(17R,18S)-Epoxyeicosatetraenoic acid  (Synonyms: 17(R),18(S)-EETeTr)

(17R,18S)-Epoxyeicosatetraenoic acid (17 (R),18 (S)-EETeTr) is a physiologically active fatty acid metabolite and also a vasodilator targeting BKα. (17R,18S)-Epoxyeicosatetraenoic acid activates the outward potassium current mediated by BK channels, and this effect is independent of the BKβ1 subunit, intracellular/extracellular calcium levels, and sarcoplasmic reticulum calcium release regulated by RyR3. (17R,18S)-Epoxyeicosatetraenoic acid is produced by the epoxidation of eicosapentaenoic acid mediated by CYP1A1 variants. (17R,18S)-Epoxyeicosatetraenoic acid is applicable to research related to arrhythmia^[1][2][3].

(17R,18S)-Epoxyeicosatetraenoic acid (17(R),18(S)-EETeTr) (100 nM; 40 min) stimulates BK channel-mediated outward K⁺ currents by up to 2.6-fold at +60 mV in freshly isolated rat cerebral artery VSMC, independent of intracellular or extracellular Ca²⁺ changes, L-type Ca²⁺ channels, or EET receptors targeted by 14,15-epoxyeicosa-5(Z)-enoic acid^[1].
(17R,18S)-Epoxyeicosatetraenoic acid (100 nmol l⁻¹; 40 min) stimulates BK channel-mediated outward K⁺ currents by up to 3.5-fold at +60 mV in wild-type, BKβ1^(-/-), and RyR3^(-/-) mouse cerebral artery VSMC, but has no effect in BKα^(-/-) mouse cerebral artery VSMC, demonstrating dependence on the BKα subunit^[1].
(17R,18S)-Epoxyeicosatetraenoic acid (1 μmol l⁻¹; 40 min) stimulates BK channel-mediated outward K⁺ currents by 2.2-fold at +100 mV in freshly isolated wild-type mouse mesenteric artery VSMC^[1].
(17R,18S)-Epoxyeicosatetraenoic acid exerts immediate negative chronotropic effects and protects neonatal rat cardiomyocytes against calcium overload with an EC₅₀ of 1-2 nM, and reduces beating rate by -21.3 beats/min when incubated at 30 nM for 5 min^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

318.45

C₂₀H₃₀O₃

725246-18-4

Liquid

Colorless to light yellow

OC(CCC/C=C\C/C=C\C/C=C\C/C=C\C[C@@H]1[C@@H](O1)CC)=O

Room temperature in continental US; may vary elsewhere.

Solution, -20°C, 2 years

• [1]. Hercule HC, et al. The vasodilator 17,18-epoxyeicosatetraenoic acid targets the pore-forming BK alpha channel subunit in rodents. Exp Physiol. 2007;92(6):1067-1076.  [Content Brief]

  [2]. Falck JR, et al. 17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues. J Med Chem. 2011;54(12):4109-4118.  [Content Brief]

  [3]. Schwarz D, et al. Human CYP1A1 variants lead to differential eicosapentaenoic acid metabolite patterns. Biochem Biophys Res Commun. 2005;336(3):779-783.  [Content Brief]