Arachidonic acid

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Arachidonic acid
IUPAC name all-cis-5,8,11,14-eicosatetraenoic acid
Identifiers
3D model (JSmol)
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Properties
C20H32O2.
Molar mass 304.5 g/mol
Melting point
Boiling point
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Overview

Arachidonic acid (AA) is an omega-6 fatty acid 20:4(ω-6). It is the counterpart to the saturated arachidic acid found in peanut oil, (L. arachis – peanut.)[1]

Chemical characteristics

Chemically, arachidonic acid is a carboxylic acid with a 20-carbon chain and four cis double bonds; the first double bond is located at the sixth carbon from the omega end.

Some chemistry sources define 'arachidonic acid' to designate any of the eicosatetraenoic acids. However, almost all writings in biology, medicine and nutrition limit the term to all-cis 5,8,11,14-eicosatetraenoic acid.

Biological role

Arachidonic acid is a polyunsaturated fatty acid that is present in the phospholipids (especially phosphatidylethanolamine, phosphatidylcholine and phosphatidylinositides) of membranes of the body's cells, and is abundant in the brain.

It is also involved in cellular signaling as a second messenger.

It is the source of several other molecules with specific roles, as described in the next section.

Synthesis and cascade

Eicosanoid synthesis.

Arachidonic acid is freed from phospholipid molecule by the enzyme phospholipase A2, which cleaves off the fatty acid precursor (usually linoleic acid).

Arachidonic acid is a precursor in the production of eicosanoids:

The production of these derivatives, and their action in the body, are collectively known as the arachidonic acid cascade; see essential fatty acid interactions for more details.

Arachidonic acid as an essential fatty acid

Arachidonic acid is one of the essential fatty acids required by most mammals. Some mammals lack the ability to—or have a very limited capacity to—convert linoleic acid into arachidonic acid, making it an essential part of their diet. Since little or no arachidonic acid is found in plants, such animals are obligate carnivores; the cat is a common example.[2][3]

For a more detailed discussion of the term 'essential', see Essential fatty acid – What is "essential"?

References

  1. "Dorland's Medical Dictionary – 'A'". Retrieved 2007-01-12.
  2. MacDonald M, Rogers Q, Morris J (1984). "Nutrition of the domestic cat, a mammalian carnivore". Annu Rev Nutr. 4: 521–62. PMID 6380542. Retrieved 2007-02-09.
  3. Rivers J, Sinclair A, Crawford M (1975). "Inability of the cat to desaturate essential fatty acids". Nature. 258 (5531): 171–3. doi:10.1038/258171a0. PMID 1186900.

See also

External links

de:Arachidonsäure it:Acido arachidonico lv:Arahidonskābe nl:Arachidonzuur sl:Arahidonska kislina fi:Arakidonihappo



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