Thioetheramide PC

Base Information

• Chemical Name: Thioetheramide PC
• CAS No.: 116457-99-9
• Molecular Formula: C₄₀H₈₃N₂O₅PS
• Molecular Weight: 735.149
• DSSTox Substance ID: DTXSID60437378
• Nikkaji Number: J562.285I
• Wikidata: Q82252868
• Metabolomics Workbench ID: 70790
• Mol file: 116457-99-9.mol

Synonyms:Thioetheramide PC;116457-99-9;2-[[(2S)-2-(hexadecanoylamino)-3-hexadecylsulfanylpropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium;C04873;3,5-Dioxa-9-thia-4-phosphapentacosan-1-aminium, 4-hydroxy-N,N,N-trimethyl-7-[(1-oxohexadecyl)amino]-, inner salt, 4-oxide, (7S)-;CTK8E7838;DTXSID60437378;1-Hexadecylthio-2-hexadecanoylamino-1,2-dideoxy-sn-glycero-3-phosphocholine;SR-01000947058;SR-01000947058-1;O-[[(S)-2-(Hexadecanoylamino)-3-(hexadecylthio)propyl]phosphono]choline;2-[[(2S)-2-(hexadecanoylamino)-3-hexadecylsulfanyl-propoxy]-hydroxy-phosphoryl]oxyethyl-trimethyl-ammonium

Chemical Property of Thioetheramide PC

Chemical Property:

• PSA: 113.57000
• LogP: 14.85480
• Solubility.: Soluble in DMSO;Soluble in dimethyl formamide
• XLogP3: 14.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 39
• Exact Mass: 735.58385696
• Heavy Atom Count: 49
• Complexity: 767

Purity/Quality:

99% ^*data from raw suppliers

Thioetheramide-PC ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCSCC(COP(=O)(O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCCCCCSC[C@H](COP(=O)(O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCCCCCCCC
• Description: Thioetheramide-PC is a structurally modified phospholipid that functions as a competitive, reversible inhibitor of secretory phospholipase A2 (sPLA2). The IC50 value for thioetheramide-PC is 2 μM at a substrate concentration of 0.5 mM. In addition to binding to the catalytic site of sPLA2, thioetheramide-PC also binds to the activator site of this enzyme. The binding of thioetheramide-PC to the activator site is tighter than its binding to the catalytic site. The result of this dual interaction is that at low concentrations thioetheramide-PC may activate phospholipase activity rather than inhibiting it.

Technology Process of Thioetheramide PC

There total 4 articles about Thioetheramide PC 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: 51.0%

{2-[(2-Amino-3-hexadecylsulfanyl-propoxy)-hydroxy-phosphoryloxy]-ethyl}-trimethyl-ammonium (116457-97-7) + n-hexadecanoyl chloride (112-67-4) → C40H83N2O5PS (116457-99-9)

Guidance literature:

With dmap; In chloroform; for 20h; Ambient temperature;

DOI:10.1016/0040-4039(88)80008-X

Reference yield:

1-iodohexadecane (544-77-4) → C40H83N2O5PS (116457-99-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / CH₃ONa / methanol

2: 1.) triethylamine / 1.) in benzene; 2.) in acetonitrile, 65 deg C, 16 h

3: CF₃COOH / CHCl₃ / 1 h / Ambient temperature

4: 51 percent / DMAP / CHCl₃ / 20 h / Ambient temperature

With dmap; sodium methylate; triethylamine; trifluoroacetic acid; In methanol; chloroform;

DOI:10.1016/0040-4039(88)80008-X

Reference yield:

(S)-3-Hexadecylsulfanyl-2-(trityl-amino)-propan-1-ol (116457-95-5) → C40H83N2O5PS (116457-99-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine / 1.) in benzene; 2.) in acetonitrile, 65 deg C, 16 h

2: CF₃COOH / CHCl₃ / 1 h / Ambient temperature

3: 51 percent / DMAP / CHCl₃ / 20 h / Ambient temperature

With dmap; triethylamine; trifluoroacetic acid; In chloroform;

DOI:10.1016/0040-4039(88)80008-X

upstream raw materials:

{2-[(2-Amino-3-hexadecylsulfanyl-propoxy)-hydroxy-phosphoryloxy]-ethyl}-trimethyl-ammonium

n-hexadecanoyl chloride

1-iodohexadecane

(S)-3-Hexadecylsulfanyl-2-(trityl-amino)-propan-1-ol