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850457P

Avanti

16:0-18:1 PC

Avanti Polar Lipids

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Synonym(s):
1-hexadecanoyl-2--(9Z-octadecenoyl)-sn-glycero-3-phosphocholine; POPC; PC(16:0/18:1(9Z))
Empirical Formula (Hill Notation):
C42H82NO8P
CAS Number:
Molecular Weight:
760.08
NACRES:
NA.25

description

1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 g (850457P-1g)
pkg of 2 × 100 mg (850457P-200mg)
pkg of 5 × 100 mg (850457P-500mg)
pkg of 1 × 25 mg (850457P-25mg)

manufacturer/tradename

Avanti Polar Lipids

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCCCCCCCCCC)=O)=O

InChI

1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1

InChI key

WTJKGGKOPKCXLL-VYOBOKEXSA-N

Related Categories

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.

Application

16:0-18:1 PC has been used in the preparation of liposomes for the muramyl tripeptide encapsulation. It has also been used in the preparation of membrane scaffold protein 1 nanodisc. 16:0-18:1 PC may be used in the synthesis of discoidal reconstituted high-density lipoproteins.

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.

Packaging

5 mL Clear Glass Sealed Ampule (850457P-200mg)
5 mL Clear Glass Sealed Ampule (850457P-25mg)
5 mL Clear Glass Sealed Ampule (850457P-500mg)
60 mL Amber Wide Mouth Screw Cap Glass Bottle (850457P-1g)

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Modified apolipoprotein (apo) AI by artificial sweetener causes severe premature cellular senescence and atherosclerosis with impairment of functional and structural properties of apoA-I in lipid-free and lipid-bound state
Jang W, et al.
Molecules and Cells, 31(5), 461-470 (2011)
Oxidative degradation of the monolayer of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) in low-level ozone
Qiao L, et al.
The Journal of Physical Chemistry B, 119(44), 14188-14199 (2015)
Fluorophore Labeling, Nanodisc Reconstitution and Single-molecule Observation of a G Protein-coupled Receptor
Lamichhane R, et al.
Bio-protocol, 7(12) (2017)
Michael J Hallock et al.
Biochemistry, 57(50), 6897-6905 (2018-11-21)
The plasma membrane of the cell is a complex, tightly regulated, heterogeneous environment shaped by proteins, lipids, and small molecules. Ca2+ ions are important cellular messengers, spatially separated from anionic lipids. After cell injury, disease, or apoptotic events, anionic lipids
Macrophages inhibit human osteosarcoma cell growth after activation with the bacterial cell wall derivative liposomal muramyl tripeptide in combination with interferon-gamma
Pahl JHW, et al.
Journal of Experimental & Clinical Cancer Research, 33(1), 27-27 (2014)

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