2-[[(E)-octadec-9-enoyl]amino]ethyl dihydrogen phosphate

Base Information

• Chemical Name: 2-[[(E)-octadec-9-enoyl]amino]ethyl dihydrogen phosphate
• CAS No.: 24435-25-4
• Molecular Formula: C₂₀H₄₀NO₅P
• Molecular Weight: 405.515
• ChEMBL ID: CHEMBL1574292
• DSSTox Substance ID: DTXSID00590850
• Wikidata: Q27087826
• Mol file: 24435-25-4.mol

Synonyms:24435-25-4;2-[[(E)-octadec-9-enoyl]amino]ethyl dihydrogen phosphate;N-acyl ethanolamide phosphate;GTPL6982;CHEMBL1574292;SCHEMBL23014613;DTXSID00590850;NAEPA, >=98 (TLC), solid;ZAA43525;NCGC00165839-01;Q27087826;2-{[(9E)-Octadec-9-enoyl]amino}ethyl dihydrogen phosphate

Chemical Property of 2-[[(E)-octadec-9-enoyl]amino]ethyl dihydrogen phosphate

Chemical Property:

• Melting Point: 75.8-84.0 °C
• PSA: 109.16000
• LogP: 6.08970
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 28 mg/mL, soluble
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 19
• Exact Mass: 405.26441037
• Heavy Atom Count: 27
• Complexity: 423

Purity/Quality:

97% ^*data from raw suppliers

NAEPA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)NCCOP(=O)(O)O
• Isomeric SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)NCCOP(=O)(O)O
• Uses: NAEPA is a selective EDG-2 (LPA1) receptor agonist and a LPA mimetic.

Technology Process of 2-[[(E)-octadec-9-enoyl]amino]ethyl dihydrogen phosphate

There total 3 articles about 2-[[(E)-octadec-9-enoyl]amino]ethyl dihydrogen phosphate 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: 50.0%

Phosphoric acid dibenzyl ester 2-((Z)-octadec-9-enoylamino)-ethyl ester (183323-44-6) → NAEPA (24435-25-4)

Guidance literature:

With palladium on activated charcoal; acetic acid; cyclohexene; In tetrahydrofuran; Heating;

DOI:10.1124/mol.52.1.75

Reference yield:

(Z)-9-octadecenoyl chloride (112-77-6) → NAEPA (24435-25-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 20 °C

2.1: tetrazole / CH₂Cl₂ / 1 h

2.2: aq. H₂O₂ / CH₂Cl₂ / 2 h

3.1: 50 percent / cyclohexene; Pd/C; acetic acid / tetrahydrofuran / Heating

With 1H-tetrazole; palladium on activated charcoal; acetic acid; cyclohexene; In tetrahydrofuran; dichloromethane;

DOI:10.1124/mol.52.1.75

Reference yield:

N-oleoylethanolamine (7545-20-2,111-58-0) → NAEPA (24435-25-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrazole / CH₂Cl₂ / 1 h

1.2: aq. H₂O₂ / CH₂Cl₂ / 2 h

2.1: 50 percent / cyclohexene; Pd/C; acetic acid / tetrahydrofuran / Heating

With 1H-tetrazole; palladium on activated charcoal; acetic acid; cyclohexene; In tetrahydrofuran; dichloromethane;

DOI:10.1124/mol.52.1.75

upstream raw materials:

Phosphoric acid dibenzyl ester 2-((Z)-octadec-9-enoylamino)-ethyl ester

(Z)-9-octadecenoyl chloride

N-oleoylethanolamine

Refernces