434741

ETYA

Inhibits arachidonic acid uptake and the activities of arachidonic acid specific and non-specific acyl-CoA synthetases.

• Synonym(s): ETYA, 5,8,11,14-Eicosatetraynoic Acid
• Empirical Formula (Hill Notation): C₂₀H₂₄O₂
• CAS Number: 1191-85-1
• Molecular Weight: 296.40
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00036967
• Assay: ≥95% (TLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Quality Segment: 100
• assay: ≥95% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: off-white
• solubility: ethanol: 20 mg/mL, DMSO: soluble
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: OC(=O)CCCC#CCC#CCC#CCC#CCCCCC
• InChI: 1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)
• InChI key: MGLDCXPLYOWQRP-UHFFFAOYSA-N

Description

General description

Cell permeable. Inhibits arachidonic acid uptake and the activities of arachidonic acid specific and non-specific acyl-CoA synthetases. Inhibits phospholipase A₂ (PLA₂) and cytochrome P-450. Inhibits cyclooxygenase (ID₅₀ = 8 µM), 5-lipoxygenase (ID₅₀ = 10 µM), 12-lipoxygenase (ID₅₀ = 300 nM), and 15-lipoxygenase (ID₅₀ = 200 nM) in whole cells. Also acts as a potent modulator of Ca²⁺ entry into cells. Blocks monocyte binding in minimally-oxidized LDL in endothelial cells. Stimulates luteinizing hormone release from cultured pituitary cells.

Cell-permeable. Inhibits arachidonic acid uptake and arachidonic acid specific and nonspecific acyl-CoA synthesis. Inhibits phospholipase A₂ (PLA₂) and cytochrome P-450. Inhibits cyclooxygenase (ID₅₀ = 8 µM), 5-lipoxygenase (ID₅₀ = 10 µM), 12-lipoxygenase (ID₅₀ = 300 nM), and 15-lipoxygenase (ID₅₀ = 200 nM) in whole cells. A potent modulator of Ca²⁺ entry into cells. Stimulates luteinizing hormone release from cultured pituitary cells.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
PLA₂

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 8 µM, 10 µM, 300 nM, 200 nM against cyclooxygenase, 5-lipoxygenase, 12-lipoxygenase, and 15-lipoxygenase , respectively, in whole cells

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Honda, H.M., et al. 1999. Arterioscler. Thromb. Vasc. Biol.19, 680.
Ekokoski, E., and Tornquist, K. 1994. Biochim. Biophys. Acta 1223, 274.
Ondrey, F., et al. 1989. Cancer Res.49, 1138.
Kuhn, H., et al. 1984. Eur. J. Biochem.139, 577.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable