1-Octadecanoyl-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-Octadecanoyl-sn-glycero-3-phosphocholine
• CAS No.: 19420-57-6
• Molecular Formula: C26H55NO7P
• Molecular Weight: 523.691
• Hs Code.: 2923900090
• UNII: 2GZO7EJ6ZE
• DSSTox Substance ID: DTXSID101284177
• Wikidata: Q27071327
• Pharos Ligand ID: M3KXJZNJKRPT
• Metabolomics Workbench ID: 14998
• ChEMBL ID: CHEMBL3093101
• Mol file: 19420-57-6.mol

Synonyms:1-octadecyl-glycero-3-phosphocholine;1-stearoyl-2-hydroxy-sn-glycero-3-phosphocholine;1-stearoyl-sn-glycero-3-phosphorylcholine;stearoyl alpha-lysolecithin;stearoyl alpha-lysolecithin, (+-)-isomer;stearoyl alpha-lysolecithin, (R)-isomer;stearoyl L-alpha-lysolecithin;stearoyllysophosphatidylcholine

Chemical Property of 1-Octadecanoyl-sn-glycero-3-phosphocholine

Chemical Property:

• Melting Point: 100-200 °C
• PSA: 114.93000
• LogP: 6.43000
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly, Heated, Sonicated), Water (Slightly, Heated)
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 26
• Exact Mass: 523.36379006
• Heavy Atom Count: 35
• Complexity: 546

Purity/Quality:

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

StearoylL-α-Lysolecithin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Description: Lyso-PC (18:0), also known as 1-stearoyl-sn-glycero-3-phosphocholine, is a lysophosphocoline connceted to hydrophobic fatty acid tail (stearic acid) by a glycerol.
• Uses: 18:0 Lyso PC has been used:to functionalize carbon nanotubes (CNTs) for the development of methods to attach DNA to CNTsto increase the level of lysophosphatidic acid (LPA) in mouseto induce TNF receptor associated factor 3 interacting protein 2 (TRAF3IP2) expression in endothelial cells (EC) Stearoyl L-α-Lysolecithin is an bioactive lysophosphatidylcholine derived compound found to be released by bronchial epithelial cells. Stearoyl L-α-Lysolecithin have also been utilized in the development of liposomes and michelles by drug transdermal delivery devices.

Technology Process of 1-Octadecanoyl-sn-glycero-3-phosphocholine

There total 15 articles about 1-Octadecanoyl-sn-glycero-3-phosphocholine 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: 99.0%

distearoylphosphatidylcholine (816-94-4,18603-43-5) → 1-stearoyl-sn-glycero-3-phosphocholine (19420-57-6,5655-17-4)

Guidance literature:

With tris hydrochloride; sodium docusate; calcium chloride; In 2,2,4-trimethylpentane; at 40 ℃; for 0.5h; pH=8.5; Enzymatic reaction;

DOI:10.1071/CH14606

Reference yield: 97.0%

L-glycero-3-phosphorylcholine (28319-77-9,563-24-6) + Stearoyl chloride (112-76-5) → 1-stearoyl-sn-glycero-3-phosphocholine (19420-57-6,5655-17-4)

Guidance literature:

L-glycero-3-phosphorylcholine; With di(n-butyl)tin oxide; In isopropyl alcohol; for 1h; Heating;

Stearoyl chloride; With TEA; In isopropyl alcohol; at 20 ℃; for 0.583333h; Further stages.;

DOI:10.1039/b604636c

Reference yield: 83.3%

L-glycero-3-phosphorylcholine (28319-77-9,563-24-6) + Stearoyl chloride (112-76-5) → 1-stearoyl-sn-glycero-3-phosphocholine (19420-57-6,5655-17-4)

Guidance literature:

L-glycero-3-phosphorylcholine; Stearoyl chloride; With di(n-butyl)tin oxide; In ethanol; for 0.5h; Reflux;

Stearoyl chloride; With triethylamine; In tetrahydrofuran; at 50 ℃; for 3h;

upstream raw materials:

1-stearoyl-2-benzylglycerophosphocholine

distearoylphosphatidylcholine

L-glycero-3-phosphorylcholine

Stearoyl chloride

Downstream raw materials:

1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine

trimethyl (2-{[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-3-(octadecanoyloxy)propylphosphonato]oxy}ethyl)azanium

(9Z,11E)-(S)-13-(1-Methoxy-1-methyl-ethylperoxy)-octadeca-9,11-dienoic acid (R)-2-[((S)-2,3-dihydroxy-propoxy)-hydroxy-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester; compound with ammonia

(9Z,11E)-(S)-13-Hydroperoxy-octadeca-9,11-dienoic acid (R)-2-[((S)-2,3-dihydroxy-propoxy)-hydroxy-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester; compound with ammonia

Refernces

• 1、 -. "Production method for lysophosphatidyl choline". Paragraph 0014-0016. . Retrieved 2017/08/29.
• 2、 Fasoli, Ezio,Arnone, Alberto,Caligiuri, Antonio,D'Arrigo, Paola,De Ferra, Lorenzo,Servi, Stefano. "Tin-mediated synthesis of lyso-phospholipids". . p. 2974 - 2978. Retrieved 2008/02/11.