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trans-EKODE-(E)-Ib Exclusive
Cayman Chemical Item Number 10004224
Description
During oxidative stress, the abundant unsaturated fatty acid linoleic acid undergoes lipid peroxidation to produce α,β-unsaturated epoxy-keto-octadecenoic acids (EKODEs). Nonenzymatic autooxidation of linoleic acid generates six major EKODE isomers, which differ from one another in the positioning and the orientation of the epoxy group relative to the keto moiety.1↗ 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 NQO1.2↗ This EKODE also stimulates the synthesis of aldosterone and corticosterone in adrenal cells when supplied at 1-5 μM.3↗,4↗ This effect appears to be mediated by a rise in intracellular calcium.5↗
1 Lin, D., Zhang, J., and Sayre, L.M. Synthesis of six epoxyketooctadecenoic acid (EKODE) isomers, their generation from nonenzymatic oxidation of linoleic acid, and their reactivity with imidazole nucleophiles. J Org Chem 72 9471-9480 (2007).
2 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 53-59 (2009).
3 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).
4 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).
5 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).
Synonyms 12,13-epoxy-9-keto-10(trans)-Octadecenoic Acid
Formal Name 9-oxo-11-(3-pentyl-2-oxiranyl)-10E-undecenoic acid
CAS Number 478931-82-7
Molecular Formula C18H30O4
Formula Weight 310.2
Formulation A solution in ethanol
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES Copy CCCCCC(O1)C1/C=C/C(CCCCCCCC(O)=O)=O
InCHI Code Copy 1S/C18H30O4/c1-2-3-7-11-16-17(22-16)14-13-15(19)10-8-5-4-6-9-12-18(20)21/h13-14,16-17H,2-12H2,1H3,(H,20,21)/b14-13+
InCHI Key Copy RCMABBHQYMBYKV-BUHFOSPRSA-N |