Arachidonic acid

Arachidonic acid
Structural formula of arachidonic acid
Names
Preferred IUPAC name
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid[1]
Other names
5,8,11,14-all-cis-Eicosatetraenoic acid
all-cis-5,8,11,14-Eicosatetraenoic acid
Identifiers
3D model (JSmol)
3DMet
1713889
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.304 Edit this at Wikidata
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:
GHS07: Exclamation mark
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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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Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega−6 fatty acid 20:4(ω−6), or 20:4(5,8,11,14).[2][3] If its precursors or diet contains linoleic acid it is formed by biosynthesis and can be deposited in animal fats. It is a precursor in the formation of leukotrienes, prostaglandins, and thromboxanes.[4]

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.[2][5]

Its name derives from the ancient Greek neologism arachis 'peanut', although peanut oil does not contain any arachidonic acid.[6] Arachidonate is the name of the derived carboxylate anion (conjugate base of the acid), salts, and some esters.

  1. ^ Pubchem. "5,8,11,14-Eicosatetraenoic acid | C20H32O2 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-03-31.
  2. ^ a b "Essential fatty acids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. June 2019. Retrieved 13 May 2024.
  3. ^ "IUPAC Lipid nomenclature: Appendix A: names of and symbols for higher fatty acids". www.sbcs.qmul.ac.uk.
  4. ^ "Dorland's Medical Dictionary – 'A'". Archived from the original on 11 January 2007. Retrieved 2007-01-12.
  5. ^ "Omega-3 fatty acids". Office of Dietary Supplements, US National Institutes of Health. 15 February 2023. Retrieved 13 May 2024.
  6. ^ Truswell A, Choudhury N, Peterson D, Mann J, Agostoni C, Riva E, Giovannini M, Marangoni F, Galli C (1994). "Arachidonic acid and peanut oil". The Lancet. 344 (8928): 1030–1031. doi:10.1016/S0140-6736(94)91695-0. PMID 7999151. S2CID 1522233.