Epoxide hydrolases convert the EETs into vicinal diols, with the concurrent loss of much of their biological activity. The 8(S),9(R)-EET 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.
Eicosapentaenoic acid is an ω-3 polyunsaturated fatty acid that is abundant in marine organisms and fish oils. EPA is metabolized, in part, through cytochrome P450-catalyzed epoxidation followed by conversion to the vicinal diols by epoxide hydrolases. (±)5(6)-DiHETE is a possible metabolite produced from EPA following epoxidation of the α-5 double bond. The biological activity of (±)5(6)-DiHETE has not been documented.
(±)-11(12)-DiHET is an oxylipin. 11(S),12(S)-DiHET and 11(R),12(R)-DiHET are vicinal diols formedviaenzymatic hydration of 11(12)-EET by cytosolic or soluble epoxide hydrolases in a non-stereoselective manner.1,2,3(±)11(12)-DiHET MaxSpec standard is a quantitative grade standard of (±)11(12)-DiHET that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This (±)11(12)-DiHET MaxSpec standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product.Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
5(6)-DiHET is a racemic compound synthesized through the action of epoxide hydrolases on 5(6)-EET, encompassing both enantiomeric forms. It serves as a quantitative marker for 5(6)-EET, facilitating its measurement by utilizing the compound's conversion to 5(6)-δ-lactone in solution. Additionally, 5(6)-DiHET activates large-conductance calcium-activated potassium (KCa1.1/BK) channels in rat small coronary artery smooth muscle cells, supporting its biological significance in vascular regulation. It also acts as a substrate for sheep seminal vesicle COX, leading to the in vitro production of 5,6-dihydroxy prostaglandin E1 and F1α metabolites. Notably, its levels diminish in the plasma of rats subjected to a high-fat diet, indicating a potential role in the pathophysiology of hyperlipidemia.