Arachidonic acid

	WikiDoc Resources for Arachidonic acid
Articles
Most recent articles on Arachidonic acid Most cited articles on Arachidonic acid Review articles on Arachidonic acid Articles on Arachidonic acid in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Arachidonic acid Images of Arachidonic acid Photos of Arachidonic acid Podcasts & MP3s on Arachidonic acid Videos on Arachidonic acid
Evidence Based Medicine
Cochrane Collaboration on Arachidonic acid Bandolier on Arachidonic acid TRIP on Arachidonic acid
Clinical Trials
Ongoing Trials on Arachidonic acid at Clinical Trials.gov Trial results on Arachidonic acid Clinical Trials on Arachidonic acid at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Arachidonic acid NICE Guidance on Arachidonic acid NHS PRODIGY Guidance FDA on Arachidonic acid CDC on Arachidonic acid
Books
Books on Arachidonic acid
News
Arachidonic acid in the news Be alerted to news on Arachidonic acid News trends on Arachidonic acid
Commentary
Blogs on Arachidonic acid
Definitions
Definitions of Arachidonic acid
Patient Resources / Community
Patient resources on Arachidonic acid Discussion groups on Arachidonic acid Patient Handouts on Arachidonic acid Directions to Hospitals Treating Arachidonic acid Risk calculators and risk factors for Arachidonic acid
Healthcare Provider Resources
Symptoms of Arachidonic acid Causes & Risk Factors for Arachidonic acid Diagnostic studies for Arachidonic acid Treatment of Arachidonic acid
Continuing Medical Education (CME)
CME Programs on Arachidonic acid
International
Arachidonic acid en Espanol Arachidonic acid en Francais
Business
Arachidonic acid in the Marketplace Patents on Arachidonic acid
Experimental / Informatics
List of terms related to Arachidonic acid

Arachidonic acid

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

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 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.