N-(6Z,9Z,12Z-octadecatrienoyl)-ethanolamine

Base Information

• Chemical Name: N-(6Z,9Z,12Z-octadecatrienoyl)-ethanolamine
• CAS No.: 150314-37-7
• Molecular Formula: C20H35NO2
• Molecular Weight: 321.5
• DSSTox Substance ID: DTXSID001202613
• Wikidata: Q76294217
• Metabolomics Workbench ID: 4650
• ChEMBL ID: CHEMBL455997
• Mol file: 150314-37-7.mol

Synonyms:150314-37-7;N-(6Z,9Z,12Z-octadecatrienoyl)-ethanolamine;N-gamma-Linolenoylethanolamine;(6Z,9Z,12Z)-N-(2-hydroxyethyl)octadeca-6,9,12-trienamide;Anandamide (18:3, n-6);N-cis-6,9,12-octadecatrienoylethanolamine;.gamma.-Linolenoyl Ethanolamide;gamma-Linolenoyl-EA;LMFA08040003;gamma-Linoleoyl ethanolamide;CHEMBL455997;SCHEMBL4238398;CHEBI:165585;DTXSID001202613;NAE(18:3);NCGC00161192-02;(6Z,9Z,12Z)-N-(2-Hydroxyethyl)-6,9,12-octadecatrienamide

Chemical Property of N-(6Z,9Z,12Z-octadecatrienoyl)-ethanolamine

Chemical Property:

• PSA: 49.33000
• LogP: 5.07530
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 321.266779359
• Heavy Atom Count: 23
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

N-γ-Linolenoylethanolamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCCCCC(=O)NCCO
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)NCCO
• Uses: N-γ-Linolenoylethanolamine is a member of the endocannabinoids and was found to be a potential inhibitor of cancer cell proliferation.

Technology Process of N-(6Z,9Z,12Z-octadecatrienoyl)-ethanolamine

There total 2 articles about N-(6Z,9Z,12Z-octadecatrienoyl)-ethanolamine 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:

all-cis-6,9,12-octadecatrienoic acid (506-26-3,34615-07-1) → linolenyl ethanolamide (150314-37-7)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride

With oxalyl dichloride;

DOI:10.1021/jm00072a026

Reference yield:

z,z,z-octadeca-6,9,12-trienoyl chloride (54562-14-0) + ethanolamine (141-43-5) → linolenyl ethanolamide (150314-37-7)

Guidance literature:

DOI:10.1021/jm00072a026

upstream raw materials:

z,z,z-octadeca-6,9,12-trienoyl chloride

ethanolamine

all-cis-6,9,12-octadecatrienoic acid

Refernces