A long-chain ω-3 PUFA
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Docosahexaenoic Acid

Item No. 90310

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid
CAS Number
6217-54-5
Synonyms
  • C22:6 n-3
  • C22:6(4Z,7Z,10Z,13Z,16Z,19Z)
  • Cervonic Acid
  • DHA
  • 4,7,10,13,16,19-Docosahexaenoic Acid
Molecular Formula
C22H32O2
Formula Weight
328.5
Purity
≥98%
Formulation (Request formulation change)
A 250 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.15 M Tris-HCl pH 8.5: >1 mg/mlDMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): <100 µg/ml
SMILES
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
InChi Code
InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChi Key
MBMBGCFOFBJSGT-KUBAVDMBSA-N
Side Chain Carbon Sum
22:6
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 mg

    $54

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    100 mg

    $97

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    250 mg

    $190

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    500 mg

    $297

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    Product Description

    Docosahexaenoic acid (DHA) is a long-chain ω-3 polyunsaturated fatty acid (PUFA) found in fish and algal oils.1 It comprises approximately 40% of total brain PUFAs and is abundant in grey matter and retinal membranes.2 DHA typically represents 0.52-7.5% of human total plasma fatty acids. It is produced from α-linolenic acid (ALA; Item Nos. 90210 | 21910) via a series of desaturase- and elongase-catalyzed reactions, resulting in a docosapentaenoic acid (DPA; Item No. 90165) intermediate, which is elongated, desaturated, and β-oxidized to produce DHA.3 DHA can be liberated from cellular membranes by phospholipase A2 (PLA2) and converted to numerous oxylipins, including specialized pro-resolving mediators (SPMs), which are produced by lipoxygenases and include D-series protectins and resolvins, as well as maresins, that regulate host defense and the resolution of inflammation.4 DHA has roles in several physiological and pathological processes, including neural development, cardiovascular diseases, obesity, and inflammation.3,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kuratko, C.N., and Salem, N., Jr. Biomarkers of DHA status. Prostaglandins Leukot. Essent. Fatty Acids 81(2-3), 111-118 (2009).

    2. Lacombe, R.J.S., Chouinard-Watkins, R., and Bazinet, R.P. Brain docosahexaenoic acid uptake and metabolism. Mol. Aspects Med. 64, 109-134 (2018).

    3. Calder, P.C. Docosahexaenoic acid. Ann. Nutr. Metab. 69(Suppl 1), 7-21 (2016).

    4. Basil, B.C., and Levy, B.D. Specialized pro-resolving mediators: Endogenous regulators of infection and inflammation. Nat. Rev. Immunol. 16(1), 51-67 (2016).

    5. Arnoldussen, I.A.C., and Kiliaan, A.J. Impact of DHA on metabolic diseases from womb to tomb. Mar. Drugs 12(12), 6190-6212 (2014).

    Product Citations

    Zhang, L.J., Salekeen, R., Soto-Palma, C., et al. Article polyunsaturated lipid senolytics exploit a ferroptotic vulnerability in senescent cells. Cell Press Blue 1(1), 100004 (2026).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. The FASEB Journal 35(6), e21666 (2021).

    Roberts, L.M., Schwarz, B., Speranza, E., et al. Pulmonary infection induces persistent, pathogen-specific lipidomic changes influencing trained immunity. iScience 24(9), 103025 (2021).

    Low, Y.L., Pan, Y., Short, J.L., et al. Profiling the expression of fatty acid-binding proteins and fatty acid transporters in mouse microglia and assessing their role in docosahexaenoic acid-d5 uptake. Prostaglandins Leukot. Essent. Fatty Acids 171:102303, (2021).

    Zou, Y., Li, H., Graham, E.T., et al. Cytochrome P450 oxidoreductase contributes to phospholipid peroxidation in ferroptosis. Nat. Chem. Biol. 16(3), 302-309 (2020).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Katsnelson, G., and Ceddia, R.B. Docosahexaenoic and eicosapentaenoic fatty acids differentially regulate glucose and fatty acid metabolism in L6 rat skeletal muscle cells. Am. J. Physiol. Cell Physiol. 319(6), C1120-C1129 (2020).

    Cao, H., Li, M.-Y., Li, G., et al. Retinoid X receptor α regulates DHA-dependent spinogenesis and functional synapse formation in vivo. Cell Rep. 31(7), 107649 (2020).

    Brouwers, H., Jónasdóttir, H.S., Kuipers, M.E., et al. Anti-inflammatory and proresolving effects of the omega-6 polyunsaturated fatty acid adrenic acid. J. Immunol. 205(10), 2840-2849 (2020).

    Lumbroso, D., Soboh, S., Maimon, A., et al. Macrophage-derived protein S facilitates apoptotic polymorphonuclear cell clearance by resolution phase macrophages and supports their reprogramming. Front. Immunol. 9, 358 (2018).

    Dalli, J., Colas, R.A., Walker, M.E., et al. Lipid Mediator Metabolomics via LC-MS/MS Profiling and Analysis. Clinical Metabolomics 59-72 (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).

    Deng, B.-Q., Luo, Y., Kang, X., et al. Epoxide metabolites of arachidonate and docosahexaenoate function conversely in acute kidney injury involved in GSK3β signaling. Proc. Natl. Acad. Sci. USA 114(47), 12608-12613 (2017).

    Caires, R., Sierra-Valdez, F.J., Millet, J.R.M., et al. Omega-3 fatty acids modulate TRPV4 function through plasma membrane remodeling. Cell Reports 21, 245-258 (2017).

    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).

    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).

    Huang, C.B., and Ebersole, J.L. A novel bioactivity of omega-3 polyunsaturated fatty acids and their ester derivatives. Mol. Oral Microbiol. 25(1), 75-80 (2010).

    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).

    Yuan, C., Sidhu, R.S., Kuklev, D.V., et al. Cyclooxygenase allosterism, fatty acid-mediated cross-talk between monomers of cyclooxygenase homodimers. The Journal of Biological Chemisty 284(15), 10046-10055 (2009).