jackman C, Woolf A (April 2010). "What is unrefined, extra virgin cold-pressed avocado oil?". Aocs.org. The American Oil Chemists' Society. Retrieved 26 December 2019.
  16. ^ "Brazil nut oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  17. ^ a b c d Katragadda, Harinageswara Rao; Fullana, Andrés; Sidhu, Sukh; Carbonell-Barrachina, Ángel A. (May 2010). "Emissions of volatile aldehydes from heated cooking oils". Food Chemistry. 120 (1): 59–65. doi:10.1016/j.foodchem.2009.09.070.
  18. ^ "Canola oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  19. ^ a b c d e f Wolke RL (May 16, 2007). "Where There's Smoke, There's a Fryer". The Washington Post. Retrieved March 5, 2011.
  20. ^ "Coconut oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  21. ^ "Corn oil, industrial and retail, all purpose salad or cooking, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  22. ^ "Cottonseed oil, salad or cooking, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  23. ^ "Cottonseed oil, industrial, fully hydrogenated, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  24. ^ "Linseed/Flaxseed oil, cold pressed, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  25. ^ Garavaglia J, Markoski MM, Oliveira A, Marcadenti A (2016). "Grape Seed Oil Compounds: Biological and Chemical Actions for Health". Nutrition and Metabolic Insights. 9: 59–64. doi:10.4137/NMI.S32910. PMC 4988453. PMID 27559299.
  26. ^ Callaway, James; Schwab, Ursula; Harvima, Ilkka; Halonen, Pirjo; Mykkänen, Otto; Hyvönen, Pekka; Järvinen, Tomi (April 2005). "Efficacy of dietary hempseed oil in patients with atopic dermatitis". Journal of Dermatological Treatment. 16 (2): 87–94. doi:10.1080/09546630510035832. PMID 16019622.
  27. ^ Melina V. "Smoke points of oils" (PDF). veghealth.com. The Vegetarian Health Institute.
  28. ^ "Safflower oil, salad or cooking, high oleic, primary commerce, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  29. ^ "Olive oil, salad or cooking, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  30. ^ "Palm oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  31. ^ "Palm oil, industrial, fully hydrogenated, filling fat, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  32. ^ "Oil, peanut". FoodData Central. usda.gov.
  33. ^ Orthoefer, Frank T. (2020). "Rice Bran Oil". Bailey's Industrial Oil and Fat Products. pp. 1–25. doi:10.1002/047167849X.bio015.pub2. ISBN 978-0-471-38460-1.
  34. ^ "Rice bran oil". RITO Partnership. Retrieved 22 January 2021.
  35. ^ "Oil, sesame, salad or cooking". FoodData Central. fdc.nal.usda.gov. 1 April 2019.
  36. ^ "Soybean oil, salad or cooking, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  37. ^ "Soybean oil, salad or cooking, (partially hydrogenated), fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  38. ^ "FoodData Central". fdc.nal.usda.gov.
  39. ^ "Walnut oil, fat composition, 100 g". US National Nutrient Database, United States Department of Agriculture.
  40. ^ "Smoke Point of Oils". Baseline of Health. Jonbarron.org.
  41. ^ "Biochemical Properties of Lipids". The Medical Biochemistry Page. 2020-04-30. Retrieved 2022-05-11.

Bibliography

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