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).^[2]^[3] 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.

^ Pubchem. "5,8,11,14-Eicosatetraenoic acid | C20H32O2 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-03-31.
^ ^a ^b "Essential fatty acids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. June 2019. Retrieved 13 May 2024.
^ "IUPAC Lipid nomenclature: Appendix A: names of and symbols for higher fatty acids". www.sbcs.qmul.ac.uk.
^ "Dorland's Medical Dictionary – 'A'". Archived from the original on 11 January 2007. Retrieved 2007-01-12.
^ "Omega-3 fatty acids". Office of Dietary Supplements, US National Institutes of Health. 15 February 2023. Retrieved 13 May 2024.
^ 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.

[1] Pubchem. "5,8,11,14-Eicosatetraenoic acid | C20H32O2 - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2016-03-31.

[lpi-2] "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.

[Dorland-4] "Dorland's Medical Dictionary – 'A'". Archived from the original on 11 January 2007. Retrieved 2007-01-12.

[ods-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.

[1]

[2]

[3]

[4]

[5]

[6]