87173-80-6
Chemical Structure
5,6-Epoxyeicosatrienoic acid
Synonym(s): 5,6-EET; (±)5,6-EpETrE
- CAS No.: 87173-80-6
- Formula:C20H32O3
- Molecular Weight:320.47
IUPAC Name: 4-((2S,3R)-3-((2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl)oxiran-2-yl)butanoic acid
InChIKey: VBQNSZQZRAGRIX-GSKBNKFLSA-N
SMILES: OC(CCC[C@H]1[C@H](O1)C/C=C\C/C=C\C/C=C\CCCCC)=O
Biological Activity: 5,6-Epoxyeicosatrienoic acid (5,6-EET; (±)5,6-EpETrE) is a fully racemic version of the enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes. In solution, 5,6-Epoxyeicosatrienoic acid degrades into 5,6-DiHET and 5,6-δ-lactone, which can be converted to 5,6-DiHET and quantified by GC-MS. In neuroendocrine cells, such as the anterior pituitary and pancreatic islets, 5,6-Epoxyeicosatrienoic acid has been implicated in the mobilization of calcium and hormone secretion. 5,6-Epoxyeicosatrienoic acid is an inhibitor of T-type voltage-gated calcium channels (Cav3) that inhibits isoforms Cav3.1, Cav3.2 (IC50=0.54 μM), and Cav3. and decreases nifedipine-resistant phenylephrine-induced vasoconstriction in isolated mouse mesenteric arteries via Cav3.2 blockade when used at a concentration of 3 μM. In addition, it is a substrate of COX-1 and COX-2.
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5,6-Epoxyeicosatrienoic acid | 99.07% | 5,6-Epoxyeicosatrienoic acid (5,6-EET; (±)5,6-EpETrE) is a fully racemic version of the enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes. In solution, 5,6-Epoxyeicosatrienoic acid degrades into 5,6-DiHET and 5,6-δ-lactone, which can be converted to 5,6-DiHET and quantified by GC-MS. In neuroendocrine cells, such as the anterior pituitary and pancreatic islets, 5,6-Epoxyeicosatrienoic acid has been implicated in the mobilization of calcium and hormone secretion. 5,6-Epoxyeicosatrienoic acid is an inhibitor of T-type voltage-gated calcium channels (Cav3) that inhibits isoforms Cav3.1, Cav3.2 (IC50=0.54 μM), and Cav3. and decreases nifedipine-resistant phenylephrine-induced vasoconstriction in isolated mouse mesenteric arteries via Cav3.2 blockade when used at a concentration of 3 μM. In addition, it is a substrate of COX-1 and COX-2. | ||||||||||||||||||||
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5,6-Epoxyeicosatrienoic acid-d11 | 5,6-Epoxyeicosatrienoic acid-d11 (5,6-EET-d11) is deuterium labeled 5,6-Epoxyeicosatrienoic acid. 5,6-Epoxyeicosatrienoic acid is one of the four major epoxyeicosatrienoic acid (EET) isomers metabolized from Arachidonic acid (HY-109590). 5,6-Epoxyeicosatrienoic acid induces peripheral vasodilation and lowers blood pressure by inhibiting T-type calcium channels (Cav3.2: IC50 = 0.54 μM). 5,6-Epoxyeicosatrienoic acid causes vasoconstriction in hypoxic pulmonary blood vessels via activating Rho kinase in a membrane depolarization-dependent manner. 5,6-Epoxyeicosatrienoic acid induces mechanical pain by activating TRPA1. 5,6-Epoxyeicosatrienoic acid can be used in studies related to hypoxic pulmonary vasoconstriction, mechanical hyperalgesia and hypertension. | |||||||||||||||||||||
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