Arachidonic acid

Arachidonic acid
Names
	Preferred 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
Identifiers
CAS Number	506-32-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1713889
ChEBI	CHEBI:15843 ;
ChEMBL	ChEMBL15594 ;
ChemSpider	392692 ;
DrugBank	DB04557 ;
ECHA InfoCard	100.007.304
EC Number	208-033-4;
Gmelin Reference	58972
IUPHAR/BPS	2391;
KEGG	C00219 ;
MeSH	Arachidonic+acid
PubChem CID	444899;
RTECS number	CE6675000;
UNII	27YG812J1I ;
CompTox Dashboard (EPA)	DTXSID4040420 ;
	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) Key: YZXBAPSDXZZRGB-UHFFFAOYSA-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	304.474 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
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)	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). verify (what is ?) Infobox references

Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega−6 fatty acid 20:4(ω−6), or 20:4(5,8,11,14). It is a precursor in the formation of leukotrienes, prostaglandins, and thromboxanes.

Together with omega−3 fatty acids and other omega−6 fatty acids, arachidonic acid provides energy for body functions, contributes to cell membrane structure, and participates in the synthesis of eicosanoids, which have numerous roles in physiology as signaling molecules.

Its name derives from the ancient Greek neologism arachis 'peanut', although peanut oil does not contain any arachidonic acid. Arachidonate is the name of the derived carboxylate anion (conjugate base of the acid), salts, and some esters.