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Topic summary

Arachidonic acid

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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
3D model (JSmol)
1713889 ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.007.304EC Number
  • 208-033-4
58972
KEGG
MeSHArachidonic+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)
    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
  • CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
Properties C20H32O2Molar mass304.474 g·mol Density0.922 g/cm Melting point−49 °C (−56 °F; 224 K) Boiling point169 to 171 °C (336 to 340 °F; 442 to 444 K) at 0.15 mmHg log P6.994 Acidity (pKa) 4.752 Hazards GHS labelling: WarningH302, H312, H315, H319, H332, H335P261, 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, P501NFPA 704 (fire diamond)
1
1
0
Flash point113 °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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Arachidonic acid (AA, sometimes ARA) is a polyunsaturatedomega−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.

It was named after the similarly structured Arachidic acid, a constituent of peanut oil whose name in turn derives from the ancient Greekneologismarachis 'peanut'. Peanut oil does not contain any arachidonic acid, itself. Arachidonate is the name of the derived carboxylate anion (conjugate base of the acid), salts, and some esters.

Wikipedia source