Arachidonamide

Base Information

• Chemical Name: Arachidonamide
• CAS No.: 85146-53-8
• Molecular Formula: C₂₀H₃₃NO
• Molecular Weight: 303.488
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID001347885
• Wikidata: Q76294087
• Metabolomics Workbench ID: 4497
• ChEMBL ID: CHEMBL15150
• Mol file: 85146-53-8.mol

Synonyms:arachidonamide;Arachidonoyl amide;85146-53-8;Arachidonoyl amine;Arachidonoylamide;(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenamide;CHEMBL15150;5Z,8Z,11Z,14Z-eicosatetraenoyl amine;Arachidonamide (20:4, n-6);arachidonic acid amide;BSPBio_001537;Arachidonamide(20:4,N-6);SCHEMBL542346;BML2-C08;BCBcMAP01_000148;BNBSCAZCQDLUDU-DOFZRALJSA-N;CHEBI:137830;DTXSID001347885;HMS1361M19;HMS1791M19;HMS1989M19;HMS3402M19;HMS3650G07;5Z,8Z,11Z,14Z-eicosatetraenamide;BDBM50056489;LMFA08010007;IDI1_034007;NCGC00161187-03;NCGC00161187-04;NCGC00161187-05;NCGC00161187-06;5(Z),8(Z),11(Z),14(Z)-eicosatetraenamide;SR-01000946782;SR-01000946782-1;BRD-K29555132-001-02-2;(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid amide

Chemical Property of Arachidonamide

Chemical Property:

• Boiling Point: 462.9±34.0 °C(Predicted)
• PKA: 16.54±0.40(Predicted)
• PSA: 43.09000
• Density: 0.908±0.06 g/cm3(Predicted)
• LogP: 6.31770
• Storage Temp.: ?20°C
• Solubility.: ≤10mg/ml in ethanol;10mg/ml in DMSO;10mg/ml in dimethyl formamide
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 14
• Exact Mass: 303.256214676
• Heavy Atom Count: 22
• Complexity: 364

Purity/Quality:

98%Min ^*data from raw suppliers

Arachidonamide(20:4,n-6) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)N
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N
• Uses: Arachidonamide (20:4, n-6) is a weak cannabinoid CB1 and CB2 agonist.

Technology Process of Arachidonamide

There total 2 articles about Arachidonamide 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:

arachidonoyl chloride (57303-04-5) → arachidonyl amide (85146-53-8)

Guidance literature:

With ammonium hydroxide; In dichloromethane; for 0.25h; Yield given;

DOI:10.1021/jm960752x

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → arachidonyl amide (85146-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 1 h

2: NH₄OH / CH₂Cl₂ / 0.25 h

With ammonium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1021/jm960752x

upstream raw materials:

arachidonoyl chloride

all cis 5,8,11,14-eicosatetraenoic acid