An internal standard for the quantification of DHA
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Docosahexaenoic Acid-d5

Item No. 10005057

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic-21,21,22,22,22-d5 acid
CAS Number
1197205-71-2
Synonyms
  • C22:6 n-3-d5
  • C22:6(4Z,7Z,10Z,13Z,16Z,19Z)-d5
  • Cervonic Acid-d5
  • DHA-d5
  • 4,7,10,13,16,19-Docosahexaenoic Acid-d5
  • FA 22:6-d5
Molecular Formula
C22H27D5O2
Formula Weight
333.5
Purity
≥99% deuterated forms (d1-d5)
Formulation
A 500 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): .1 mg/ml
SMILES
[2H]C([2H])([2H])C([2H])([2H])/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-/i1D3,2D2
InChi Key
MBMBGCFOFBJSGT-RPBOKJFVSA-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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Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    50 µg

    $84

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    100 µg

    $151

    Add

    500 µg

    $460

    Add

    1 mg

    $586

    Add
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    Product Description

    Docosahexaenoic acid-d5 (DHA-d5) is intended for use as an internal standard for the quantification of DHA (Item No. 90310) by GC- or LC-MS. 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

    von Krusenstiern, A.N., Robson, R.N., Qian, N., et al. Identification of essential sites of lipid peroxidation in ferroptosis. Nat. Chem. Biol. 19(6), 719-730 (2023).

    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).

    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).

    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).

    Ochiai, Y., Uchida, Y., Tachikawa, M., et al. Amyloid beta25-35 impairs docosahexaenoic acid efflux by down-regulating fatty acid transport protein 1 (FATP1/SLC27A1) protein expression in human brain capillary endothelial cells. J. Neurochem. 150(4), 385-401 (2019).