Biologically active oxidative derivative of linoleic acid
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trans-EKODE-(E)-Ib

Item No. 10004224

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-9-oxo-11-((2R,3S)-3-pentyl-2-oxiranyl)-10E-undecenoic acid
CAS Number
478931-82-7
Synonyms
  • 12,13-epoxy-9-keto-10(trans)-Octadecenoic Acid
Molecular Formula
C18H30O4
Formula Weight
310.4
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): .5 mg/ml
λmax
233 nm
SMILES
CCCCC[C@@H](O1)[C@@H]1/C=C/C(CCCCCCCC(O)=O)=O.CCCCC[C@H](O2)[C@H]2/C=C/C(CCCCCCCC(O)=O)=O
InChi Code
InChI=1S/2C18H30O4/c2*1-2-3-7-11-16-17(22-16)14-13-15(19)10-8-5-4-6-9-12-18(20)21/h2*13-14,16-17H,2-12H2,1H3,(H,20,21)/b2*14-13+/t2*16-,17+/m10/s1
InChi Key
OZBYZWCEGJZYHH-GBODHDJKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $54

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    50 µg

    $102

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    100 µg

    $190

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    500 µg

    $834

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    Product Description

    trans-EKODE-(E)-Ib is a biologically active peroxidation product of linoleic acid that is characterized, structurally, by having a trans carbon-carbon double bond between the 9-keto and 12,13-epoxy groups. It activates an antioxidant response element (ARE) in neuronal cells and induces the expression of ARE-regulated cytoprotective genes like NQO1.1 This EKODE also stimulates the synthesis of aldosterone and corticosterone in adrenal cells when supplied at 1-5 μM.2,3 This effect appears to be mediated by a rise in intracellular calcium.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, R., Kern, J.T., Goodfriend, T.L., et al. Activation of the antioxidant response element by specific oxidized metabolites of linoleic acid. Prostaglandins Leukot. Essent. Fatty Acids 81(1), 53-59 (2009).

    2. Goodfriend, T.L., Ball, D.L., Raff, H., et al. Oxidized products of linoleic acid stimulate adrenal steroidogenesis. Endocr. Res. 28(4), 325-330 (2002).

    3. Goodfriend, T.L., Ball, D.L., Egan, B.M., et al. Epoxy-keto derivative of linoleic acid stimulates aldosterone secretion. Hypertension 43[part 2], 358-363 (2004).

    4. Payet, M.D., Goodfriend, T.L., Bilodeau, L., et al. An oxidized metabolite of linoleic acid increases intracellular calcium in rat adrenal glomerulosa cells. Am. J. Physiol. Endocrinol. Metab. 291, E1160-E1167 (2006).