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Arachidonic acid
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| 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)
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| 3DMet | |||
| 1713889 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.007.304 | ||
| EC Number |
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| 58972 | |||
| KEGG | |||
| MeSH | Arachidonic+acid | ||
PubChem CID
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| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA)
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| 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: | |||
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| 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) | |||
| Flash point | 113 °C (235 °F; 386 K) | ||
| Related compounds | |||
Related compounds
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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.
- ^ 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.
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