All Topics  
Essential fatty acid

 

   Email Print
   Bookmark   Link






 

Essential fatty acid



 
 
Essential fatty acids, or EFAs, are 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 that cannot be constructed within an organism (generally all references are to humans) from other components by any known chemical pathways, and therefore must be obtained from the diet. The term refers to fatty acids involved in biological processes, and not those which may just play a role as fuel. As many of the compounds created from essential fatty acids can be taken directly in the diet, it is possible that the amounts required in the diet (if any) are overestimated.






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



Encyclopedia


Essential fatty acids, or EFAs, are 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 that cannot be constructed within an organism (generally all references are to humans) from other components by any known chemical pathways, and therefore must be obtained from the diet. The term refers to fatty acids involved in biological processes, and not those which may just play a role as fuel. As many of the compounds created from essential fatty acids can be taken directly in the diet, it is possible that the amounts required in the diet (if any) are overestimated. It is also possible they can be underestimated as organisms can still survive in non-ideal, malnourished conditions.

There are two families of EFAs: ?-3 (or omega-3
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....
 or n-3) and ?-6 (omega-6
Omega-6 fatty acid

n-6 fatty acids are a family of unsaturated fat fatty acids which have in common a final carbon?carbon double bond#Bond order in the Fatty acid#Nomenclature position; that is, the sixth bond from the end of the fatty acid....
, n-6). Fats from each of these families are essential, as the body can convert one omega-3 to another omega-3, for example, but cannot create an omega-3 from omega-6 or saturated fats. They were originally designated as Vitamin F when they were discovered as essential nutrients in 1923. In 1930, work by Burr, Burr and Miller showed that they are better classified with the fat
Fat

Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. Chemistry, fats are generally ester of glycerol and fatty acids....
s than with the vitamin
Vitamin

A vitamin is an organic compound required as a nutrient in tiny amounts by an organism. A compound is called a vitamin when it cannot be biosynthesis in sufficient quantities by an organism, and must be obtained from the diet....
s.

Functions

The biological effects of the ?-3 and ?-6 fatty acids are mediated by their mutual interactions, 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 detail.
In the body, essential fatty acids serve multiple functions. In each of these, the balance between dietary ?-3 and ?-6 strongly affects function.
  • They are modified to make
    • the classic eicosanoid
      Eicosanoid

      In biochemistry, eicosanoids are lipid signaling made by oxygenation of twenty-carbon essential fatty acids, .They exert complex control over many bodily systems, mainly in inflammation or Immune system, and as messengers in the central nervous system....
      s (affecting inflammation
      Inflammation

      Inflammation is the complex biological response of Blood vessel tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. It is a protective attempt by the organism to remove the injurious stimuli as well as initiate the healing process for the tissue....
       and many other cellular functions)
    • the endocannabinoids (affecting mood, behavior and inflammation)
    • the lipoxin
      Lipoxin

      Lipoxins are a series of Inflammation mediators. Lipoxins are short lived endogenously produced nonclassic eicosanoids whose appearance in inflammation signals the resolution of inflammation....
      s from ?-6 EFAs and resolvins
      Resolvins

      Resolvins are compounds that are made by the human body from the Omega-3 fatty acid eicosapentaenoic acid and docosahexaenoic acid . They are produced by the Cyclooxygenase pathway especially in the presence of aspirin....
       from ?-3 (in the presence of aspirin, downregulating inflammation.)
    • the isofuran
      Isofuran

      Isofurans are nonclassic eicosanoids formed nonenzymatically by free radical mediated peroxidation of arachidonic acid. The isofurans are similar to the isoprostanes and are formed under similar conditions, but contain a substituted tetrahydrofuran ring....
      s, neurofuran
      Neurofuran

      Neurofurans are 22-carbon compounds formed nonenzymatically by free radical mediated peroxidation of Docosahexaenoic_acid , an Omega-3_fatty_acid Essential_fatty_acid....
      s, isoprostane
      Isoprostane

      The isoprostanes are prostaglandin-like compounds formed in vivo from the free radical-catalyzed Lipid peroxidationof essential fatty acids without the direct action of cyclooxygenase enzyme....
      s, hepoxilin
      Hepoxilin

      Hepoxilins are nonclassic eicosanoid hormones involved in inflammation....
      s, epoxyeicosatrienoic acid
      Epoxyeicosatrienoic acid

      The Epoxyeicosatrienoic acids or EETs are signaling molecules formed by the action of Cytochrome P450 oxidase on 20-carbon essential fatty acids, such as arachidonic acid, from which it is produced by the enzyme epoxygenase....
      s (EETs) and Neuroprotectin D
      Neuroprotectin

      Neuroprotectin D1 is a docosanoid derived from the polyunsaturated fatty acid docosahexaenoic acid , which is a component of fish oil and the most important omega-3 PUFA....
  • They form lipid raft
    Lipid raft

    A lipid raft is a cholesterol-enriched microdomain in cell membranes....
    s (affecting cellular signaling)
  • They act on DNA (activating or inhibiting transcription factors such as NF?B, which is linked to pro-inflammatory cytokine
    Cytokine

    Cytokines are a category of signaling molecules that, like hormones and neurotransmitters, are used extensively in cell communication. They are proteins, peptides or glycoproteins....
     production)


Fatty acids are straight chain hydrocarbons possessing a carboxyl
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 (COOH) group at one end. The carbon next to the carboxylate is known as a, the next carbon ß, and so forth. Since biological fatty acids can be of different lengths, the last position is labelled as a "?", the last letter in the Greek alphabet
Greek alphabet

The Greek alphabet is a set of twenty-four letters that has been used to write the Greek language since the late 9th century BC or early 8th century BCE....
. Since the physiological properties of unsaturated fatty acids largely depend on the position of the first unsaturation relative to the end position and not the carboxylate, the position is signified by (? minus n). For example, the term ?-3 signifies that the first double bond exists as the third carbon-carbon bond from the terminal CH3 end of the carbon chain. The number of carbons and the number of double bonds is also listed. ?-3 18:4 (stearidonic acid
Stearidonic acid

Stearidonic acid is an Omega-3 fatty acid essential fatty acid, sometimes called moroctic acid. It is biosynthesized from alpha-linolenic acid by the enzyme desaturase....
) or 18:4 ?-3 or 18:4 n-3 indicates an 18-carbon chain with 4 double bonds, and with the first double bond in the third position from the CH3 end. Double bonds are cis
Geometric isomerism

In chemistry, cis-trans isomerism or geometric isomerism or configuration isomerism or E-Z isomerism is a form of stereoisomerism describing the orientation of functional groups within a molecule....
 and separated by a single methylene (CH2) group unless otherwise noted. So in free fatty acid form, the chemical structure of stearidonic acid is:

Examples

For complete tables of ?-3 and ?-6 essential fatty acids, see Polyunsaturated fatty acid
Polyunsaturated fatty acid

Polyunsaturated fatty acids are those which contain more than one double bond....
s.
The essential fatty acids start with the short chain polyunsaturated fatty acids (SC-PUFA):
  • ?-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....
    s:
    • a-Linolenic acid
      Alpha-linolenic acid

      a-Linolenic acid is an organic compound found in many common Vegetable fats and oils. IUPAC nomenclature of organic chemistry, it is named all-cis-9,12,15-octadecatrienoic acid....
       or ALA (18:3)
  • ?-6 fatty acids
    Omega-6 fatty acid

    n-6 fatty acids are a family of unsaturated fat fatty acids which have in common a final carbon?carbon double bond#Bond order in the Fatty acid#Nomenclature position; that is, the sixth bond from the end of the fatty acid....
    :
    • 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....
       or LA (18:2)
These two fatty acids cannot be synthesised
Biosynthesis

Biosynthesis is a phenomenon wherein chemical compounds are produced from simpler reagents. Biosynthesis, unlike chemosynthesis, takes place within living organisms and is generally catalyst by enzymes....
 by humans, as humans lack the desaturase
Desaturase

A Desaturase is an enzyme which removes two hydrogen atoms from an organic compound, creating a carbon/carbon Covalent bond. Desaturases are classified as...
 enzymes required for their production.

They form the starting point for the creation of longer and more desaturated fatty acids, which are also referred to as long-chain polyunsaturated fatty acids (LC-PUFA):
  • ?-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....
    s:
    • eicosapentaenoic acid
      Eicosapentaenoic acid

      Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5. It also has the trivial name timnodonic acid....
       or EPA (20:5)
    • docosahexaenoic acid
      Docosahexaenoic acid

      Docosahexaenoic acid is an omega-3 fatty acid essential fatty acid. In chemical structure, DHA is a carboxylic acid with a 22-carbon chain and hexa Cis-trans isomerism double bonds; the first double bond is located at the third carbon from the omega end....
       or DHA (22:6)
  • ?-6 fatty acids
    Omega-6 fatty acid

    n-6 fatty acids are a family of unsaturated fat fatty acids which have in common a final carbon?carbon double bond#Bond order in the Fatty acid#Nomenclature position; that is, the sixth bond from the end of the fatty 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....
       or GLA (18:3)
    • 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....
       or DGLA (20:3)
    • 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, ...
       or AA (20:4)


?-9 fatty acids
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....
 are not essential in humans, because humans generally possess all the enzymes required for their synthesis. Exceptions do occur in older people or people with a liver problem that do not completely produce a sufficient amount, and hence many supplement companies market Omega 3-6-9 blends.

Essentiality

Between 1930 and 1950, 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, ...
 and linolenic acid
Alpha-linolenic acid

a-Linolenic acid is an organic compound found in many common Vegetable fats and oils. IUPAC nomenclature of organic chemistry, it is named all-cis-9,12,15-octadecatrienoic acid....
 were termed 'essential' because each was more or less able to meet the growth requirements of rats given fat-free diets. Further research has shown that human metabolism requires both ?-3 and ?-6 fatty acids. To some extent, any ?-3 and any ?-6 can relieve the worst symptoms of fatty acid deficiency. Particular fatty acids are still needed at critical life stages (e.g. lactation) and in some disease states. In nonscientific writing, common usage is that the term
essential fatty acid comprises all the ?-3 or -6 fatty acids. Authoritative sources include the whole families, without qualification. The human body can make some long-chain PUFA (arachidonic acid, EPA and DHA) from lineolate or lineolinate.

Traditionally speaking the LC-PUFA are not essential. See (Cunnane 2003) for a discussion of the current status of the term 'essential'. Because the LC-PUFA are sometimes required, they may be considered "conditionally essential", or not essential to healthy adults.

Mary G. Enig
Mary G. Enig

Mary Gertrude Enig, Ph.D. is a nutritionist who reviews research on and writes articles about the nutritional aspects of fats. Enig attended the University of Maryland, College Park , receiving an M.S....
 has pointed out numerous studies showing the need for omega-3 and omega-6 essential fatty acids in mammalians A 2005 study has shown evidence that gamma-linolenic acid, GLA
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....
 has been shown to inhibit the breast cancer promoting gene of Her2/neu
HER2/neu

HER2/neu stands for "Human Epidermal growth factor Receptor 2" and is a protein giving higher aggressiveness in breast cancers. It is a member of the ErbB protein family, more commonly known as the ErbB....
.

Biologist Ray Peat has pointed out flaws in the studies purportedly showing the need for n-3 and n-6 fats. He notes that so-called EFA deficiencies have sometimes been reversed by adding B vitamins or a fat-free liver extract to the diet. In his view, 'the optional dietary level of the "essential fatty acids" might be close to zero, if other dietary factors were also optimized.'

Essential fatty acids should not be confused with essential oil
Essential oil

An essential oil is a concentrated, hydrophobic liquid containing volatile aroma compounds from plants. They are also known as volatile or ethereal oils, or simply as the "oil of" the plant material from which they were extracted, such as oil of clove....
s, which are "essential" in the sense of being a concentrated essence.

Almost all the polyunsaturated fat in the human diet is from EFA. Some of the food sources of ?-3 and ?-6 fatty acids are fish
Fish

A fish is any marine biology vertebrate animal that is typically ectothermic , covered with scale , and equipped with two sets of paired fins and several unpaired fins....
 and shellfish
Shellfish

Shellfish is a culinary and fisheries term for exoskeleton bearing aquatic invertebrate used as food, including various species of Molluscas, crustaceans, and echinoderms....
, flaxseed (linseed)
Flax

Flax is a member of the genus Linum in the family Linaceae. It is native to the region extending from the eastern Mediterranean region to India and was probably first domesticated in the Fertile Crescent....
, 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....
, soya oil
Soybean

The soybean or soya bean is a species of legume native to East Asia. The plant is classed as an oilseed rather than a Pulse . It is an annual plant that has been used in China for 5,000 years as a food and a component of drugs....
, canola (rapeseed) oil, chia seeds, pumpkin seeds, sunflower seeds, leafy vegetables, and walnut
Walnut

Walnuts are plants in the family Juglandaceae. They are deciduous trees, 10–40 meter s tall , with pinnate leaves 200?900 millimetres long , with 5–25 leaflets; the shoots have chambered pith, a character shared with the wingnut but not the hickory in the same family....
s.

Essential fatty acids play a part in many metabolic processes
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
, and there is evidence to suggest that low levels of essential fatty acids, or the wrong balance of types among the essential fatty acids, may be a factor in a number of illnesses, including osteoporosis
Osteoporosis

Osteoporosis is a disease of bone that leads to an increased risk of bone fracture. In osteoporosis the bone mineral density is reduced, bone microarchitecture is disrupted, and the amount and variety of collagen proteins in bone is altered....
.

Plant sources of ?-3 contain neither eicosapentaenoic acid
Eicosapentaenoic acid

Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5. It also has the trivial name timnodonic acid....
 (EPA) nor docosahexaenoic acid
Docosahexaenoic acid

Docosahexaenoic acid is an omega-3 fatty acid essential fatty acid. In chemical structure, DHA is a carboxylic acid with a 22-carbon chain and hexa Cis-trans isomerism double bonds; the first double bond is located at the third carbon from the omega end....
 (DHA). The human body can (and in case of a purely vegetarian diet often must, unless certain algae
Algae

Algae are a large and diverse group of simple, typically autotrophic organisms, ranging from unicellular to multicellular forms. The largest and most complex marine forms are called seaweeds....
 or supplements derived from them are consumed) convert a-linolenic acid (ALA) to EPA and subsequently DHA. This however requires more metabolic work, which is thought to be the reason that the absorption of essential fatty acids is much greater from animal rather than plant sources (see Fish and plants as a source of Omega-3
Oily fish

Oily fish, oil-rich fish or pelagic fish are those fish which have fish oils throughout the fillet and in the belly cavity around the gut, rather than only in the liver like Whitefish ....
 for more).

The provides a very large and detailed listing of fat contents of animal and vegetable fats, including ?-3 and -6 oils. The National Institutes of Health
National Institutes of Health

The National Institutes of Health is an agency of the United States Department of Health and Human Services and is the primary agency of the United States government responsible for biomedical and health-related research....
's EFA Education group publishes This lists 40 common oils, more tightly focused on EFAs and sorted by n-6:3 ratio. list notable vegetable sources of EFAs as well as commentary and an overview of the biosynthetic pathways involved. Users can interactively search at for the richest food sources of particular EFAs or other nutrients. Careful readers will note that these sources are not in excellent agreement. EFA content of vegetable sources varies with cultivation conditions. Animal sources vary widely, both with the animal's feed and that the EFA makeup varies markedly with fats from different body parts.

Human health

Almost all the polyunsaturated fat
Polyunsaturated fat

In nutrition, polyunsaturated fat is an abbreviation of polyunsaturated fatty acid. That is a fatty acid in which more than one double bond exists within the representative molecule....
s in the human diet are EFAs. Essential fatty acids play an important role in the life and death of cardiac cells.

See also

  • Polyunsaturated fat
    Polyunsaturated fat

    In nutrition, polyunsaturated fat is an abbreviation of polyunsaturated fatty acid. That is a fatty acid in which more than one double bond exists within the representative molecule....
  • Omega-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....
  • Omega-6 fatty acid
    Omega-6 fatty acid

    n-6 fatty acids are a family of unsaturated fat fatty acids which have in common a final carbon?carbon double bond#Bond order in the Fatty acid#Nomenclature position; that is, the sixth bond from the end of the fatty acid....
  • 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....
  • Eicosanoid
    Eicosanoid

    In biochemistry, eicosanoids are lipid signaling made by oxygenation of twenty-carbon essential fatty acids, .They exert complex control over many bodily systems, mainly in inflammation or Immune system, and as messengers in the central nervous system....
    • 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....
    • Leukotriene
      Leukotriene

      Leukotrienes are naturally produced eicosanoid lipid signaling, which may be responsible for the effects of an inflammatory response. Leukotrienes use both autocrine signalling and paracrine signalling to regulate the body's response....
    • Thromboxane
      Thromboxane

      Thromboxane is a member of the family of lipids known as eicosanoids. The two major thromboxanes are thromboxane A2 and thromboxane B2.Thromboxane is named for its role in clot formation ....
  • Nonclassic eicosanoid
    Nonclassic eicosanoid

    Nonclassic eicosanoids are biologically active Lipid signaling made by oxygenation of twenty-carbon fatty acids other than the classic eicosanoids....
  • Endogenous Cannabinoid
    Cannabinoids

    Cannabinoids are a group of terpenephenolic compounds present in Cannabis . The broader definition of cannabinoids refers to a group of substances that are structurally related to tetrahydrocannabinol or that bind to cannabinoid receptors....
  • Essential nutrient
    Essential nutrient

    An essential nutrient is a nutrient required for normal body functioning that cannot be synthesized by the body and thus must be obtained from a Diet source....
  • Essential amino acid
    Essential amino acid

    File:BakedFish.jpgAn essential amino acid or indispensable amino acid is an amino acid that cannot be synthesized de novo synthesis by the organism , and therefore must be supplied in the diet....
  • Fatty acid metabolism
    Fatty acid metabolism

    Fatty acids are an important source of energy for many organisms. Excess glucose can be stored efficiently as fat. Triglycerides yield more than twice as much energy for the same mass as do carbohydrates or proteins....
  • Fatty acid synthase
    Fatty acid synthase

    Fatty acid synthase is enzymatic system composed of 272 kDa multifunctional polypeptide, in which Substrate are handed from one functional domain to the next....
  • Oily fish
    Oily fish

    Oily fish, oil-rich fish or pelagic fish are those fish which have fish oils throughout the fillet and in the belly cavity around the gut, rather than only in the liver like Whitefish ....


External links

  • (public domain resource, and a source for this article)* Chem Phys Lipids. 2003 Nov;126(1):1-27