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Arachidonic acid metabolism

Arachidonic acid
Structural formula of arachidonic acid
Arachidonic acid spacefill.png
Arachidonic acid2.png
Names
IUPAC name
(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid
Systematic IUPAC name
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid
Other names
5,8,11,14-all-cis-Eicosatetraenoic acid; all-cis-5,8,11,14-Eicosatetraenoic acid; Arachidonate
Identifiers
3D model (JSmol)
3DMet B00061
1713889
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.007.304
EC Number 208-033-4
KEGG
MeSH Arachidonic+acid
PubChem CID
RTECS number CE6675000
UNII
Properties
C20H32O2
Molar mass 304.47 g·mol−1
Density 0.922 g/cm3
Melting point −49 °C (−56 °F; 224 K)
Boiling point 169 to 171 °C (336 to 340 °F; 442 to 444 K) at 0.15 mmHg
log P 6.994
Acidity (pKa) 4.752
Hazards
R-phrases (outdated) R19
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related compounds
Eicosatetraenoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6). It is structurally related to the saturated arachidic acid found in Cupuaçu butter (L. arachis – peanut).

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In chemical structure, 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.

Arachidonic acid is a polyunsaturated fatty acid present in the phospholipids (especially phosphatidylethanolamine, phosphatidylcholine, and phosphatidylinositides) of membranes of the body's cells, and is abundant in the brain, muscles, and liver. Skeletal muscle is an especially active site of arachidonic acid retention, accounting for roughly 10-20% of the phospholipid fatty acid content on average.


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Wikipedia

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