Basic information
- CAS
17364-16-8- Standard SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)([O-])OCC[N+](C)(C)C- InChIKey
ASWBNKHCZGQVJV-HSZRJFAPSA-N- Molecular formula
- C24H50NO7P
- Average molar mass
- 495.6 g/mol
- Monoisotopic mass
- 495.33248993
Overview
1-hexadecanoyl-sn-glycero-3-phosphocholine is a lysophosphatidylcholine 16:0 in which a hexadecanoyl (palmitoyl) group is attached to the glycero moiety at position 1. It has a role as a mouse metabolite. It is a 1-O-acyl-sn-glycero-3-phosphocholine and a lysophosphatidylcholine 16:0.
Names & identifiers
- Preferred name
- 1-Palmitoyl-sn-glycero-3-phosphocholine
- IUPAC
- [(2R)-3-hexadecanoyloxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
- English name
- 1-Palmitoyl-sn-glycero-3-phosphocholine
- Molecular formula
- C24H50NO7P
- Molecular weight
- 495.63
Names & synonyms
1-Palmitoyl-sn-glycero-3-phosphocholine17364-16-8[(2R)-3-hexadecanoyloxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphateJD6PYE3XUXDTXSID30914020((2R)-3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphateRefChem:1056179DTXCID9013430161-hexadecanoyl-sn-glycero-3-phosphocholineLPC(16:0/0:0)LysoPC(16:0)MFCD00036904
Show more names
LYSO-PC1-PALMITOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHOCHOLINELYSO-PPCPalmitoyl Lyso-phosphocholine1-Pal PCP-LYSO-PCCholine Impurity 1LysoFos Choline 16
97281-38-416:0 LYSO-PCCHEBI:72998Lysophosphatidylcholine(16:0/0:0)PC(16:0/0:0)1-16:0-lysoPC16:0 Lyso PC(R)-2-Hydroxy-3-(palmitoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 5.6
- Topological polar surface area
- 105 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 24
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 517
Experimental & physicochemical properties
Lipids
Lipids -> Unambiguous Lipids
Lipids -> Glycerophospholipids [GP] -> Glycerophosphocholines [GP01] -> Monoacylglycerophosphocholines [GP0105]
Physical DescriptionSolid
Collision Cross Section232.9 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Sample Type: Human plasma; Dataset: Unambiguous Lipids]
Physicochemical properties
- Melting point
- 253 °C · 253 °C
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly, Heated)
- form
- Solid
- color
- White to Off-White
- biological source
- synthetic
- optical activity
- Consistent with structure
- BRN
- 5385682 · 5385682
- InChI
- InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1
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
- 10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2923.20.2000
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- 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
Pharmacology
Tissue LocationsAll Tissues
Cellular LocationsExtracellular
Metabolite PathwaysPhospholipid Biosynthesis
Applications
Description1-Palmitoyl-2-hydroxy-sn-glycero-3-PC is the ubiquitous lipid species generated following phospholipase A2 (PLA2) hydrolysis of phosphatidylcholine. It increases the production of reactive oxygen species (ROS) and decreases superoxide dismutase (SOD) and endothelial nitric oxide synthase (eNOS) protein levels and phosphorylation of ERK1/2 in human umbilical vein endothelial cells (HUVECs) when used at a concentration of 125 μM. 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC potentiates the secretion of IL-6, IL-1β, IL-12, and TNF-α in LPS-stimulated M1 macrophages, but has no effect on CD163, CD206, CD36, or IL-10 in LPS-stimulated M2 macrophages when used at concentrations of 0.3 and 1.0 μM. It increases TGF-β1 production and enhances Foxp3 protein levels in Treg cells in isolated human peripheral blood when used at a concentration of 10 μM. 1-Palmitoyl-2-hydroxy-sn-glycero-3-PC enhances neutrophil function, bacterial clearance, and survival in mouse models of sepsis when administered at a dose of 10 mg/kg.
UsesA lipid biomarker for stable and unstable heart disease.
Uses16:0 Lyso PC has been used to reveal the central role of the adipocyte inflammasome in homocysteine-induced insulin resistance. It has also been used for lipid extraction and mass spectrometry analysis.
Suppliers100 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
Related reactions
0 records
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Compound notes
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