Docosahexaenoyl Ethanolamide

Base Information

• Chemical Name: Docosahexaenoyl Ethanolamide
• CAS No.: 162758-94-3
• Molecular Formula: C24H37 N O2
• Molecular Weight: 371.563
• DSSTox Substance ID: DTXSID50678596
• Wikidata: Q27158436
• Metabolomics Workbench ID: 4656
• ChEMBL ID: CHEMBL1482206
• Mol file: 162758-94-3.mol

Synonyms:N-docosahexaenoylethanolamine;synaptamide

Chemical Property of Docosahexaenoyl Ethanolamide

Chemical Property:

• PSA: 49.33000
• LogP: 5.96370
• Storage Temp.: ?20°C
• Solubility.: Soluble in DMSO (up to 35 mg/ml)
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 371.282429423
• Heavy Atom Count: 27
• Complexity: 511

Purity/Quality:

98%Min ^*data from raw suppliers

Docosahexaenoyl ethanolamide ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)NCCO
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCO
• Description: Synaptamide (162758-94-3) is an anandamide-like lipid mediator produced from DHA in the brain. Stimulates neurite growth, synaptogenesis and glutamatergic synaptic activity in developing hippocampal neurons at 10-100 nM.1?Potently induces neuronal differentiation of neural stem cells.2?Promotes growth of cortical axons via modulation of hedgehog signaling.3?Binds to and activates orphan receptor GPR110, stimulating cAMP production at low nM concentrations.4?Reduces LPS-induced TNFα production in cultured microglia cells and ameliorates LPS-induced neuroinflammation in a mouse model.5

Technology Process of Docosahexaenoyl Ethanolamide

There total 1 articles about Docosahexaenoyl 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: 75.0%

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate (81926-94-5,84494-72-4) + ethanolamine (141-43-5) → docosahexaenoic acid (6217-54-5) + N-docosahexaenoylethanolamine (162758-94-3)

Guidance literature:

With Novozym 435 lipase on resin; In acetone; at 35 ℃; for 8h; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.bmcl.2014.10.084

Reference yield:

N-docosahexaenoylethanolamine (162758-94-3) → C24H37NO3 + C24H37NO3

Guidance literature:

With tert.-butylhydroperoxide; peroxygenase from oat flour; In aq. phosphate buffer; acetone; at 25 ℃; for 4h; pH=7.4; Reagent/catalyst; Solvent; Concentration; Overall yield = 44 mg; stereoselective reaction; Catalytic behavior; Enzymatic reaction;

DOI:10.1016/j.bioorg.2021.105014

upstream raw materials:

all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate

ethanolamine

Refernces