1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
• CAS No.: 19420-56-5
• Molecular Formula: C26H52 N O7 P
• Molecular Weight: 521.675
• Hs Code.: 2923900090
• UNII: FS74G26ZZ4
• ChEMBL ID: CHEMBL3093102
• DSSTox Substance ID: DTXSID201334331
• Metabolomics Workbench ID: 15001
• Pharos Ligand ID: M3J3785PDJH4
• Wikidata: Q27088173
• Mol file: 19420-56-5.mol

Synonyms:1-(cis-9-octadecenoyl)-sn-glycero-3-phosphocholine;1-OGPC;1-oleoyl lysophosphatidylcholine;1-oleoyl-lysoPC;1-oleoylglycerophosphocholine

Chemical Property of 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

Chemical Property:

• PSA: 114.93000
• LogP: 6.20600
• Storage Temp.: −20°C
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 25
• Exact Mass: 521.34814000
• Heavy Atom Count: 35
• Complexity: 585

Purity/Quality:

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

1-Oleoyl-sn-glycero-3-phosphocholine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)([O-])OCC[N+](C)(C)C)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O
• Uses: 1-Oleoyl-sn-glycero-3-phosphocholine is a marker contained in biological sample for determination of obesity and screening method. 1-Oleoyl-sn-glycero-3-phosphocholine may be used as a reference for the analysis of lysolecithins extracted from tissues and cell membranes. 18:1 Lyso PC is suitable for use as a lysophospholipid?mediator to compare the effect of sphingosylphosphorylcholine (SPC). It has been used as a supplement in Yeast nitrogen base (YNB) medium to rescue choline auxotrophy.

Technology Process of 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

There total 12 articles about 1-(9Z-octadecenoyl)-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: 97.0%

(Z)-9-octadecenoyl chloride (112-77-6) + L-glycero-3-phosphorylcholine (28319-77-9,563-24-6) → 1-oleoyl-L-lysophosphatidylcholine (19420-56-5)

Guidance literature:

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

(Z)-9-octadecenoyl chloride; With TEA; In isopropyl alcohol; at 20 ℃; for 0.583333h; Further stages.;

DOI:10.1039/b604636c

Reference yield:

2-oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine (6753-55-5,26662-91-9,26662-92-0,26853-31-6,67738-47-0,109958-90-9) + propranolol (525-66-6) → O-oleoyl propranolol + O-palmitoyl propranolol + N-palmitoyl propranolol + N-oleoyl propranolol + 1-palmitoyl-sn-glycero-3-phosphocholine (17364-16-8,17364-17-9,17364-18-0,14863-27-5) + 1-oleoyl-L-lysophosphatidylcholine (19420-56-5) + 2-(octadec-cis-9-enoyl)-sn-glycero-3-phosphocholine (22248-65-3) + 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine

Guidance literature:

In aq. buffer; at 37 ℃; for 48h; pH=7.4;

DOI:10.1039/c8sc04831b

Reference yield:

(Z)-9-octadecenoyl chloride (112-77-6) → 1-oleoyl-L-lysophosphatidylcholine (19420-56-5)

Guidance literature:

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

(Z)-9-octadecenoyl chloride; With triethylamine; In isopropyl alcohol; at 0 ℃; for 0.25h;

upstream raw materials:

(Z)-9-octadecenoyl chloride

L-glycero-3-phosphorylcholine

1,2-dipalmitoleoyl-sn-glycero-3-phosphatidylcholine

dioleoylphosphatidylcholine

Downstream raw materials:

1-O-oleoyl-2-O-[12-[N-4-(azido-2,3,5,6-tetrafluorobenzoyl)]aminododecanoyl]-sn-glycero-3-phosphocholine

cis-Octadecenoic acid