Arachidonic acid metabolism

Arachidonic acid

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
CAS Number	506-32-1 Y
3D model (JSmol)	Interactive image
3DMet	B00061
Beilstein Reference	1713889
ChEBI	CHEBI:15843 Y
ChemSpider	392692 Y
DrugBank	DB04557 N
ECHA InfoCard	100.007.304
EC Number	208-033-4
IUPHAR/BPS	2391
KEGG	C00219 N
MeSH	Arachidonic+acid
PubChem CID	444899
RTECS number	CE6675000
UNII	27YG812J1I Y
InChI InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22) N Key: YZXBAPSDXZZRGB-UHFFFAOYSA-N N InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15- Key: YZXBAPSDXZZRGB-DOFZRALJSA-N
SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
Properties
Chemical formula	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R-phrases (outdated)	R19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	1 1 0
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).
N  (what is YN ?)
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).

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.