N-[2-(3,4-Dihydroxyphenyl)ethyl]hexadecanamide

Base Information

• Chemical Name: N-[2-(3,4-Dihydroxyphenyl)ethyl]hexadecanamide
• CAS No.: 136181-87-8
• Molecular Formula: C₂₄H₄₁NO₃
• Molecular Weight: 391.594
• ChEMBL ID: CHEMBL457419
• DSSTox Substance ID: DTXSID90587875
• Metabolomics Workbench ID: 119444
• Nikkaji Number: J1.900.775H
• Wikidata: Q27164120
• Mol file: 136181-87-8.mol

Synonyms:N-palmitoyl dopamine

Chemical Property of N-[2-(3,4-Dihydroxyphenyl)ethyl]hexadecanamide

Chemical Property:

• Vapor Pressure: 1.7E-14mmHg at 25°C
• Refractive Index: 1.514
• Boiling Point: 589.5 °C at 760 mmHg
• Flash Point: 310.3 °C
• PSA: 69.56000
• Density: 1.006 g/cm³
• LogP: 6.62870
• Storage Temp.: Store at +4°C
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 17
• Exact Mass: 391.30864417
• Heavy Atom Count: 28
• Complexity: 375

Purity/Quality:

99% ^*data from raw suppliers

PALDA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NCCC1=CC(=C(C=C1)O)O
• Description: Several different fatty acyl dopamine analogs, such as N-arachidonoyl dopamine (NADA), N-oleoyl dopamine (ODA) and N-palmitoyl dopamine (PALDA), have been isolated and characterized from bovine brain. Structurally, PALDA is the amide of palmitic acid and dopamine and is therefore a “hybrid” analog which incorporates components of both the anandamide-like and dopamine neurotransmitter pathways. Unlike NADA and ODA, PALDA is nearly inactive as a vanilloid receptor 1 (VR1) ligand and fails to elicit hyperalgesic or nocifensive responses in vivo. However, PALDA exhibits an “entourage” effect at concentrations of 0.1-10 μM by potentiating the VR1-mediated effects of NADA and anandamide.
• Uses: PALDA is an endogenous fatty acid dopamide.

Technology Process of N-[2-(3,4-Dihydroxyphenyl)ethyl]hexadecanamide

There total 7 articles about N-[2-(3,4-Dihydroxyphenyl)ethyl]hexadecanamide 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%

N-(3,4-dimethoxy-β-phenylethyl)hexadecanamide (708261-28-3) → N-palmitoyldopamine (136181-87-8)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.3390/md11020274

Reference yield: 52.2%

dopamine hydrochloride (62-31-7) + 1-hexadecylcarboxylic acid (57-10-3) → N-palmitoyldopamine (136181-87-8)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1248/cpb.c16-00162

Reference yield:

dopamine (51-61-6) + 1-hexadecylcarboxylic acid (57-10-3) → N-palmitoyldopamine (136181-87-8)

Guidance literature:

1-hexadecylcarboxylic acid; With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In ethyl acetate; at 20 ℃; for 1h;

dopamine; In ethyl acetate; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2010.12.046

upstream raw materials:

palmitic anhydride

3-hydroxytyramine hydrobromide

1-hexadecylcarboxylic acid

dopamine