Polyunsaturated fatty acid

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Polyunsaturated fatty acids (PUFAs) are fatty acids that contain more than one double bond in their backbone. This class includes many important compounds, such as essential fatty acids and those that give drying oils their characteristic property.

Polyunsaturated fatty acids can be classified in various groups by their chemical structure:

Based on the length of their carbon backbone, they are sometimes classified in two groups:[1]

  • short chain polyunsaturated fatty acids (SC-PUFA), with 18 carbon atoms
  • long-chain polyunsaturated fatty acids (LC-PUFA) with 20 or more carbon atoms

Dietary sources[edit]

Properties of vegetable oils[2][3]
Type Processing
treatment[4]
Saturated
fatty acids
Monounsaturated
fatty acids
Polyunsaturated
fatty acids
Smoke point
Total[2] Oleic
acid
(ω-9)
Total[2] α-Linolenic
acid
(ω-3)
Linoleic
acid
(ω-6)
ω-6:3
ratio
Avocado[5] 11.6 70.6 52–66[6] 13.5 1 12.5 12.5:1 250 °C (482 °F)[7]
Brazil nut[8] 24.8 32.7 31.3 42.0 0.1 41.9 419:1 208 °C (406 °F)[9]
Canola[10] 7.4 63.3 61.8 28.1 9.1 18.6 2:1 238 °C (460 °F)[9]
Coconut[11] 82.5 6.3 6 1.7 175 °C (347 °F)[9]
Corn[12] 12.9 27.6 27.3 54.7 1 58 58:1 232 °C (450 °F)[13]
Cottonseed[14] 25.9 17.8 19 51.9 1 54 54:1 216 °C (420 °F)[13]
Flaxseed/linseed[15] 9.0 18.4 18 67.8 53 13 0.2:1 107 °C (225 °F)
Grape seed   10.5 14.3 14.3   74.7 74.7 very high 216 °C (421 °F)[16]
Hemp seed[17] 7.0 9.0 9.0 82.0 22.0 54.0 2.5:1 166 °C (330 °F)[18]
Olive[19] 13.8 73.0 71.3 10.5 0.7 9.8 14:1 193 °C (380 °F)[9]
Palm[20] 49.3 37.0 40 9.3 0.2 9.1 45.5:1 235 °C (455 °F)
Peanut[21] 16.2 57.1 55.4 19.9 0.318 19.6 very high 232 °C (450 °F)[13]
Rice bran oil 25 38.4 2.2 34.4[22] 15.6 232 °C (450 °F)[23]
High-oleic safflower oil[24] 7.5 75.2 75.2 12.8 0 12.8 very high 212 °C (414 °F)[9]
Sesame[25] ? 14.2 39.7 39.3 41.7 0.3 41.3 138:1
Soybean[26] partially hydrogenated 14.9 43.0 42.5 37.6 2.6 34.9 13.4:1
Soybean[27] 15.6 22.8 22.6 57.7 7 51 7.3:1 238 °C (460 °F)[13]
Walnut oil[28] unrefined 9.1 22.8 22.2 63.3 10.4 52.9 5:1 160 °C (320 °F)[29]
Sunflower[30] 8.99 63.4 62.9 20.7 0.16 20.5 very high 227 °C (440 °F)[13]
Cottonseed[31] hydrogenated 93.6 1.5 0.6 0.2 0.3 1.5:1
Palm[32] hydrogenated 88.2 5.7 0
The nutritional values are expressed as percent (%) by mass of total fat.

Types[edit]

Methylene-interrupted polyenes[edit]

These fatty acids have 2 or more cis double bonds that are separated from each other by a single methylene bridge (-CH
2
-). This form is also sometimes called a divinylmethane pattern.[33]

Methylene- interrupted double bonds
−C−C=C−C−C=C−

The essential fatty acids are all omega-3 and -6 methylene-interrupted fatty acids. See more at Essential fatty acids—Nomenclature

Omega-3[edit]

Common name Lipid name Chemical name
Omega-3 fatty acids, polyunsaturated
Hexadecatrienoic acid (HTA) 16:3 (n-3) all-cis 7,10,13-hexadecatrienoic acid
Alpha-linolenic acid (ALA) 18:3 (n-3) all-cis-9,12,15-octadecatrienoic acid
Stearidonic acid (SDA) 18:4 (n-3) all-cis-6,9,12,15,-octadecatetraenoic acid
Eicosatrienoic acid (ETE) 20:3 (n-3) all-cis-11,14,17-eicosatrienoic acid
Eicosatetraenoic acid (ETA) 20:4 (n-3) all-cis-8,11,14,17-eicosatetraenoic acid
Eicosapentaenoic acid (EPA, Timnodonic acid) 20:5 (n-3) all-cis-5,8,11,14,17-eicosapentaenoic acid
Heneicosapentaenoic acid (HPA) 21:5 (n-3) all-cis-6,9,12,15,18-heneicosapentaenoic acid
Docosapentaenoic acid (DPA, Clupanodonic acid) 22:5 (n-3) all-cis-7,10,13,16,19-docosapentaenoic acid
Docosahexaenoic acid (DHA, Cervonic acid) 22:6 (n-3) all-cis-4,7,10,13,16,19-docosahexaenoic acid
Tetracosapentaenoic acid 24:5 (n-3) all-cis-9,12,15,18,21-tetracosapentaenoic acid
Tetracosahexaenoic acid (Nisinic acid) 24:6 (n-3) all-cis-6,9,12,15,18,21-tetracosahexaenoic acid

Omega-6[edit]

Common name Lipid name Chemical name
Omega-6 fatty acids, polyunsaturated
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
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) 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 (AdA) 22:4 (n-6) all-cis-7,10,13,16-docosatetraenoic acid
Docosapentaenoic acid (DPA) 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

Omega-9[edit]

Common name Lipid name Chemical name
Omega-9 fatty acids, mono- and polyunsaturated
Oleic acid 18:1 (n-9) cis-9-octadecenoic acid
Eicosenoic acid 20:1 (n-9) cis-11-eicosenoic acid
Mead acid 20:3 (n-9) all-cis-5,8,11-eicosatrienoic acid
Erucic acid 22:1 (n-9) cis-13-docosenoic acid
Nervonic acid 24:1 (n-9) cis-15-tetracosenoic acid
Monounsaturated

Conjugated fatty acids[edit]

Conjugated double bonds
-C=C-C=C-
Common name Lipid name Chemical name
Conjugated fatty acids  have two or more conjugated double bonds
Conjugated Linoleic Acids (two conjugated double bonds)
Rumenic acid 18:2 (n-7) 9Z,11E-octadeca-9,11-dienoic acid
  18:2 (n-6) 10E,12Z-octadeca-10,12-dienoic acid
Conjugated Linolenic Acids (three conjugated double bonds)
α-Calendic acid 18:3 (n-6) 8E,10E,12Z-octadecatrienoic acid
β-Calendic acid 18:3 (n-6) 8E,10E,12E-octadecatrienoic acid
Jacaric acid 18:3 (n-6) 8Z,10E,12Z-octadecatrienoic acid
α-Eleostearic acid 18:3 (n-5) 9Z,11E,13E-octadeca-9,11,13-trienoic acid
β-Eleostearic acid 18:3 (n-5) 9E,11E,13E-octadeca-9,11,13-trienoic acid
Catalpic acid 18:3 (n-5) 9Z,11Z,13E-octadeca-9,11,13-trienoic acid
Punicic acid 18:3 (n-5) 9Z,11E,13Z-octadeca-9,11,13-trienoic acid
Other
Rumelenic acid 18:3 (n-3) 9E,11Z,15E-octadeca-9,11,15-trienoic acid
α-Parinaric acid 18:4 (n-3) 9E,11Z,13Z,15E-octadeca-9,11,13,15-tetraenoic acid
β-Parinaric acid 18:4 (n-3) all trans-octadeca-9,11,13,15-tetraenoic acid
Bosseopentaenoic acid 20:5 (n-6) 5Z,8Z,10E,12E,14Z-eicosapentaenoic acid

Other polyunsaturated fatty acids[edit]

Common name Lipid name Chemical name
Pinolenic acid 18:3 (n-6) (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid
Sciadonic acid 20:3 (n-6) (5Z,11Z,14Z)-eicosa-5,11,14-trienoic acid

Function and effects[edit]

The biological effects of the ω-3 and ω-6 fatty acids are largely mediated by their mutual interactions, see Essential fatty acid interactions for detail.

Thermal degradation[edit]

Polyunsaturated fatty acids in culinary oils undergo oxidative deterioration at temperatures of 150 °C (302 °F). The heating causes a free radical chain reaction, which oxidizes the PUFAs into hydroperoxide, which further decomposes into a complex mixture of secondary products.[34]

See also[edit]

References[edit]

Citations[edit]

  1. ^ Buckley MT, et al. (2017). "Selection in Europeans on Fatty Acid Desaturases Associated with Dietary Changes". Mol Biol Evol. 34 (6): 1307–1318. doi:10.1093/molbev/msx103. PMC 5435082. PMID 28333262.
  2. ^ 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.
  3. ^ "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.
  4. ^ "USDA Specifications for Vegetable Oil Margarine Effective August 28, 1996" (PDF).
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  6. ^ Feramuz Ozdemir; Ayhan Topuz (May 2003). "Changes in dry matter, oil content and fatty acids composition of avocado during harvesting time and post-harvesting ripening period" (PDF). Elsevier. Retrieved 15 January 2020.
  7. ^ Marie Wong; Cecilia Requejo-Jackman; Allan Woolf (April 2010). "What is unrefined, extra virgin cold-pressed avocado oil?". Aocs.org. The American Oil Chemists’ Society. Retrieved 26 December 2019.
  8. ^ "Brazil nut oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  9. ^ a b c d e Katragadda, H. R.; Fullana, A. S.; Sidhu, S.; Carbonell-Barrachina, Á. A. (2010). "Emissions of volatile aldehydes from heated cooking oils". Food Chemistry. 120: 59–65. doi:10.1016/j.foodchem.2009.09.070.
  10. ^ "Canola oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  11. ^ "Coconut oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  12. ^ "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.
  13. ^ a b c d e Wolke, Robert L. (May 16, 2007). "Where There's Smoke, There's a Fryer". The Washington Post. Retrieved March 5, 2011.
  14. ^ "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.
  15. ^ "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.
  16. ^ 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.
  17. ^ Callaway J, Schwab U, Harvima I, Halonen P, Mykkänen O, Hyvönen P, Järvinen T (April 2005). "Efficacy of dietary hempseed oil in patients with atopic dermatitis". The Journal of Dermatological Treatment. 16 (2): 87–94. doi:10.1080/09546630510035832. PMID 16019622. S2CID 18445488.
  18. ^ "Smoke points of oils" (PDF).
  19. ^ "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.
  20. ^ "Palm oil, fat composition, 100 g". US National Nutrient Database, Release 28, United States Department of Agriculture. May 2016. Retrieved 6 September 2017.
  21. ^ "FoodData Central". fdc.nal.usda.gov.
  22. ^ Orthoefer, F. T. (2005). "Chapter 10: Rice Bran Oil". In Shahidi, F. (ed.). Bailey's Industrial Oil and Fat Products. Vol. 2 (6 ed.). John Wiley & Sons, Inc. p. 465. doi:10.1002/047167849X. ISBN 978-0-471-38552-3.
  23. ^ "Rice bran oil". RITO Partnership. Retrieved 22 January 2021.
  24. ^ "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.
  25. ^ "Oil, sesame, salad or cooking". FoodData Central. fdc.nal.usda.gov.
  26. ^ "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.
  27. ^ "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.
  28. ^ "Walnut oil, fat composition, 100 g". US National Nutrient Database, United States Department of Agriculture.
  29. ^ "Smoke Point of Oils". Baseline of Health. Jonbarron.org.
  30. ^ "FoodData Central". fdc.nal.usda.gov.
  31. ^ "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.
  32. ^ "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.
  33. ^ Baggott, James (1997). The divinylmethane pattern in fatty acids. Salt Lake City, UT: Knowledge Weavers.
  34. ^ Moya Moreno, MC; Mendoza Olivares, D; Amézquita López, FJ; Gimeno Adelantado, JV; Bosch Reig, F (September 13, 1999). "Analytical evaluation of polyunsaturated fatty acids degradation during thermal oxidation of edible oils by Fourier transform infrared spectroscopy". Talanta. 50 (2): 269–75. doi:10.1016/S0039-9140(99)00034-X. PMID 18967717.

General References[edit]