ChemicalBook CAS DataBase List 26853-31-6

26853-31-6

Name	1-PALMITOYL-2-OLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
CAS	26853-31-6
EINECS(EC#)	248-056-7
Molecular Formula	C42H82NO8P
MDL Number	MFCD00043212
Molecular Weight	760.08
MOL File	26853-31-6.mol

Chemical Properties

Melting point	-3 °C
storage temp.	-20°C
solubility	Ethanol: 25mg/ml
form	A crystalline solid
color	White to off-white
biological source	synthetic
BRN	4173237
InChIKey	WTJKGGKOPKCXLL-ULLJZQASNA-N
SMILES	[C@@H](OC(=O)CCCCCCC/C=C/CCCCCCCC)(COC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C \|&1:0,r\|

Safety Data

Symbol(GHS)	GHS06,GHS08
Signal word	Danger
Hazard statements	H302-H315-H319-H331-H336-H351-H361d-H372-H412
Precautionary statements	P201-P273-P301+P312+P330-P302+P352-P304+P340+P311-P308+P313
Safety Statements	22-24/25 less more
WGK Germany	3
F	1-8-10
Storage Class	11 - Combustible Solids

Hazard Information

Description

1-Palmitoyl-2-oleoyl-sn-glycero-3-PC (POPC) is a phospholipid containing 16:0 and 18:1 fatty acids at the sn-1 and sn-2 positions, respectively. It belongs to a class of phospholipids that are a major component of biological membranes. This compound can be used for liposome production in order to study the properties of lipid bilayers.

Uses

Glycerophospholipids act as regulators of various enzyme activities, and can be used as biological markers to indicate pathological states.

Application

POPC is an important phospholipid for biophysical experiments and has been used to study various subjects such as lipid rafts. POPC is also used in systems mimicking the cell membrane such as Nanodiscs. It is available commercially synthetically and is naturally present in eukaryotic cell membranes.

Definition

ChEBI: 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine is a phosphatidylcholine 34:1 in which the 1- and 2-acyl groups are specified as hexadecanoyl (palmitoyl) and 9Z-octadecenoyl (oleoyl) respectively. It has a role as a mouse metabolite. It is a phosphatidylcholine 34:1 and a 1-acyl-2-oleoyl-sn-glycero-3-phosphocholine betaine. It is functionally related to a hexadecanoic acid and an oleic acid.

General Description

POPC is typically considered one of the model lipids for biophysical experiments. The fatty acid composition, i.e., saturated chain in the sn-1 position and unsaturated chain in the sn-2 position, mimics mammalian phospholipid composition. Since the major constituent in Egg PC is 1-palmitoyl-2-oleoyl PC, POPC is an excellent synthetic substitute for EPC.

Biochem/physiol Actions

1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC)or 16:0-18:1 PC plays an important role as a lung surfactant and reduces surface tension. POPC mimics natural cell membrane and may be useful for unsaturated lipids oxidation studies. Its interaction with ozone leads to oxidative decomposition at the oleoyl strand C-C moiety.

References

[1] MARIA JO?O MORENO Winchil L C V Luís M B B Estronca. Translocation of phospholipids and dithionite permeability in liquid-ordered and liquid-disordered membranes.[J]. Biophysical journal, 2006, 91 3: 873-881. DOI: 10.1529/biophysj.106.082115

Spectrum Detail

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