An ω-6 PUFA; precursor of eicosanoids
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Arachidonic Acid

Item No. 90010

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5Z,8Z,11Z,14Z-eicosatetraenoic acid
CAS Number
506-32-1
Synonyms
  • AA
  • FA 20:4
Molecular Formula
C20H32O2
Formula Weight
304.5
Purity
≥98%
Formulation (Request formulation change)
A 250 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 1.7 mg/mlDMF: 100 mg/mlDMSO: 100 mg/mlEthanol: Miscible
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChi Code
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-
InChi Key
YZXBAPSDXZZRGB-DOFZRALJSA-N
Side Chain Carbon Sum
20:4
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 mg

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    250 mg

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    500 mg

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    Product Description

    Arachidonic acid is an essential fatty acid and a precursor for all prostaglandins, thromboxanes, and leukotrienes. Virtually all cellular arachidonic acid is esterified in membrane phospholipids where its presence is tightly regulated through multiple interconnected pathways.1 Free arachidonic acid is a transient, critical substrate for the biosynthesis of eicosanoid second messengers. Receptor-stimulated release, metabolism, and re-uptake of free arachidonate are all important aspects of cell signaling and inflammation.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nixon, A.B., Greene, D.G., and Wykle, R.L. Comparison of acceptor and donor substrates in the CoA-independent transacylase reaction in human neutrophils. Biochim. Biophys. Acta 1300(3), 187-196 (1996).

    2. Burgoyne, R.D., and Morgan, A. The control of free arachidonic acid levels. Trends Biochem. Sci. 15(10), 365-366 (1990).

    Product Citations

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    Anthonymuthu, T.S., Kenny, E.M., Shrivastava, I., et al. Empowerment of 15-lipoxygenase catalytic competence in selective oxidation of membrane ETE-PE to ferroptotic death signals, HpETE-PE. J. Am. Chem. Soc. 140(51), 17835-17839 (2018).

    Lahvic, J.L., Ammerman, M., Li, P., et al. Specific oxylipins enhance vertebrate hematopoiesis via the receptor GPR132. PNAS 115(37), 9252-9257 (2018).

    Archambault, A.-S., Turcotte, C., Martin, C., et al. Comparison of eight 15-lipoxygenase (LO) inhibitors on the biosynthesis of 15-LO metabolites by human neutrophils and eosinophils. PLoS One 13(8), e0202424 (2018).

    Mildenberger, J., Johansson, I., Sergin, I., et al. N-3 PUFAs induce inflammatory tolerance by formation of KEAP1-containing SQSTM1/p62-bodies and activation of NFE2L2. Autophagy 13(10), 1664-1678 (2017).

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    Hinman, A., Holst, C.R., Latham, J.C., et al. Vitamin E hydroquinone is an endogenous regulator of ferroptosis via redox control of 15-lipoxygenase. PLoS One 13(8), e0201369 (2018).

    Shin, S.K., Kim, J.H., Lee, J.H., et al. Docosahexaenoic acid-mediated protein aggregates may reduce proteasome activity and delay myotube degradation during muscle atrophy in vitro. Exp. Mol. Med. 49(1), e287 (2017).

    Yamamoto, T., Matsui, H., Yamaji, K., et al. Narrow-spectrum inhibitors targeting an alternative menaquinone biosynthetic pathway of Helicobacter pylori. J. Infect. Chemother. 22(9), 587-595 (2016).

    Zhao, X., Lu, W., Song, C., et al. Detection of mammalian 5-lipoxygenase activity using the fluorescent probe dihydrorhodamine 123. Eur. J. Lipid Sci. Technol. 116, 119-125 (2014).

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    Jovanović, V., Aziz, N.A., Lim, Y.T., et al. Lipid anti-lipid antibody responses correlate with disease activity in systemic lupus erythematosus. PLoS one 8(2), e55639 (2013).

    Lucas, D., Goulitquer, S., Marienhagen, J., et al. Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450. J. Lipid Res. 51(5), 1125-1133 (2010).

    Sun, P., Lin, D.H., Yue, P., et al. High potassium intake enhances the inhibitory effect of 11,12-EET on ENaC. J. Am. Soc. Nephrol. 21(10), 1667-1677 (2010).

    Vance, R.E., Hong, S., Gronert, K., et al. The opportunistic pathogen Pseudomonas aeruginosa carries a secretable arachidonate 15-lipoxygenase. Proc. Natl. Acad. Sci. USA 101(7), 2135-2139 (2004).

    Qi, H.-Y., Daniels, M.P., Liu, Y., et al. A cytosolic phospholipase A2-initiated lipid mediator pathway induces autophagy in macrophages. J. Immunol. 187(10), 5286-5292 (2011).

    Rouzer, C.A., and Marnett, L.J. Glycerylprostaglandin synthesis by resident peritoneal macrophages in response to a zymosan stimulus. The Journal of Biological Chemisty 280(29), 26690-26700 (2005).

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