CAS 81246-85-7

8,9-Epoxyeicosatrienoic acid

Description:

8,9-Epoxyeicosatrienoic acid (8,9-EET) is a bioactive lipid derived from arachidonic acid, characterized by its epoxide functional group. It is part of the eicosanoid family, which plays crucial roles in various physiological processes, including inflammation, vascular function, and cell signaling. The structure of 8,9-EET features a 20-carbon chain with three double bonds and an epoxide group at the 8 and 9 positions, contributing to its reactivity and biological activity. This compound is known to exhibit vasodilatory effects, influencing blood flow and pressure, and has been implicated in neuroprotective mechanisms. Additionally, 8,9-EET can modulate ion channel activity and has been studied for its potential therapeutic applications in cardiovascular and neurological disorders. Its synthesis occurs through the action of cytochrome P450 enzymes, which convert arachidonic acid into various epoxyeicosatrienoic acids, including 8,9-EET. Overall, this compound is significant in the context of lipid signaling and has garnered interest for its potential roles in health and disease.

Formula: C₂₀H₃₂O₃

InChI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)

InChI key: InChIKey=DBWQSCSXHFNTMO-UHFFFAOYSA-N

SMILES: C(C=CCC=CCCCCC)C1C(CC=CCCCC(O)=O)O1

Synonyms:

• (5E)-7-{3-[(2E,5E)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoic acid
• (5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoic acid
• 5-Heptenoic acid, 7-(3-(2,5-undecadienyl)oxiranyl)-
• 5-Heptenoic acid, 7-[3-(2,5-undecadien-1-yl)-2-oxiranyl]-
• 7-[3-(2,5-Undecadien-1-yl)-2-oxiranyl]-5-heptenoic acid
• 7-[3-(2,5-Undecadienyl)oxiranyl]-5-heptenoic acid
• 8,9-Eet
• 8,9-Epoxyeicosa-5,11,14-trienoic acid
• 8,9-Epoxyeicosatrienoic acid

(+/-)-8,9-Epoxyeicosa-5Z,11Z,14Z-trienoic Acid

Controlled Product

CAS: 81246-85-7

Formula: C₂₀H₃₂O₃

Color and Shape: Neat

Molecular weight: 320.466

Ref: TR-E589143

8,9-Epoxyeicosatrienoic acid

CAS: 81246-85-7

8,9-Epoxyeicosatrienoic acid offers unique protective effects on the glomerulus. It inhibits the increase in glomerular albumin permeability caused by circulating permeability factors (FSPF). Additionally, 8,9-Epoxyeicosatrienoic acid is used in research related to glomerular dysfunction.

Formula: C₂₀H₃₂O₃

Color and Shape: Solid

Molecular weight: 320.47

Ref: TM-T201741