A specialized pro-resolving mediator
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Isomer(s)
10011453Lipoxin A5
Labeled Version(s)
10009854Resolvin E1-d4
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Resolvin E1

Item No. 10007848

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5S,12R,18R-trihydroxy-6Z,8E,10E,14Z,16E-eicosapentaenoic acid
CAS Number
552830-51-0
Synonyms
  • RvE1
  • 5S,12R,18R-trihydroxy-EPA
  • 5S,12R,18R-trihydroxy-6Z,8E,10E,14Z,16E-EPA
  • 5,12,18R-triHEPE
Molecular Formula
C20H30O5
Formula Weight
350.5
Purity
≥95%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): .05 mg/ml
λmax
272 nm
SMILES
O[C@@H](CCCC(O)=O)/C=C\C=C\C=C\[C@H](O)C/C=C\C=C\[C@H](O)CC
InChi Code
InChI=1S/C20H30O5/c1-2-17(21)11-8-5-9-14-18(22)12-6-3-4-7-13-19(23)15-10-16-20(24)25/h3-9,11-13,17-19,21-23H,2,10,14-16H2,1H3,(H,24,25)/b4-3+,9-5-,11-8+,12-6+,13-7-/t17-,18+,19-/m1/s1
InChi Key
AOPOCGPBAIARAV-OTBJXLELSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    10 µg

    $153

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    25 µg

    $345

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    50 µg

    $651

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    100 µg

    $1,071

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    Product Description

    Resolvin E1 (RvE1) is a member of the specialized pro-resolving mediator (SPM) family of bioactive lipids.1 It is produced from eicosapentaenoic acid (EPA; Item No. 90110 | 90110.1 | 21908) via an 18-HEPE epoxide intermediate, which is formed by aspirin-acetylated COX-2-mediated oxidation of EPA and 5-lipoxygenase (5-LO), by leukotriene A4 (LTA4) hydrolase in human polymorphonuclear (PMN) neutrophils. RvE1 activates chemokine-like receptor 1 (CMKLR1; EC50 = 0.137 nM in a reporter assay). RvE1 (20 ng/animal) inhibits increases in inflammatory exudate neutrophil infiltration in a mouse model of peritonitis induced by zymosan A (Item No. 21175). It increases survival and prevents decreases in colon length in a mouse model of TNBS-induced colitis when administered at a dose of 50 µg/kg.2 RvE1 (50 µg/kg) inhibits ovalbumin-induced increases in eosinophil and total cell numbers, as well as IL-13 and IgE levels in bronchoalveolar lavage fluid (BALF) in an ovalbumin-sensitized mouse model of asthma.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Oh, S.F., Pillai, P.S., Recchiuti, A., et al. Pro-resolving actions and stereoselective biosynthesis of 18S E-series resolvins in human leukocytes and murine inflammation. J. Clin. Invest. 121(2), 569-581 (2011).

    2. Arita, M., Yoshida, M., Hong, S., et al. Resolvin E1, an endogenous lipid mediator derived from omega-3 eicosapentaenoic acid, protects against 2,4,6-trinitrobenzene sulfonic acid-induced colitis. Proc. Natl. Acad. Sci. USA 102(21), 7671-7676 (2005).

    3. Aoki, H., Hisada, T., Ishizuka, T., et al. Resolvin E1 dampens airway inflammation and hyperresponsiveness in a murine model of asthma. Biochem. Biophys. Res. Commun. 367(2), 509-515 (2008).

    Product Citations

    Li, J., Xiao, Y., Zhang, Y., et al. Pulmonary delivery of specialized pro-resolving mediators-based nanotherapeutics attenuates pulmonary fibrosis in preclinical animal models. ACS Nano 17(16), 15354-15370 (2023).

    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).

    Dakin, S.G., Colas, R.A., Wheway, K., et al. Proresolving mediators LXB4 and RevE1 regulate inflammation in stromal cells from patients with shoulder tendon tears. Am. J. Pathol. 189(11), 2258-2268 (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).

    Lin, N., Shay, J.E.S., Xie, H., et al. Myeloid cell hypoxia-inducible factors promote resolution of inflammation in experimental colitis. Front. Immunol. 9(2565), (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).