An ω-3 endocannabinoid epoxide
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

(±)17(18)-EpETE-Ethanolamide

Item No. 25920

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
16-(3-ethyl-2-oxiranyl)-N-(2-hydroxyethyl)-5Z,8Z,11Z,14Z-hexadecatetraenamide
CAS Number
2123491-23-4
Synonyms
  • 17,18-EEQ-EA
  • (±)17,18-EEQ-Ethanolamide
  • (±)17(18)-EpETE-EA
  • 17,18-epoxy-Eicosatetraenoic Acid Ethanolamide
Molecular Formula
C22H35NO3
Formula Weight
361.5
Purity
≥98%
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 30 mg/ml
SMILES
CCC1C(O1)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCO)=O
InChi Code
InChI=1S/C22H35NO3/c1-2-20-21(26-20)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-22(25)23-18-19-24/h3,5-6,8-9,11-12,14,20-21,24H,2,4,7,10,13,15-19H2,1H3,(H,23,25)/b5-3-,8-6-,11-9-,14-12-
InChi Key
PVTVBNICUOQEDT-JPURVOHMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Recommended Products

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.

Download most recent Certificate of Analysis for this product

    25 µg

    $46

    Add

    50 µg

    $86

    Add

    100 µg

    $160

    Add

    500 µg

    $707

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    (±)17(18)-EpETE-Ethanolamide is an ω-3 endocannabinoid epoxide.1 It is formed from the endocannabinoid eicosapentaenoic ethanolamide (EPEA) via cytochrome P450 (CYP) epoxygenases and hydrolyzed by soluble epoxide hydrolase (sEH) and fatty acid amide hydrolase (FAAH). It is endogenously produced in LPS-stimulated BV-2 microglia cells and in BV-2 microglia cells supplemented with EPEA, an effect that can be reduced by the CYP inhibitor ketoconazole. (±)17(18)-EpETE-ethanolamide decreases IL-6 and nitrite production induced by LPS in BV-2 microglia and increases the production of IL-10. It inhibits platelet aggregation induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) when used at a concentration of 50 µM but not aggregation induced by ADP (Item Nos. 16778 | 21121), collagen, or ristocetin. It also induces relaxation of preconstricted bovine coronary arteries (ED50 = 1.1 µM) and inhibits VEGF-stimulated tubulogenesis in human microvascular endothelial cells (HMVECs). (±)17(18)-EpETE-ethanolamide is the predominant EPEA metabolite found in rat brain, and it has also been found in rat heart, kidney, spleen, and liver, as well as in pig brain. It activates cannabinoid receptor 1 (CB1) and CB2 with EC50 values of 18.5 and 1.4 nM, respectively, in a β-arrestin recruitment assay.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McDougle, D.R., Watson, J.E., Abdeen, A.A., et al. Anti-inflammatory ω-3 endocannabinoid epoxides. Proc. Natl. Acad. Sci. USA 114(30), E6034-E6043 (2017).