All Topics  
Omega-6 fatty acid

 

   Email Print
   Bookmark   Link






 

Omega-6 fatty acid



 
 
n-6 fatty acids (popularly referred to as ?-6 fatty acids or omega-6 fatty acids) are a family of unsaturated
Unsaturated fat

An unsaturated fat is a fat or fatty acid in which there are one or more double bonds in the fatty acid chain. A fat molecule is Monounsaturated fat if it contains one double bond, and polyunsaturated if it contains more than one double bond....
 fatty acid
Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail , which is either saturation or Unsaturated compound....
s which have in common a final carbon–carbon double bond in the
n-6
Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail , which is either saturation or Unsaturated compound....
 position; that is, the sixth bond from the end of the fatty acid.

The biological effects of the
n-6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body.






Discussion
Ask a question about 'Omega-6 fatty acid'
Start a new discussion about 'Omega-6 fatty acid'
Answer questions from other users
Full Discussion Forum



Encyclopedia


Lanumbering
n-6 fatty acids (popularly referred to as ?-6 fatty acids or omega-6 fatty acids) are a family of unsaturated
Unsaturated fat

An unsaturated fat is a fat or fatty acid in which there are one or more double bonds in the fatty acid chain. A fat molecule is Monounsaturated fat if it contains one double bond, and polyunsaturated if it contains more than one double bond....
 fatty acid
Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail , which is either saturation or Unsaturated compound....
s which have in common a final carbon–carbon double bond in the
n-6
Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail , which is either saturation or Unsaturated compound....
 position; that is, the sixth bond from the end of the fatty acid.

The biological effects of the
n-6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body. The conversion of tissue arachidonic acid (20:4n-6) to n-6 prostaglandin and n-6 leukotriene hormones provides many targets for pharmaceutical drug development and treatment to diminish excessive n-6 actions in atherosclerosis, asthma, arthritis, vascular disease, thrombosis, immune-inflammatory processes and tumor proliferation. Competitive interactions with the n-3 fatty acids
Omega-3 fatty acid

n-3 fatty acids are a family of unsaturated fat fatty acids that have in common a final carbon?carbon double bond#Bond order in the essential fatty acid#Nomenclature and terminology position; that is, the third bond from the methyl end of the fatty acid....
 affect the relative storage, mobilization, conversion and action of the n-3 and n-6 eicosanoid precursors. (See Essential fatty acid interactions
Essential fatty acid interactions

The actions of the Omega-3 fatty acid and Omega-6 fatty acid essential fatty acids are best characterized by their interactions; they cannot be understood separately....
 for more information.)

Key n-6 fatty acids

Linoleic acid
Linoleic acid

Linoleic acid is an unsaturated omega-6 fatty acid. It is a colorless liquid. In physiological literature, it is called 18:2. Chemically, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; the first double bond is located at the sixth carbon from the omega end....
 (18:2,
n-6), the shortest-chained n-6 fatty acid, is an essential fatty acid
Essential fatty acid

Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism from other components by any known chemical pathways, and therefore must be obtained from the diet....
. Arachidonic acid
Arachidonic acid

Arachidonic acid is an omega-6 fatty acid 20:4.It is the counterpart to the saturated arachidic acid found in peanut oil, ...
 (20:4) is a physiologically significant
n-6 fatty acid and is the precursor for prostaglandin
Prostaglandin

A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body....
s and other physiologically active molecules.

Negative health effects

Some medical research suggests that excessive levels of
n-6 fatty acids, relative to n-3 fatty acids, may increase the probability of a number of diseases and depression.

Modern Western diets typically have ratios of
n-6 to n-3 in excess of 10 to 1, some as high as 30 to 1. The optimal ratio is thought to be 4 to 1 or lower.

Excess
n-6 fats interfere with the health benefits of n-3 fats; in part because they compete for the same rate-limiting enzymes. A high proportion of n-6 to n-3 fat in the diet shifts the physiological state in the tissues toward the pathogenesis of many diseases: prothrombotic, proinflammatory and proconstrictive.

Chronic excessive production of
n-6 eicosanoids is associated with heart attacks, thrombotic stroke, arrhythmia, arthritis, osteoporosis, inflammation, mood disorders and cancer. Many of the medications used to treat and manage these conditions work by blocking the effects of the potent n-6 fat, arachidonic acid
Arachidonic acid

Arachidonic acid is an omega-6 fatty acid 20:4.It is the counterpart to the saturated arachidic acid found in peanut oil, ...
. Many steps in formation and action of n-6 hormones from n-6 arachidonic acid proceed more vigorously than the corresponding competitive steps in formation and action of n-3 hormones from n-3 eicosapentaenoic acid. The COX-1 and COX-2 inhibitor medications, used to treat inflammation and pain, work by preventing the COX
Cox

Cox may mean:* Coxswain* Cox Model Engines, made by L.M. Cox Manufacturing Inc. and later Cox Hobbies...
 enzymes from turning arachidonic acid into inflammatory compounds. (See Cyclooxygenase
Cyclooxygenase

Cyclooxygenase is an enzyme that is responsible for formation of important biological mediators called prostanoids . Pharmacological inhibition of COX can provide relief from the symptoms of inflammation and pain; this is the method of action of non-steroidal anti-inflammatory drugs, such as the well-known aspirin and ibuprofen....
 for more information.) The LOX inhibitor medications often used to treat asthma, work by preventing the LOX enzyme from converting arachidonic acid
Arachidonic acid

Arachidonic acid is an omega-6 fatty acid 20:4.It is the counterpart to the saturated arachidic acid found in peanut oil, ...
 into the leukotrienes. Many of the anti-mania medications used to treat bipolar disorder work by targeting the arachidonic acid
Arachidonic acid

Arachidonic acid is an omega-6 fatty acid 20:4.It is the counterpart to the saturated arachidic acid found in peanut oil, ...
 cascade in the brain.

A high consumption of
omega-6 polyunsaturated fatty acids (PUFAs), which are found in most types of vegetable oil, may increase the likelihood that postmenopausal women will develop breast cancer
Breast cancer

Breast cancer is a cancer that starts in the Cell of the breast in women and men. Worldwide, breast cancer is the second most common type of cancer after lung cancer and the fifth most common cause of cancer death....
. Similar effect was observed on prostate cancer
Prostate cancer

Prostate cancer is a disease in which cancer develops in the prostate, a gland in the male reproductive system. It occurs when cell s of the prostate Mutation and begin to multiply out of control....
. Other
analysis suggested an inverse association between total polyunsaturated fatty acids and breast cancer risk, but individual polyunsaturated fatty acids behaved differently [from each other]. [...] a 20:2 derivative of linoleic acid
Linoleic acid

Linoleic acid is an unsaturated omega-6 fatty acid. It is a colorless liquid. In physiological literature, it is called 18:2. Chemically, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; the first double bond is located at the sixth carbon from the omega end....
 [...] was inversely associated with the risk of breast cancer.

Dietary Linoleic Acid Requirement

Adding more controversy to the
n-6 fat issue is that the dietary requirement for linoleic acid (the key n-6 fatty acid), has been seriously questioned, because of a significant methodology error discovered by University of Toronto scientist, Stephen Cunnane. Cunnane discovered that the seminal research used to determine the dietary requirement for linoleic acid was based on feeding animals linoleic acid-deficient diets, which were simultaneously deficient in n-3 fats. The n-3 deficiency was not taken into account. The n-6 oils added back systematically to correct the deficiency also contained trace amounts of n-3 fats. Therefore the researchers were inadvertently correcting the n-3 deficiency as well. Ultimately, it took more oil to correct both deficiencies. According to Cunnane, this error overestimates LA requirements by 5 to 15 times.

Dietary sources

Oenothera Biennis 20050825 962
Four major food oils (palm, soybean, rapeseed and sunflower) provide more than 100 million metric tons annually, providing more than 32 million metric tons of n-6 linoleic acid and 4 million metric tons of n-3 alpha-linolenic acid
Dietary sources of
n-6 fatty acids

include:
  • poultry
    Poultry

    Poultry is the category of domesticated birds which some people keep for the purpose of collecting their egg , or kill for their meat and/or feathers....
  • egg
    Egg (food)

    An egg is a round or oval body laid by the female of many animals, consisting of an ovum surrounded by layers of membranes and an outer casing, which acts to nourish and protect a developing embryo and its nutrient reserves....
    s
  • cereal
    Cereal

    Cereals, or cereal grains, are mostly Poaceae cultivated for their edible brans or fruit seeds . Cereal grains are grown in greater quantities and provide more energy worldwide than any other type of crop; they are therefore staple foods....
    s
  • whole-grain breads
  • baked goods
  • nuts
    Nut (fruit)

    Nut is a general term for the large, dry, oily seed or fruit of some plant. While a wide variety of dried seeds and fruits are called nuts, only a certain number of them are considered by biologists to be true nuts....
  • most vegetable oils
  • evening primrose oil
    Oenothera

    Oenothera is a genus of about 125 species of Annual plant, Biennial plant and Perennial plant herbaceous flowering plants, native to the Americas....
  • borage oil
    Borage

    Borage , also known as "starflower" is an annual herb originating in Syria, but naturalized throughout the Mediterranean region, as well as Asia Minor, Europe, North Africa, and South America....
  • blackcurrant seed oil
    Blackcurrant

    The Blackcurrant is a species of Ribes berry native to central and northern Europe and northern Asia. It is also known as French "cassis".It is a small shrub growing to 1?2 m tall....
  • flax/linseed oil
    Linseed oil

    Linseed oil, also known as flax seed oil or simply flax oil, is a clear to yellowish drying oil derived from the dried ripe seeds of the flax plant ....
  • hemp oil
    Hemp oil

    Hempseed oil is pressed from the seed of the hemp plant . This oil typically contains between 30-35% oil by weight, and is extremely high in essential fatty acids....
  • soybean oil
  • cottonseed oil
    Cottonseed oil

    Cottonseed oil is a vegetable oil extracted from the seeds of the cotton plant after the cotton has been removed. It must be refined to remove gossypol, a naturally occurring toxin that protects the cotton plant from insect damage....
  • sunflower seed oil
  • corn oil
    Corn oil

    Corn oil is oil extracted from the cereal germ of corn . Its main use is in cooking, where its high smoke point makes refined corn oil a valuable frying oil....
  • safflower oil
  • pumpkin seeds
  • acai berry


List of n-6 fatty acids

Common name Lipid name Chemical name
Linoleic acid
Linoleic acid

Linoleic acid is an unsaturated omega-6 fatty acid. It is a colorless liquid. In physiological literature, it is called 18:2. Chemically, linoleic acid is a carboxylic acid with an 18-carbon chain and two cis double bonds; the first double bond is located at the sixth carbon from the omega end....
18:2 (n-6) 9,12-octadecadienoic acid
Gamma-linolenic acid
Gamma-Linolenic acid

?-Linolenic acid is an essential fatty acid found primarily in vegetable oils. It is sold as a dietary supplement for treating problems with inflammation and auto-immune diseases....
18:3 (n-6) 6,9,12-octadecatrienoic acid
Eicosadienoic acid 20:2 (n-6) 11,14-eicosadienoic acid
Dihomo-gamma-linolenic acid
Dihomo-gamma-linolenic acid

Dihomo-gamma-linolenic acid is a 20-carbon Omega-6 fatty acid. In physiological literature, it is given the name 20:3 . Chemically, DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end....
20:3 (n-6) 8,11,14-eicosatrienoic acid
Arachidonic acid
Arachidonic acid

Arachidonic acid is an omega-6 fatty acid 20:4.It is the counterpart to the saturated arachidic acid found in peanut oil, ...
20:4 (n-6) 5,8,11,14-eicosatetraenoic acid
Docosadienoic acid 22:2 (n-6) 13,16-docosadienoic acid
Adrenic acid
Docosatetraenoic acid

Docosatetraenoic acid designates any straight chain 22:4 fatty acid.One isomer is of particular interest* all-cis-7,10,13,16-docosatetraenoic acid is an omega-6_fatty acid with the trivial name adrenic acid....
22:4 (n-6) 7,10,13,16-docosatetraenoic acid
Docosapentaenoic acid
Docosapentaenoic acid

Docosapentaenoic acid designates any straight chain 22:5 fatty acid.Two isomers are of particular interest* all-cis-7,10,13,16,19-docosapentaenoic acid is an omega-3 fatty acid with the trivial name clupanodonic acid, commonly called DPA....
22:5 (n-6) 4,7,10,13,16-docosapentaenoic acid
Calendic acid
Calendic acid

Calendic acid is an Unsaturated fat, named for the Calendula , from which it is obtained. It is chemically similar to the conjugated linoleic acids; laboratory work suggests it may have similar health benefits....
18:3 (n-6) 8E,10E,12Z-octadecatrienoic acid


See also

  • Essential fatty acid interactions
    Essential fatty acid interactions

    The actions of the Omega-3 fatty acid and Omega-6 fatty acid essential fatty acids are best characterized by their interactions; they cannot be understood separately....
  • Essential nutrients
  • n-3 fatty acid
    Omega-3 fatty acid

    n-3 fatty acids are a family of unsaturated fat fatty acids that have in common a final carbon?carbon double bond#Bond order in the essential fatty acid#Nomenclature and terminology position; that is, the third bond from the methyl end of the fatty acid....
  • n-9 fatty acid
    Omega-9 fatty acid

    n-9 fatty acids are a family of unsaturated fat fatty acids which have in common a final carbon?carbon double bond#Bond order in the essential fatty acid#Nomenclature and terminology position; that is, the ninth bond from the end of the fatty acid....


Additional sources


Further reading


  • Erasmus, Udo. . 3rd ed. Burnaby (BC): Alive Books; 1993.