An internal standard for the quantification of RvD2
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Resolvin D2-d5

Item No. 11184

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7S,16R,17S-trihydroxy-4Z,8E,10Z,12E,14E,19Z-21,21’,22,22,22-d5 docosahexaenoic acid
CAS Number
1881277-33-3
Synonyms
  • 7(S),16(R),17(S)-Resolvin D2-d5
  • RvD2-d5
Molecular Formula
C22H27D5O5
Formula Weight
381.5
Purity
≥99% deuterated forms (d1-d5)
Formulation
A 100 µg/ml solution in ethanol
λmax
289, 302, 316 nm
SMILES
[2H]C([2H])(C([2H])([2H])[2H])/C=C\C[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)C/C=C\CCC(O)=O
InChi Code
InChI=1S/C22H32O5/c1-2-3-9-16-20(24)21(25)17-12-7-5-4-6-10-14-19(23)15-11-8-13-18-22(26)27/h3-12,14,17,19-21,23-25H,2,13,15-16,18H2,1H3,(H,26,27)/b6-4-,7-5+,9-3-,11-8-,14-10+,17-12+/t19-,20+,21-/m1/s1/i1D3,2D2
InChi Key
IKFAUGXNBOBQDM-XNSNRJMHSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    10 µg

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    Product Description

    Resolvin D2-d5 (RvD2-d5) is intended for use as an internal standard for the quantification of resolvin D2 (Item No. 10007279) by GC- or LC-MS. Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).1 In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state.2 Resolvin D2 is produced physiologically from the sequential oxygenation of DHA by 15- and 5-lipoxygenase and functions to dampen excessive neutrophil trafficking to sites of inflammation.3 It reduces zymosan-stimulated PMN infiltration by 70% at doses as low as 10 pg per mouse and significantly reduces PAF-stimulated leukocyte adherence and emigration at 1 nM.3 Also, by stimulating nitric oxide production, resolvin D2 dose dependently decreases leukocyte-endothelial interactions. In a murine model of sepsis, resolvin D2 reduces leukocyte and PMN infiltration, decreases production of pro-inflammatory cytokines, and promotes phagocyte-mediated bacterial clearance.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hong, S., Gronert, K., Devchand, P.R., et al. Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation. The Journal of Biological Chemisty 278(17), 14677-14687 (2003).

    2. Ariel, A., and Serhan, C.N. Resolvins and protectins in the termination program of acute inflammation. Trends Immunol. 28(4), 176-183 (2007).

    3. Spite, M., Norling, L.V., Summers, L., et al. Resolvin D2 is a potent regulator of leukocytes and controls microbial sepsis. Nature 461(7268), 1287-1291 (2009).

    Product Citations

    Archambault, A.-S., Brassard, J., Bernatchez, É., et al. Human and mouse eosinophils differ in their ability to biosynthesize eicosanoids, docosanoids, the endocannabinoid 2-arachidonoyl-glycerol and its congeners. Cells 11(1), 141 (2022).

    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).

    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).

    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).

    Norris, P.C., Libreros, S., and Serhan, C.N. Resolution metabolomes activated by hypoxic environment. Sci. Adv. 5(10), eaax4895 (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).

    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).

    English, J.T., Norris, P.C., Hodges, R.R., et al. Identification and profiling of specialized pro-resolving mediators in human tears by lipid mediator metabolomics. Prostaglandins Leukot. Essent. Fatty Acids 117, 17-27 (2017).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).