1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine

Base Information

• Chemical Name: 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine
• CAS No.: 27098-24-4
• Molecular Formula: C44H84 N O8 P
• Molecular Weight: 786.127
• DSSTox Substance ID: DTXSID001230503
• Wikidata: Q27105102
• Metabolomics Workbench ID: 13478
• Mol file: 27098-24-4.mol

Synonyms:1-stearoyl-(2-linoleoyl)-sn-glycero-3-phosphocholine;1-stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine;1-stearoyl-2-linoleoylphosphatidylcholine;SLPC;SLPTC

Chemical Property of 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 121.00000
• Density: g/cm³
• LogP: 12.79440
• Storage Temp.: -20°C
• XLogP3: 14
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 42
• Exact Mass: 785.59345564
• Heavy Atom Count: 54
• Complexity: 972

Purity/Quality:

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

1-STEAROYL-2-LINOLEOYL-SN-GLYCERO-3-PHOSPHORYLCHOLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Ambiguous Lipids
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C\C/C=C\CCCCC
• Uses: 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine s used in the preparation of a fiber with resistance to respiratory viral disease. The fiber has exogenous pulmonary surfactant which can enter the body through breathing and play an antiviral role. 18:0-18:2 PC is suitable for use:in the preparation of large unilamellar vesiclesin the preparation of liposomesto prepare oxidised phospholipid by 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH) for multiple reaction monitoring (MRM) analysis

Technology Process of 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine

There total 6 articles about 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine 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: 80.0%

1-0-triphenylmethyl-sn-glycero-3-phosphocholine + 2-linoleoyl-sn-glycero-3-phosphocholine + stearic anhydride (638-08-4) → trimethyl (2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propylphosphonato]oxy}ethyl)azanium (27098-24-4,70106-57-9,923-59-1)

Guidance literature:

Reference yield: 77.0%

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + 1-stearoyl-sn-glycero-3-phosphocholine (19420-57-6,5655-17-4) → trimethyl (2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propylphosphonato]oxy}ethyl)azanium (27098-24-4,70106-57-9,923-59-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In chloroform; at 20 ℃; for 120h;

DOI:10.1111/febs.14807

Reference yield:

vinyl stearate (111-63-7,9003-95-6) → trimethyl (2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propylphosphonato]oxy}ethyl)azanium (27098-24-4,70106-57-9,923-59-1)

Guidance literature:

Multi-step reaction with 3 steps

1: lipase / propan-2-ol

2: 1.) POCl₃, 3.) H₂O, 4.) H₂ / 4.) Pd(OH)2/C / 1.) Et₃N, 2.) pyridine, 4.) H₂O, Ch₃OH

3: DCC, DMAP / CHCl₃

With dmap; water; hydrogen; dicyclohexyl-carbodiimide; lipase; trichlorophosphate; palladium dihydroxide; In chloroform; isopropyl alcohol;

DOI:10.1271/bbb.60.1916

upstream raw materials:

1-stearoyl-2-linoleoyl-sn-glycerol

choline chloride

linoleic acid

1-stearoyl-2-benzylglycerophosphocholine

Downstream raw materials:

distearoylphosphatidylcholine

Refernces

• 1、 Firsov, Alexander M.,Fomich, Maksim A.,Bekish, Andrei V.,Sharko, Olga L.,Kotova, Elena A.,Saal, Harry J.,Vidovic, Dragoslav,Shmanai, Vadim V.,Pratt, Derek A.,Antonenko, Yuri N.,Shchepinov, Mikhail S.. "Threshold protective effect of deuterated polyunsaturated fatty acids on peroxidation of lipid bilayers". . p. 2099 - 2117. Retrieved 2019/03/27.
• 2、 -. "Derivatives of glycerophosphocholine and glycerophosphoethanolamine, their preparation and their use". . . Retrieved 2008/06/13.