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 Neo-Latin word 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
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
  • 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).
N verify (what is YN ?)
Infobox references
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