Epoxygenase metabolite of EPA
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(±)11(12)-EpETE

Item No. 10462

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-(11S,12R)-epoxy-5Z,8Z,14Z,17Z- eicosatetraenoic acid
CAS Number
504435-15-8
Synonyms
  • (±)11,12-EEQ
  • (±)11,12-Epoxyeicosatetraenoic Acid
Molecular Formula
C20H30O3
Formula Weight
318.5
Purity
≥98%
Formulation (Request formulation change)
A 100 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
CC/C=C\C/C=C\C[C@@H]1[C@@H](O1)C/C=C\C/C=C\CCCC(O)=O.CC/C=C\C/C=C\C[C@H]2[C@H](O2)C/C=C\C/C=C\CCCC(O)=O
InChi Code
InChI=1S/2C20H30O3/c2*1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h2*3-4,6,8-10,12-13,18-19H,2,5,7,11,14-17H2,1H3,(H,21,22)/b2*4-3-,8-6-,12-9-,13-10-/t2*18-,19+/m10/s1
InChi Key
TUBYWKPEWIJKHE-KVCUORNDSA-N
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

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    25 µg

    $53

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    50 µg

    $98

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    100 µg

    $185

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    500 µg

    $813

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    Product Description

    Eicosapentaenoic acid (EPA; Item No. 90110) is converted to epoxyeicosatetraenoic acids (EpETE) by several cytochrome P450 isoforms.1 The major product of this epoxygenase pathway, (±)17(18)-EpETE (Item No. 50861), relaxes vascular and airway smooth muscle by binding large conductance Ca2+-activated K+ (BKCa) channels by directly interacting with BKα channel subunits.2,3,4 (±)11(12)-EpETE is an epoxygenase pathway product produced from EPA by CYP450 both in vitro and in vivo.1,5 The biological actions and physiological effects of this epoxide remain to be determined.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Barbosa-Sicard, E., Markovic, M., Honeck, H., et al. Eicosapentaenoic acid metabolism by cytochrome P450 enzymes of the CYP2C subfamily. Biochem. Biophys. Res. Commun. 329, 1275-1281 (2005).

    2. Lauterbach, B., Barbosa-Sicard, E., Wang, M.H., et al. Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators. Hypertension 39(2 Pt. 2), 609-613 (2002).

    3. Hercule, H.C., Salanova, B., Essin, K., et al. The vasodilator 17,18-epoxyeicosatetraenoic acid targets the pore-forming BKα channel subunit in rodents. Exp. Physiol. 92(6), 1067-1076 (2007).

    4. Morin, C., Sirois, M., Echave, V., et al. Relaxing effects of 17(18)-EpETE on arterial and airway smooth muscles in human lung. Am. J. Physiol. Lung Cell. Mol. Physiol. 296, L130-L139 (2009).

    5. Arnold, C., Markovic, M., Blossey, K., et al. Arachidonic acid-metabolizing cytochrome P450 enzymes are targets of omega-3 fatty acids. The Journal of Biological Chemisty 285(43), 32720-32733 (2010).

    Product Citations

    Aoyagi, R., Ikeda, K., Isobe, Y., et al. Comprehensive analyses of oxidized phospholipids using a measured MS/MS spectra library. J. Lipid. Res. 58(11), 2229-2237 (2017).

    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).