Arachidonic acid

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Arachidonic acid
Image:AAnumbering.png
IUPAC name all-cis-5,8,11,14-eicosatetraenoic acid
Identifiers
CAS number 506-32-1
SMILES CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
Properties
Molecular formula C20H32O2.
Molar mass 304.5 g/mol
Melting point

-49.5 °C

Boiling point

°C (dec.)

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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]

Contents

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.
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

Image:Steaks.jpg
Arachidonic acid in the human body comes from dietary animal sources—meat, eggs, dairy—or is synthesized from linoleic 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.[1][1]

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

References


See also

External links

de:Arachidonsäurefr:Acide arachidonique

it:Acido arachidonico lv:Arahidonskābe nl:Arachidonzuur ja:アラキドン酸sl:Arahidonska kislina fi:Arakidonihappo

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