181198

Arachidonic Acid

Precursor for prostaglandins, prostacyclin, and thromboxane.

• Synonym(s): Arachidonic Acid, cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic Acid, 20:4
• Empirical Formula (Hill Notation): C₂₀H₃₂O₂
• CAS Number: 506-32-1
• Molecular Weight: 304.47
• MDL number: MFCD00004417

Properties

• Quality Level: 100
• Assay: ≥99% (TLC and GC)
• form: oil
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: colorless
• solubility: ethanol: 5 mg/mL
• shipped in: dry ice
• storage temp.: −70°C
• InChI: 1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6+,10-9+,13-12+,16-15+
• InChI key: YZXBAPSDXZZRGB-CGRWFSSPSA-N

Description

General description

A cis-polyunsaturated fatty acid found in the plasma membrane. Major component of membrane phospholipids. Following its release by cellular phospholipases, it is enzymatically converted to a variety of inflammatory and vasoactive metabolites, such as prostaglandins (via the cyclooxygenase pathway), leukotrienes (via the lipoxygenase pathway), and epoxides (via the cytochrome P450 pathway). Binds to G-protein α-subunits in a covalent, posttranslational manner. Inhibits Ras-GAP. Stimulates the synthesis of nitric oxide by platelets.

Precursor for prostaglandins, prostacyclin, and thromboxane. Binds to G-protein α-subunits in a covalent, post-translational manner. Inhibits Ras-GAP. Stimulates the synthesis of nitric oxide by platelets. Modulates nitric oxide production by prostaglandin synthesis via the cyclooxygenase pathway.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Ras-GAP

Product does not compete with ATP.

Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Harmful (C)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Hallak, H., et al. 1994. J. Biol. Chem. 269, 4713.
Khurana, G., and Bennett, M.R. 1993. Br. J. Pharmacol. 109, 480.
Han, J.-W., et al. 1991. Science252, 576.
Radomski, M.W., et al. 1990. Br. J. Pharmacol. 101, 325.
Neddleman P., et al. 1986. Annu. Rev. Biochem.55, 69.

Legal Information

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

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 235.4 °F - closed cup
• Flash Point(C): 113 °C - closed cup