PC(16:0/20:4(5Z,8Z,11Z,14Z))

Base Information

• Chemical Name: PC(16:0/20:4(5Z,8Z,11Z,14Z))
• CAS No.: 35418-58-7
• Molecular Formula: C44H80NO8P
• Molecular Weight: 782.081661
• DSSTox Substance ID: DTXSID201255137
• Wikidata: Q27105003
• Metabolomics Workbench ID: 13300
• Mol file: 35418-58-7.mol

Synonyms:1-Palmitoyl-2-arachidoyllecithin;PC(16:0/20:4(5Z,8Z,11Z,14Z));Phosphatidylcholine(16:0/20:4);GPCho(16:0/20:4);1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine;PAPC;1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine;GPCho(16:0/5Z,8Z,11Z,14Z-20:4);PC(16:0/20:4);Phosphatidylcholine(16:0/20:4w6);SCHEMBL236438;1-palmitoyl-2-arachidonoyl-GPC;CHEBI:73003;GPCho(16:0/20:4omega6);PC(16:0/20:4omega6);DTXSID201255137;GPCho(16:0/20:4n6);GPCho(16:0/20:4w6);Phosphatidylcholine(16:0/20:4n6);Phosphatidylcholine(16:0/20:4omega6);BP-29915;PC(16:0/20:4n6);PC(16:0/20:4w6);PD085503;GPC(16:0/20:4);1-Palmitoyl-2-arachidonoylphosphatidylcholine;1-palmitoyl-2-arachidonoyl-GPC (16:0/20:4);Q27105003;PC 16:0/24:4(5Z,8Z,11Z,14Z);(2R)-3-(hexadecanoyloxy)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl 2-(trimethylazaniumyl)ethyl phosphate

Chemical Property of PC(16:0/20:4(5Z,8Z,11Z,14Z))

Chemical Property:

• PSA: 121.00000
• LogP: 12.34640
• Storage Temp.: ?20°C
• XLogP3: 12.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 40
• Exact Mass: 781.56215551
• Heavy Atom Count: 54
• Complexity: 1060

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Palmitoyl-2-arachidoyllecithin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 63-20-22-36/38-40-48/20/22-67
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Ambiguous Lipids
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
• Description: 1-Palmitoyl-2-arachidonoyl-sn-glycero-3-PC (PAPC) is a phospholipid containing palmitic acid (16:0) and arachidonic acid (20:4) at the sn-1 and sn-2 positions, respectively, that is found in biological membranes. PAPC is oxidized in vivo, and its oxidation products are involved in chronic inflammation and vascular disease. PAPC has been used to study signaling of oxidized phospholipids. Levels of PAPC are decreased in isolated human multiple myeloma cells.
• Uses: 1-Palmitoyl-2-arachidoyllecithin, is a phospholipid, that can be used for the studies, and elevation of autoantibodies against oxidized palmitoyl arachidonoyl phosphocholine in patients with hypertension and myocardial infarction. 16:0-20:4 PC is suitable for use:in the preparation of auto-oxidised phospholipid for electrospray ionisation mass spectroscopic (ESI-MS) analysisin liposome preparation for the treatment of organoidas antigen in enzyme linked immunosorbent assay (ELISA) for the detection of autoantibodies to phospholipids

Technology Process of PC(16:0/20:4(5Z,8Z,11Z,14Z))

There total 7 articles about PC(16:0/20:4(5Z,8Z,11Z,14Z)) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.5%

2-chloroethyl phosphorodichloridate (1455-05-6) + 1-O-palmitoyl-2-arachidonoyl-glycerol (65886-78-4) + trimethylamine (75-50-3) → 1-palmitoyl-2-arachidonyl-sn-glycero-3-phosphorylcholine (35418-58-7,39735-07-4)

Guidance literature:

2-chloroethyl phosphorodichloridate; 1-O-palmitoyl-2-arachidonoyl-glycerol; With triethylamine; In dichloromethane;

With water; triethylamine; In dichloromethane;

trimethylamine; In ethanol; at 70 - 80 ℃; for 72h;

DOI:10.1248/cpb.47.1659

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 1-palmitoyl-2-arachidonyl-sn-glycero-3-phosphorylcholine (35418-58-7,39735-07-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DMAP; DCC / CH₂Cl₂ / 24 h / 20 °C

2.1: ethanol / 6 h / 20 °C / UV-irradiation

3.1: Et₃N / CH₂Cl₂

3.2: H₂O; Et₃N / CH₂Cl₂

3.3: 63.5 percent / ethanol / 72 h / 70 - 80 °C

With dmap; triethylamine; dicyclohexyl-carbodiimide; In ethanol; dichloromethane; 1.1: Esterification / 2.1: deprotection / 3.1: phosphorylation / 3.2: Hydrolysis / 3.3: Substitution;

DOI:10.1248/cpb.47.1659

Reference yield:

1-hexadecylcarboxylic acid (57-10-3) → 1-palmitoyl-2-arachidonyl-sn-glycero-3-phosphorylcholine (35418-58-7,39735-07-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75.3 percent / DMAP; DCC / CH₂Cl₂ / 0 °C

2.1: DMAP; DCC / CH₂Cl₂ / 24 h / 20 °C

3.1: ethanol / 6 h / 20 °C / UV-irradiation

4.1: Et₃N / CH₂Cl₂

4.2: H₂O; Et₃N / CH₂Cl₂

4.3: 63.5 percent / ethanol / 72 h / 70 - 80 °C

With dmap; triethylamine; dicyclohexyl-carbodiimide; In ethanol; dichloromethane; 1.1: Esterification / 2.1: Esterification / 3.1: deprotection / 4.1: phosphorylation / 4.2: Hydrolysis / 4.3: Substitution;

DOI:10.1248/cpb.47.1659

upstream raw materials:

2-chloroethyl phosphorodichloridate

1-O-palmitoyl-2-arachidonoyl-glycerol

trimethylamine

all cis 5,8,11,14-eicosatetraenoic acid

Downstream raw materials:

1‐palmitoyl‐2‐(5‐oxovaleroyl)‐sn‐glycero‐3‐phosphocholine

Refernces