CAS 213382-49-1

5,6-Dihydroxyeicosatrienoic acid

Description:

5,6-Dihydroxyeicosatrienoic acid (DHETrE) is a bioactive lipid belonging to the eicosanoid family, which are derived from arachidonic acid. This compound is characterized by the presence of two hydroxyl groups at the 5 and 6 positions of its eicosatrienoic acid backbone, contributing to its unique biochemical properties. DHETrE is known to play a role in various physiological processes, including inflammation and vascular function. It is involved in signaling pathways that can influence cell proliferation, apoptosis, and immune responses. The compound is typically studied in the context of cardiovascular health and metabolic disorders, as it may have implications in the regulation of blood pressure and lipid metabolism. Its synthesis and metabolism are of interest in pharmacological research, particularly for developing therapeutic agents targeting inflammatory diseases. As with many eicosanoids, the biological activity of DHETrE is highly dependent on its concentration and the specific cellular context in which it acts.

Formula: C₂₀H₃₄O₄

InChI: InChI=1/C20H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19(22)16-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-

InChI key: InChIKey=GFNYAPAJUNPMGH-QNEBEIHSNA-N

SMILES: C(C(C/C=C\C/C=C\C/C=C\CCCCC)O)(CCCC(O)=O)O

Synonyms:

• (+/-)5,6-DiHETrE
• (8Z,11Z,14Z)-5,6-Dihydroxy-8,11,14-eicosatrienoic acid
• (±)-5,6-Dihydroxy-8Z,11Z,14Z-eicosatrienoic acid
• 213382-49-1
• 5,6-Dhet
• 5,6-Dihydroxyeicosatrienoic acid
• 8,11,14-Eicosatrienoic acid, 5,6-dihydroxy-, (8Z,11Z,14Z)-

5,6-dihydroxy-8(Z),11(Z),14(Z)-eicosatrienoic acid

CAS: 213382-49-1

Formula: C20H34O4

Purity: >95%

Color and Shape: In solution, Ethanol

Molecular weight: 338.48

Ref: 48-14-3031

(±)​-5,​6-DHET

Controlled Product

CAS: 213382-49-1

Formula: C₂₀H₃₄O₄

Color and Shape: Neat

Molecular weight: 338.482

Ref: TR-D679055

(±)5(6)-DiHET

CAS: 213382-49-1

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.

Formula: C₂₀H₃₄O₄

Color and Shape: Solid

Molecular weight: 338.5

Ref: TM-T84609