Prostaglandin E2 Ethanolamide

Base Information

• Chemical Name: Prostaglandin E2 Ethanolamide
• CAS No.: 194935-38-1
• Molecular Formula: C₂₂H₃₇NO₅
• Molecular Weight: 395.539
• Nikkaji Number: J870.169E
• Wikidata: Q76293798
• Metabolomics Workbench ID: 2493
• ChEMBL ID: CHEMBL3398551
• Mol file: 194935-38-1.mol

Synonyms:dinoprostone ethanolamide;PGE(2) ethanolamide;PGE2 ethanolamide;prostaglandin E(2) ethanolamide;prostaglandin E2 ethanolamide;prostamide E2

Chemical Property of Prostaglandin E2 Ethanolamide

Chemical Property:

• PSA: 106.86000
• LogP: 2.66590
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 395.26717328
• Heavy Atom Count: 28
• Complexity: 517

Purity/Quality:

98%Min ^*data from raw suppliers

ProstaglandinE2Ethanolamide-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)NCCO)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)NCCO)O)O
• Description: Prostaglandin E2 ethanolamide (PGE2-EA) is an analog of PGE2 with improved water solubility and stability. PGE2-EA is formed via COX-2 metabolism of arachidonoyl ethanolamide (AEA; ) and acts as an agonist at E prostanoid (EP) receptors 1-4 (Kis = 2.45, 0.46, 0.2, and 0.51 μM, respectively). It also inhibits indoleamine 2,3-dioxygenase-1 (IDO-1) in THP-1 cells and human monocytes (IC50s = 5.7 and 4.7 μM, respectively). PGE2-EA (10 μM) prevents morphological changes and F-actin rearrangement as well as reduces L-homocysteine-induced NLRP3 inflammasome formation and activation in podocytes. Ex vivo, PGE2-EA reduces luminal damage and lymphocyte infiltration in a human mucosal explant colitis model.
• Uses: Prostaglandin E2 Ethanolamide-d4 is the isotope labelled analogue of Prostaglandin E2 Ethanolamide, an analogue of Prostaglandin E2 (P838610). Prostaglandin E2 is most common and most biologically potent of mammalian prostaglandins.

Technology Process of Prostaglandin E2 Ethanolamide

There total 2 articles about Prostaglandin E2 Ethanolamide 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:

dinoprostone (363-24-6) + ethanolamine (141-43-5) → Prostaglandin E2 ethanolamide (194935-38-1)

Guidance literature:

dinoprostone; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In acetonitrile; at 20 ℃; for 0.25h;

ethanolamine; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1007/s13361-018-2051-6

Reference yield:

prostaglandin H2 1-ethanolamide 9,11-cycloendoperoxide (398138-27-7) → Prostaglandin E2 ethanolamide (194935-38-1)

Guidance literature:

With PGE Synthase;

upstream raw materials:

prostaglandin H₂ 1-ethanolamide 9,11-cycloendoperoxide

dinoprostone

ethanolamine