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Cat. Number
652635194748736
Chemical Name
(±)8,9-DHET-d11
References
Formal Name (±)8,​9-​dihydroxy-​5Z,​11Z,​14Z-​eicosatrienoic-​16,​16,​17,​17,​18,​18,​19,​19,​20,​20,​20-​d11 acid
Molecular Formula C20H33D11O4
Formula Weight 349.6
Formulation A solution in ethanol
Purity ≥99% deuterated product
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES CCCCC/C=CC/C=CCC(O)​C(O)​C/C=CCCCC(=O)​O

Background Reading

Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. J Biol Chem 257 3771-3781 (1982).

Zhang, J.Y., Prakash, C., Yamashita, K., et al. Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase. Biochem Biophys Res Commun 183 138-143 (1992).

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Description

(±)8,9-DiHETrE-d11 contains 11 deuterium atoms at the 16, 16, 17, 17, 18, 18, 19, 19, 20, 20, and 20 positions. It is intended for use as an internal standard for the quantification of (±)8,9-DiHETrE by GC- or LC-mass spectrometry. Epoxide hydrolases convert the EpETrEs into vicinal diols, with the concurrent loss of much of their biological activity.1 The 8(S),9(R)-EpETrE isomer is metabolized by platelet COX to form 8(S),9(R),11(R)-THETA, a trihydroxy fatty acid which may act as a renal vasoconstrictor.2

1 Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. J Biol Chem 257 3771-3781 (1982).

2 Zhang, J.Y., Prakash, C., Yamashita, K., et al. Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase. Biochem Biophys Res Commun 183 138-143 (1992).

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