Arachidonic acid

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 structurally related to the saturated arachidic acid found in cupuaçu butter. Its name derives from the ancient Greek neologism arachis (peanut), but peanut oil does not contain any 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; Arachidonate
Identifiers
3D model (JSmol)
3DMet
1713889
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.304
EC Number
  • 208-033-4
58972
KEGG
MeSH Arachidonic+acid
PubChem CID
RTECS number
  • CE6675000
UNII
  • 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
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:
Warning
H302, H312, H315, H319, H332, H335
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).
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Infobox references
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