850165P

18:0-20:4 PI(4,5)P2

1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1′-myo-inositol-4′,5′-bisphosphate) (ammonium salt), powder

• Synonym(s): 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-[phosphoinositol-4,5-bisphosphate] (ammonium salt); PIP2[4′,5′](18:0/20:4(5Z,8Z,11Z,14Z))
• Empirical Formula (Hill Notation): C₄₇H₉₄N₃O₁₉P₃
• CAS Number: 799268-59-0
• Molecular Weight: 1098.18
• UNSPSC Code: 51191904
• NACRES: NA.25

Properties

• Assay: >99% (TLC)
• form: powder
• packaging: pkg of 1 × 100 μg (with stopper and crimp cap (850165P-100ug)); pkg of 1 × 500 μg (with stopper and crimp cap (850165P-500ug))
• manufacturer/tradename: Avanti Research^™ - A Croda Brand 850165P
• lipid type: cardiolipins; phospholipids
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: [H][C@@](COP([O-])(O[C@H]1[C@H](O)[C@@H](OP(O)([O-])=O)[C@H](OP([O-])(O)=O)[C@@H](O)[C@H]1O)=O)(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O.[NH4+].[NH4+].[NH4+]
• InChI key: GAIOWTITBYPFJE-WGJQOQIESA-N

Description

General description

Although PI(4,5)P2 is a minor component of cell membranes, it plays a critical role as a substrate for a number of important signaling proteins. PI(4,5)P2 is an intermediate in the IP3/DAG pathway where it is hydrolyzed by phospholipase C to liberate the second messengers, inositol 1,4,5-triphosphate (IP3) and diacylglycerol (DAG). PI(4,5)P2 is also a substrate for PI 3-kinase where it is phosphorylated to PI(3,4,5)P3, an activator of downstream signaling components such as the protein kinase AKT.

Phosphatidylinositol 4,5-bisphosphate (PIP2) is a negatively charged phospholipid, abundant in the plasma membrane.

Application

18:0-20:4 PI(4,5)P2 or 1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1′-myo-inositol-4′,5′-bisphosphate) (ammonium salt) has been used:

• in cryo-electron microscopy (cryo-EM) grid preparation
• in host 1-O-1-(Z)-octadecenyl-2-arachidonoyl-sn-glycero-3-phosphocholine (plasmenyl-SAPC) small unilamellar vesicles (SUVs) in the presence of H₂O₂ to activate cyt c plasmalogenase activity
• to study whether acyl chain types affect phosphatidylinositol 4,5-bisphosphate (PIP2) cluster formation

Packaging

2 mL Amber Serum Vial with Stopper and Crimp Cap (850165P-100ug)

2 mL Amber Serum Vial with Stopper and Crimp Cap (850165P-500ug)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Storage Class Code: 11 - Combustible Solids