1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine
Basic information
- CAS
26853-31-6- Standard SMILES
CCCCCCCCC=CCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C- InChIKey
WTJKGGKOPKCXLL-UHFFFAOYSA-N- Molecular formula
- C42H82NO8P
- Average molar mass
- 760.1 g/mol
- Monoisotopic mass
- 759.57780557
Overview
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine has been reported in Streptomyces roseicoloratus with data available.
Names & identifiers
- Preferred name
- 1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine
- IUPAC
- (3-hexadecanoyloxy-2-octadec-9-enoyloxypropyl) 2-(trimethylazaniumyl)ethyl phosphate
- English name
- POPC
- Molecular formula
- C42H82NO8P
- Molecular weight
- 760.08
Names & synonyms
26853-31-61-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholineC42H82NO8P70778-75-5POPC;1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholineL-b-Oleoyl-g-palmitoyl-a-lecithinPOPC (1 Palmitoyl-U-13C16)2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine2692624-41-0AKOS030242201FP26731
Show more names
1-Palmitoyl-2-oleoyl-sn-glycero-3-PCL-BETA-OLEOYL-GAMMA-PALMITOYL-ALPHA-LECITHIN1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholinePOPC3-sn-Phospha16:0-18:1 PCPOPC (short route)2-oleoyl-1-palmitoyl
[R-(Z)]-4-Hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-3,5,8-trioxa-4-phosphahexacos-17-en-1-aminium 4-Oxide(3-hexadecanoyloxy-2-octadec-9-enoyloxy-propyl) 2-(trimethylammonio)ethyl phosphate
Database identifiers
Properties
Computed structural properties
- XLogP
- 13.6
- Topological polar surface area
- 111 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 41
- Heavy atoms
- 52
- Formal charge
- 0
- Complexity
- 899
Physicochemical properties
- Melting point
- -3 °C · -3 °C
- storage temp.
- -20 °C · -20°C
- solubility
- 25 mg/ml · Ethanol: 25mg/ml
- form
- A crystalline solid
- color
- White to off-white
- biological source
- synthetic
- BRN
- 4173237 · 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|
- FDA UNII
- 895536 Y5 · TE895536Y5
- UNSPSC Code
- 51191904 · 51191904
- NACRES
- 85 · NA.85
- Symbol(GHS)
- 6 · GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H315-H319-H331-H336-H351-H361d-H372-H412
- Precautionary statements
- 201 · P201-P273-P301+P312+P330-P302+P352-P304+P340+P311-P308+P313
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 1-8-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- 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
Chemistry & industry
Applications
Description1-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.
Description1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPhtCho), is a phosphatidylcholine, that belongs to a class of phospholipids that are a major component of biological membranes. This compound has been shown to decrease the expression of α-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptor subunit GluR1 on the plasma membrane of CA1 region of rat hippocampal slices.
UsesThe effect of non-ionic detergent on liposomes was studied with giant POPC liposomes. Increasing concentrations of detergent cause tubular protrusions, then indentations, to develop on spherical liposomes. At higher detergent concentrations, the liposomes burst.
UsesGlycerophospholipids act as regulators of various enzyme activities, and can be used as biological markers to indicate pathological states.
Uses16:0-18:1 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.
General DescriptionPOPC 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.
Additional notes
DefinitionChEBI: 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.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…