A DHA derivative with anti-inflammatory and anti-platelet activity
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10(S),17(S)-DiHDHA

Item No. 10008128

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
10(S),17(S)-dihydroxy-4Z,7Z,11E,13Z,15E,19Z-docosahexaenoic acid
CAS Number
871826-47-0
Synonyms
  • 10(S),17(S)-DiHDoHE
  • PDX
  • Protectin DX
Molecular Formula
C22H32O4
Formula Weight
360.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 1 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS (pH 7.2): 0.5 mg/ml
λmax
270 nm
SMILES
CC/C=C\C[C@H](O)/C=C/C=C\C=C\[C@@H](O)C/C=C\C/C=C\CCC(O)=O
InChi Code
InChI=1S/C22H32O4/c1-2-3-10-15-20(23)17-12-8-9-13-18-21(24)16-11-6-4-5-7-14-19-22(25)26/h3,5-13,17-18,20-21,23-24H,2,4,14-16,19H2,1H3,(H,25,26)/b7-5-,9-8-,10-3-,11-6-,17-12+,18-13+/t20-,21-/m0/s1
InChi Key
CRDZYJSQHCXHEG-XLBFCUQGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $201

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    50 µg

    $357

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    100 µg

    $674

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    Product Description

    10(S),17(S)-DiHDHA is a DHA metabolite, also referred to as protectin DX (PDX).1 It is produced by an apparent double lipoxygenase (LO)-mediated reaction in murine peritonitis exudates, in suspensions of human leukocytes, or by soybean 15-LO incubated with DHA.2,1 It differs from protectin D1 with respect to the stereochemistry of the C-10 hydroxyl and the double bond configuration at the 13 and 15 positions. 10(S),17(S)-DiHDHA blocks neutrophil infiltration in murine peritonitis by 20-25% at a dose of 1 ng/mouse.2 It also inhibits platelet activation by both impairing thromboxane (TX) synthesis and TX receptor activation.1,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, P., Fenet, B., Michaud, S., et al. Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation. FEBS Lett. 583, 3478-3484 (2009).

    2. Serhan, C.N., Gotlinger, K., Hong, S., et al. Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: Assignments of dihydroxy-containing docosatrienes. J. Immunol. 176(3), 1848-1859 (2006).

    3. Chen, P., Véricel, E., Lagarde, M., et al. Poxytrins, a class of oxygenated products from polyunsaturated fatty acids, potently inhibit blood platelet aggregation. The FASEB Journal 25, 382-388 (2011).

    Product Citations

    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).

    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).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Kutzner, L., Rund, K.M., Ostermann, A.I., et al. Development of an optimized LC-MS method for the detection of specialized pro-resolving mediators in biological samples. Front. Pharmacol. 10, 169 (2019).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (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).