Polyunsaturated fat
| Types offatsinfood |
|---|
| Components |
| Manufactured fats |
Inbiochemistryand nutrition, apolyunsaturated fatis afatthat contains apolyunsaturated fatty acid(abbreviatedPUFA), which is a subclass offatty acidcharacterized by a backbone with two or more carbon–carbondouble bonds.[1][2] Some polyunsaturated fatty acids areessentials.Polyunsaturated fatty acids are precursors to and are derived from polyunsaturatedfats,which includedrying oils.[3]
Nomenclature
[edit]The position of the carbon-carbon double bonds incarboxylic acidchains in fats is designated byGreek letters.[1]The carbon atom closest to thecarboxyl groupis thealphacarbon, the next carbon is thebetacarbon andso on.In fatty acids the carbon atom of themethyl groupat the end of the hydrocarbon chain is called theomegacarbon becauseomegais the last letter of the Greek alphabet.Omega-3 fatty acidshave a double bond three carbons away from the methyl carbon, whereasomega-6 fatty acidshave 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:
- methylene-interrupted polyenes
- conjugated fatty acids
- other PUFAs
Based on the length of their carbon backbone, they are sometimes classified in two groups:[4]All featurepentadienegroups.
- short chain polyunsaturated fatty acids (SC-PUFA),with 18 carbon atoms. These are more common. Key members includelinoleic acid,α-linolenic acid,andarachidonic acid.[5]
- long-chain polyunsaturated fatty acids (LC-PUFA)with 20 or more carbon atoms
Production
[edit]PUFAs with 18 carbon atoms, which are the most common variety, are not produced by mammals. Since they have important dietary functions, theirbiosynthesishas received much attention. Plants produce PUFAs fromoleic acid.Key enzymes are calledfatty acid desaturases,which introduce additional double bonds. Desaturases convert oleic acid intolinoleic acidthe precursor toalpha-linolenic acid,gamma-linolenic acidanddihomo-gamma-linolenic acid.[6]
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 andgreencatalysts for the production of PUFAs from triglycerides.[3]
In general, outside of dietary contexts, 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 withureas.[3]
Reactions
[edit]From the perspective of chemicalanalysis,PUFA's have highiodine numbers.These high values are simply a reflection of the fact that PUFAs arepolyunsaturated. Hydrogenation of PUFAs gives less saturated derivatives. For unsaturated products from partial hydrogenation often contain some trans isomers. The trans monounsaturated C20 specieselaidic acidcan be prepared in this way.[3]
Peroxidation
[edit]Polyunsaturated fatty acids are susceptible tolipid peroxidation,far moreso than monounsaturated or saturated analogues. The basis for this reactivity is the weakness of doublyallylicC-H bonds. They aredrying oils,i.e. film-forming liquids suitable as painting. One practical consequence is that polyunsaturated fatty acids have poor shelf life, owing to their tendency towardautoxidation,leading, in the case of edibles, torancidification.Metals accelerate the degradation. A range of reactions with oxygen occur. Products include fatty acidhydroperoxides,epoxy-hydroxy polyunsaturated fatty acids,jasmonates,divinylether fatty acids,andleaf aldehydes.Some of these derivatives are signallng molecules, some are used in plant defense (antifeedants), some are precursors to other metabolites that are used by the plant.[5]
Types
[edit]Methylene-interrupted polyenes
[edit]These fatty acids have 2 or morecisdouble bonds that are separated from each other by a singlemethylene bridge(-CH
2-). This form is also sometimes called adivinylmethane pattern.[7]
| −C−C=C−C−C=C− |
The essential fatty acids are all omega-3 and -6 methylene-interrupted fatty acids.See more atEssential fatty acids—Nomenclature[8]
Omega-3
[edit]| Common name | Lipid name | Chemical name |
|---|---|---|
| Hexadecatrienoic acid(HTA) | 16:3 (n-3) | all-cis-7,10,13-hexadecatrienoic acid |
| α-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 |
|---|---|---|
| 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
[edit]| -C=C-C=C- |
| Common name | Lipid name | Chemical name |
|---|---|---|
| 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, seeEssential fatty acid interactionsfor detail.
Health
[edit]Potential benefits
[edit]Because of their effects in the diet, unsaturated fats (monounsaturated and polyunsaturated) are often referred to asgood fats;while saturated fats are sometimes referred to asbad 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.[9][10][11][12]
In preliminary research,omega-3 fatty acidsin algal oil, fish oil, fish and seafood have been shown to lower the risk ofheart attacks.[13]Other preliminary research indicates thatomega-6 fatty acidsinsunflower oilandsafflower oilmay also reduce the risk of cardiovascular disease.[14]
Among omega-3 fatty acids, neither long-chain nor short-chain forms were consistently associated with breast cancer risk. High levels ofdocosahexaenoic 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.[15]DHAis vital for thegrey matter structure of the human brain,as well as retinal stimulation andneurotransmission.[1]
Contrary to conventional advice, an evaluation of evidence from 1966–1973 pertaining to the health impacts of replacing dietarysaturated fatwithlinoleic acidfound that participants in the group doing so hadincreasedrates of death from all causes, coronary heart disease, and cardiovascular disease.[16]Although this evaluation was disputed by many scientists,[17]it fueled debate over worldwide dietary advice to substitute polyunsaturated fats for saturated fats.[18]
Takingisotope-reinforcedpolyunsaturated fatty acids, for exampledeuterated linoleic acidwhere 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.[19][20]
Pregnancy
[edit]Polyunsaturated fat supplementation does not decrease the incidence of pregnancy-related disorders, such ashypertensionorpreeclampsia,but may increase the length ofgestationslightly 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
[edit]Results fromobservational clinical trialson polyunsaturated fat intake and cancer have been inconsistent and vary by numerous factors of cancer incidence, including gender and genetic risk.[13]Some studies have shown associations between higher intakes and/or blood levels of polyunsaturated fat omega-3s and a decreased risk of certain cancers, includingbreastandcolorectal cancer,while other studies found no associations with cancer risk.[13][21]
Dietary sources
[edit]| Type | Processing treatment[24] |
Saturated fatty acids |
Monounsaturated fatty acids |
Polyunsaturated fatty acids |
Smoke point | ||||
|---|---|---|---|---|---|---|---|---|---|
| Total[22] | Oleic acid (ω-9) |
Total[22] | α-Linolenic acid (ω-3) |
Linoleic acid (ω-6) |
ω-6:3 ratio | ||||
| Avocado[25] | 11.6 | 70.6 | 52–66 [26] |
13.5 | 1 | 12.5 | 12.5:1 | 250 °C (482 °F)[27] | |
| Brazil nut[28] | 24.8 | 32.7 | 31.3 | 42.0 | 0.1 | 41.9 | 419:1 | 208 °C (406 °F)[29] | |
| Canola[30] | 7.4 | 63.3 | 61.8 | 28.1 | 9.1 | 18.6 | 2:1 | 204 °C (400 °F)[31] | |
| Coconut[32] | 82.5 | 6.3 | 6 | 1.7 | 0.019 | 1.68 | 88:1 | 175 °C (347 °F)[29] | |
| Corn[33] | 12.9 | 27.6 | 27.3 | 54.7 | 1 | 58 | 58:1 | 232 °C (450 °F)[31] | |
| Cottonseed[34] | 25.9 | 17.8 | 19 | 51.9 | 1 | 54 | 54:1 | 216 °C (420 °F)[31] | |
| Cottonseed[35] | hydrogenated | 93.6 | 1.5 | 0.6 | 0.2 | 0.3 | 1.5:1 | ||
| Flaxseed/linseed[36] | 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)[37] | |
| Hemp seed[38] | 7.0 | 9.0 | 9.0 | 82.0 | 22.0 | 54.0 | 2.5:1 | 166 °C (330 °F)[39] | |
| High-oleic safflower oil[40] | 7.5 | 75.2 | 75.2 | 12.8 | 0 | 12.8 | very high | 212 °C (414 °F)[29] | |
| Olive,Extra Virgin[41] | 13.8 | 73.0 | 71.3 | 10.5 | 0.7 | 9.8 | 14:1 | 193 °C (380 °F)[29] | |
| Palm[42] | 49.3 | 37.0 | 40 | 9.3 | 0.2 | 9.1 | 45.5:1 | 235 °C (455 °F) | |
| Palm[43] | hydrogenated | 88.2 | 5.7 | 0 | |||||
| Peanut[44] | 16.2 | 57.1 | 55.4 | 19.9 | 0.318 | 19.6 | 61.6:1 | 232 °C (450 °F)[31] | |
| Rice bran oil | 25 | 38.4 | 38.4 | 36.6 | 2.2 | 34.4[45] | 15.6:1 | 232 °C (450 °F)[46] | |
| Sesame[47] | 14.2 | 39.7 | 39.3 | 41.7 | 0.3 | 41.3 | 138:1 | ||
| Soybean[48] | 15.6 | 22.8 | 22.6 | 57.7 | 7 | 51 | 7.3:1 | 238 °C (460 °F)[31] | |
| Soybean[49] | partially hydrogenated | 14.9 | 43.0 | 42.5 | 37.6 | 2.6 | 34.9 | 13.4:1 | |
| Sunflower[50] | 8.99 | 63.4 | 62.9 | 20.7 | 0.16 | 20.5 | 128:1 | 227 °C (440 °F)[31] | |
| Walnut oil[51] | unrefined | 9.1 | 22.8 | 22.2 | 63.3 | 10.4 | 52.9 | 5:1 | 160 °C (320 °F)[52] |
Polyunsaturated fat can be found mostly in nuts, seeds, fish, seed oils, andoysters.[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 ascisortransisomersdepending on the geometry of the double bond.
| Food | Saturated | Mono- unsaturated |
Poly- unsaturated |
|---|---|---|---|
| As weight percent (%) of total fat | |||
| Cooking oils | |||
| Algal oil[53] | 4 | 92 | 4 |
| Canola[54] | 8 | 64 | 28 |
| Coconut oil | 87 | 13 | 0 |
| Corn oil | 13 | 24 | 59 |
| Cottonseed oil[54] | 27 | 19 | 54 |
| Olive oil[55] | 14 | 73 | 11 |
| Palm kernel oil[54] | 86 | 12 | 2 |
| Palm oil[54] | 51 | 39 | 10 |
| Peanut oil[56] | 17 | 46 | 32 |
| Rice bran oil | 25 | 38 | 37 |
| Safflower oil, high oleic[57] | 6 | 75 | 14 |
| Safflower oil, linoleic[54][58] | 6 | 14 | 75 |
| Soybean oil | 15 | 24 | 58 |
| Sunflower oil[59] | 11 | 20 | 69 |
| Mustard oil | 11 | 59 | 21 |
| Dairy products | |||
| Butterfat[54] | 66 | 30 | 4 |
| Cheese,regular | 64 | 29 | 3 |
| Cheese, light | 60 | 30 | 0 |
| Ice cream, gourmet | 62 | 29 | 4 |
| Ice cream, light | 62 | 29 | 4 |
| Milk,whole | 62 | 28 | 4 |
| Milk, 2% | 62 | 30 | 0 |
| Whipping cream[60]* | 66 | 26 | 5 |
| Meats | |||
| Beef | 33 | 38 | 5 |
| Ground sirloin | 38 | 44 | 4 |
| Pork chop | 35 | 44 | 8 |
| Ham | 35 | 49 | 16 |
| Chicken breast | 29 | 34 | 21 |
| Chicken | 34 | 23 | 30 |
| Turkey breast | 30 | 20 | 30 |
| Turkey drumstick | 32 | 22 | 30 |
| Fish, orange roughy | 23 | 15 | 46 |
| Salmon | 28 | 33 | 28 |
| Hot dog, beef | 42 | 48 | 5 |
| Hot dog, turkey | 28 | 40 | 22 |
| Burger, fast food | 36 | 44 | 6 |
| Cheeseburger, fast food | 43 | 40 | 7 |
| Breaded chicken sandwich | 20 | 39 | 32 |
| Grilled chicken sandwich | 26 | 42 | 20 |
| Sausage, Polish | 37 | 46 | 11 |
| Sausage, turkey | 28 | 40 | 22 |
| Pizza, sausage | 41 | 32 | 20 |
| Pizza, cheese | 60 | 28 | 5 |
| Nuts | |||
| Almondsdry roasted | 9 | 65 | 21 |
| Cashewsdry roasted | 20 | 59 | 17 |
| Macadamiadry roasted | 15 | 79 | 2 |
| Peanutdry roasted | 14 | 50 | 31 |
| Pecansdry roasted | 8 | 62 | 25 |
| Flaxseeds,ground | 8 | 23 | 65 |
| Sesame seeds | 14 | 38 | 44 |
| Soybeans | 14 | 22 | 57 |
| Sunflower seeds | 11 | 19 | 66 |
| Walnutsdry roasted | 9 | 23 | 63 |
| Sweets and baked goods | |||
| Candy, chocolate bar | 59 | 33 | 3 |
| Candy, fruit chews | 14 | 44 | 38 |
| Cookie, oatmeal raisin | 22 | 47 | 27 |
| Cookie, chocolate chip | 35 | 42 | 18 |
| Cake, yellow | 60 | 25 | 10 |
| Pastry, Danish | 50 | 31 | 14 |
| Fats added during cooking or at the table | |||
| Butter,stick | 63 | 29 | 3 |
| Butter, whipped | 62 | 29 | 4 |
| Margarine,stick | 18 | 39 | 39 |
| Margarine, tub | 16 | 33 | 49 |
| Margarine, light tub | 19 | 46 | 33 |
| Lard | 39 | 45 | 11 |
| Shortening | 25 | 45 | 26 |
| Chicken fat | 30 | 45 | 21 |
| Beef fat | 41 | 43 | 3 |
| Goose fat[61] | 33 | 55 | 11 |
| Dressing, blue cheese | 16 | 54 | 25 |
| Dressing, light Italian | 14 | 24 | 58 |
| Other | |||
| Egg yolkfat[62] | 36 | 44 | 16 |
| Avocado[63] | 16 | 71 | 13 |
| Unless else specified in boxes, then reference is:[citation needed] | |||
| * 3% is trans fats | |||
Non-dietary applications
[edit]PUFA's are significant components ofalkyd resins,which are used incoatings.[3]
See also
[edit]References
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