In biochemistry and nutrition, a polyunsaturated fat is a fat that contains a polyunsaturated fatty acid (abbreviated PUFA), which is a subclass of fatty acid characterized by a backbone with two or more carbon–carbon double bonds.[1][2] Some polyunsaturated fatty acids are essentials. Polyunsaturated fatty acids are precursors to and are derived from polyunsaturated fats, which include drying oils.[3]

Chemical structure of the polyunsaturated fatty acid linoleic acid.
3D representation of linoleic acid in a bent conformation.
Chemical structure of α-linolenic acid (ALA), an essential omega−3 fatty acid.

Nomenclature

The position of the carbon-carbon double bonds in carboxylic acid chains in fats is designated by Greek letters.[1] The carbon atom closest to the carboxyl group is the alpha carbon, the next carbon is the beta carbon and so on. In fatty acids the carbon atom of the methyl group at the end of the hydrocarbon chain is called the omega carbon because omega is the last letter of the Greek alphabet. Omega-3 fatty acids have a double bond three carbons away from the methyl carbon, whereas omega-6 fatty acids have a double bond six carbons away from the methyl carbon. The illustration below shows the omega-6 fatty acid, linoleic acid.

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:[4]

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

Production

PUFAs with 18 carbon atoms, which are the most common variety, are not produced by mammals. Since they have important dietary functions, their biosynthesis has received much attention. Plants produce PUFAs from oleic acid. Key enzymes are called fatty acid desaturases, which introduce additional double bonds. Desaturases convert oleic acid into linolenic acid the precursor to alpha-linoenic acid, gamma-linolenic acid, and eicosatrienoic acid.[5]

Industrial PUFAs are generally obtained by hydrolysis of fats that contain PUFAs. The process is complicated by the sensitive nature of PUFAs, leading to side reactions and colorization. Thus, steam hydrolysis often fails for this reason. Alkaline hydrolysis of fats followed by acidification is expensive. Lipases, a family of enzymes, show potential as mild and green catalysts for the production of PUFAs from triglycerides.[3]

In general, PUFAs are undesirable components of vegetable oils, so there is great interest in their removal from, say, olive oil. One technology for lowering the PUFA contact is by selective formation of derivatives with ureas.[3]

Reactions

From the perspective of analysis, PUFA's have high iodine numbers.

PUFAs are highly reactive compared to monounsaturated or saturated analogues. One practical consequence is that polyunsaturated fatty acids have poor shelf life, owing to their tendency toward autoxidation. Metals accelerate the degradation.

Hydrogenation of PUFAs gives less saturated derivatives. For unsaturated products from partial hydrogenation often contain some trans isomers. The trans monounsaturated C20 species elaidic acid can be prepared in this way.[3]

Peroxidation

Polyunsaturated fatty acids are susceptible to lipid peroxidation. The basis for this reactivity is the weakness of doubly allylic C-H bonds. They are drying oils.

Types

Methylene-interrupted polyenes

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.[6]

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 acidsNomenclature[7]

Omega-3

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

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

Conjugated fatty acids

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

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

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.

Health

Potential benefits

Because of their effects in the diet, unsaturated fats (monounsaturated and polyunsaturated) are often referred to as good fats; while saturated fats are sometimes referred to as bad fats. Some fat is needed in the diet, but it is usually considered that fats should not be consumed excessively, unsaturated fats should be preferred, and saturated fats in particular should be limited.[8][9][10][11]

In preliminary research, omega-3 fatty acids in algal oil, fish oil, fish and seafood have been shown to lower the risk of heart attacks.[12] Other preliminary research indicates that omega-6 fatty acids in sunflower oil and safflower oil may also reduce the risk of cardiovascular disease.[13]

Among omega-3 fatty acids, neither long-chain nor short-chain forms were consistently associated with breast cancer risk. High levels of docosahexaenoic acid (DHA), however, the most abundant omega-3 polyunsaturated fatty acid in erythrocyte (red blood cell) membranes, were associated with a reduced risk of breast cancer.[14] DHA is vital for the grey matter structure of the human brain, as well as retinal stimulation and neurotransmission.[1]

Contrary to conventional advice, an evaluation of evidence from 1966–1973 pertaining to the health impacts of replacing dietary saturated fat with linoleic acid found that participants in the group doing so had increased rates of death from all causes, coronary heart disease, and cardiovascular disease.[15] Although this evaluation was disputed by many scientists,[16] it fueled debate over worldwide dietary advice to substitute polyunsaturated fats for saturated fats.[17]

Taking isotope-reinforced polyunsaturated fatty acids, for example deuterated linoleic acid where two atoms of hydrogen substituted with its heavy isotope deuterium, with food (heavy isotope diet) can suppress lipid peroxidation and prevent or treat the associated diseases.[18][19]

Pregnancy

Polyunsaturated fat supplementation does not decrease the incidence of pregnancy-related disorders, such as hypertension or preeclampsia, but may increase the length of gestation slightly and decreased the incidence of early premature births.[1]

Expert panels in the United States and Europe recommend that pregnant and lactating women consume higher amounts of polyunsaturated fats than the general population to enhance the DHA status of the fetus and newborn.[1]

Cancer

Results from observational clinical trials on polyunsaturated fat intake and cancer have been inconsistent and vary by numerous factors of cancer incidence, including gender and genetic risk.[12] Some studies have shown associations between higher intakes and/or blood levels of polyunsaturated fat omega-3s and a decreased risk of certain cancers, including breast and colorectal cancer, while other studies found no associations with cancer risk.[12][20]

Dietary sources

Properties of vegetable oils[21][22]
The nutritional values are expressed as percent (%) by mass of total fat.
TypeProcessing
treatment[23]
Saturated
fatty acids
Monounsaturated
fatty acids
Polyunsaturated
fatty acids
Smoke point
Total[21]Oleic
acid
(ω-9)
Total[21]α-Linolenic
acid
(ω-3)
Linoleic
acid
(ω-6)
ω-6:3
ratio
Avocado[24]11.670.652–66
[25]
13.5112.512.5:1250 °C (482 °F)[26]
Brazil nut[27]24.832.731.342.00.141.9419:1208 °C (406 °F)[28]
Canola[29]7.463.361.828.19.118.62:1204 °C (400 °F)[30]
Coconut[31]82.56.361.7175 °C (347 °F)[28]
Corn[32]12.927.627.354.715858:1232 °C (450 °F)[30]
Cottonseed[33]25.917.81951.915454:1216 °C (420 °F)[30]
Cottonseed[34]hydrogenated93.61.50.60.20.31.5:1
Flaxseed/linseed[35]9.018.41867.853130.2:1107 °C (225 °F)
Grape seed 10.414.814.3  74.90.1574.7very high216 °C (421 °F)[36]
Hemp seed[37]7.09.09.082.022.054.02.5:1166 °C (330 °F)[38]
High-oleic safflower oil[39]7.575.275.212.8012.8very high212 °C (414 °F)[28]
Olive, Extra Virgin[40]13.873.071.310.50.79.814:1193 °C (380 °F)[28]
Palm[41]49.337.0409.30.29.145.5:1235 °C (455 °F)
Palm[42]hydrogenated88.25.70
Peanut[43]16.257.155.419.90.31819.661.6:1232 °C (450 °F)[30]
Rice bran oil2538.438.436.62.234.4[44]15.6:1232 °C (450 °F)[45]
Sesame[46]14.239.739.341.70.341.3138:1
Soybean[47]15.622.822.657.77517.3:1238 °C (460 °F)[30]
Soybean[48]partially hydrogenated14.943.042.537.62.634.913.4:1
Sunflower[49]8.9963.462.920.70.1620.5128:1227 °C (440 °F)[30]
Walnut oil[50]unrefined9.122.822.263.310.452.95:1160 °C (320 °F)[51]

Polyunsaturated fat can be found mostly in nuts, seeds, fish, seed oils, and oysters.[1] "Unsaturated" refers to the fact that the molecules contain less than the maximum amount of hydrogen (if there were no double bonds). These materials exist as cis or trans isomers depending on the geometry of the double bond.

FoodSaturatedMono-
unsaturated
Poly-
unsaturated
As weight percent (%) of total fat
Cooking oils
Algal oil[52]4924
Canola[53]86428
Coconut oil87130
Corn oil132459
Cottonseed oil[53]271954
Olive oil[54]147311
Palm kernel oil[53]86122
Palm oil[53]513910
Peanut oil[55]174632
Rice bran oil253837
Safflower oil, high oleic[56]67514
Safflower oil, linoleic[53][57]61475
Soybean oil152458
Sunflower oil[58]112069
Mustard oil115921
Dairy products
Butterfat[53]66304
Cheese, regular64293
Cheese, light60300
Ice cream, gourmet62294
Ice cream, light62294
Milk, whole62284
Milk, 2%62300
Whipping cream[59]*66265
Meats
Beef33385
Ground sirloin38444
Pork chop35448
Ham354916
Chicken breast293421
Chicken342330
Turkey breast302030
Turkey drumstick322230
Fish, orange roughy231546
Salmon283328
Hot dog, beef42485
Hot dog, turkey284022
Burger, fast food36446
Cheeseburger, fast food43407
Breaded chicken sandwich203932
Grilled chicken sandwich264220
Sausage, Polish374611
Sausage, turkey284022
Pizza, sausage413220
Pizza, cheese60285
Nuts
Almonds dry roasted96521
Cashews dry roasted205917
Macadamia dry roasted15792
Peanut dry roasted145031
Pecans dry roasted86225
Flaxseeds, ground82365
Sesame seeds143844
Soybeans142257
Sunflower seeds111966
Walnuts dry roasted92363
Sweets and baked goods
Candy, chocolate bar59333
Candy, fruit chews144438
Cookie, oatmeal raisin224727
Cookie, chocolate chip354218
Cake, yellow602510
Pastry, Danish503114
Fats added during cooking or at the table
Butter, stick63293
Butter, whipped62294
Margarine, stick183939
Margarine, tub163349
Margarine, light tub194633
Lard394511
Shortening254526
Chicken fat304521
Beef fat41433
Goose fat[60]335511
Dressing, blue cheese165425
Dressing, light Italian142458
Other
Egg yolk fat[61] 364416
Avocado[62] 167113
Unless else specified in boxes, then reference is:
* 3% is trans fats

Non-dietary applications

PUFA's are significant components of alkyd resins, which are used in coatings.[3]

See also

References

Citations

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General References

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