Arachidonic acid

Chembox new
Name = Arachidonic acid
ImageFile = AAnumbering.png ImageSize = 350px
IUPACName = "all-cis"-5,8,11,14-eicosatetraenoic acid
Section1 = Chembox Identifiers
CASNo = 506-32-1
SMILES = CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
Section2 = Chembox Properties
Formula = C₂₀H₃₂O₂.
MolarMass = 304.5 g/mol
Density =
MeltingPt = -49.5 °C
BoilingPt = °C (dec.)

Arachidonic acid (AA, sometimes ARA) 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".)cite web
title = Dorland's Medical Dictionary – 'A'
url= http://www.mercksource.com/pp/us/cns/cns_hl_dorlands.jspzQzpgzEzzSzppdocszSzuszSzcommonzSzdorlandszSzdorlandzSzdmd_a_56zPzhtm
accessdate = 2007-01-12]

Chemistry

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.

Biology

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.

ynthesis and cascade

Arachidonic acid is freed from phospholipid molecule by the enzyme phospholipase A2, which cleaves off the fatty acid.

Arachidonic acid is a precursor in the production of eicosanoids:
* the enzymes cyclooxygenase and peroxidase lead to Prostaglandin H2, which in turn is used to produce the prostaglandins, prostacyclin, and thromboxanes.
* the enzyme 5-lipoxygenase leads to 5-HPETE, which in turn is used to produce the leukotrienes.
* arachidonic acid is also used in the biosynthesis of anandamide.

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.

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.cite journal
author=MacDonald M, Rogers Q, Morris J
title=Nutrition of the domestic cat, a mammalian carnivore
url=http://nutr.annualreviews.org/doi/abs/10.1146/annurev.nu.04.070184.002513
journal=Annu Rev Nutr |volume=4 |issue= |pages=521–62 |year=1984
pmid=6380542|accessdate=2007-02-09
doi=10.1146/annurev.nu.04.070184.002513] cite journal |author=Rivers J, Sinclair A, Crawford M |title=Inability of the cat to desaturate essential fatty acids |journal=Nature |url=http://www.nature.com/nature/journal/v258/n5531/abs/258171a0.html |doi=10.1038/258171a0|volume=258 |issue=5531 |pages=171–3 |year=1975 |pmid=1186900]

ee also

* Polyunsaturated fat
* Polyunsaturated fatty acid
* Aspirin - inhibits cyclooxygenase enzyme to prevent the conversion of arachidonic acid to other signal molecules

References

External links

* [http://www.acnp.org/g4/GN401000059/Default.htm Arachidonic Acid] at acnp.org
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