150314-34-4

Basic information

• Product Name: DIHOMO-GAMMA-LINOLENYLETHANOLAMIDE
• Synonyms: ANANDAMIDE;HEA;DIHOMO-GAMMA-LINOLENOYL ETHANOLAMIDE;DIHOMO-GAMMA-LINOLENYLETHANOLAMIDE;N-(2-HYDROXYETHYL)-8Z,11Z,14Z-EICOSATRIENAMIDE;homo-gamma-linolenylethanolamide;(Z,Z,Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide;8,11,14-Eicosatrienamide, N-(2-hydroxyethyl)-, (Z,Z,Z)-
• CAS NO: 150314-34-4
• Molecular Formula: C22H39NO2
• Molecular Weight: 349.55
• Mol File: 150314-34-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 522.1°Cat760mmHg
• Flash Point: 269.5°C
• Appearance: /
• Density: 0.929g/cm³
• Vapor Pressure: 4.41E-13mmHg at 25°C
• Refractive Index: 1.493
• PKA: 14.49±0.10(Predicted)
• CAS DataBase Reference: DIHOMO-GAMMA-LINOLENYLETHANOLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIHOMO-GAMMA-LINOLENYLETHANOLAMIDE(150314-34-4)
• EPA Substance Registry System: DIHOMO-GAMMA-LINOLENYLETHANOLAMIDE(150314-34-4)

Safety Data

• Hazardous Substances Data: 150314-34-4(Hazardous Substances Data)

Usage

Uses

(8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide is an endocannabinoid that binds to recombinant human CB1 and CB2 receptors. (8Z,11Z,14Z)-N-(2-Hydroxyethyl)-8,11,14-eicosatrienamide is a CB1 and CB2 agonist and an adenylyl cyclase inhibitor.

InChI:InChI=1/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6+,10-9+,13-12+

Upstream product

• 7324-41-6 cis-8,11,14-eicosatrienoic acid 
• 141-43-5 ethanolamine 
• 126104-52-7 di-homo-gamma-linolenyl chloride 

Relevant articles and documents

Structure-Activity Relationships of Fish Oil Derivatives with Antiallergic Activity in Vitro and in Vivo

A series of unsaturated fatty acids in fish oil and their corresponding ethanolamide metabolites were explored to find active fish oil components of antiallergic activity in vitro. Ethanolamides of omega-3 fatty acids (α-linolenic acid, EPA, and DHA) were found to possess promising antiallergic activity, whereas free fatty acids and ethanolamides of other fatty acids exhibited no or weak potency. Based on this finding, structure-activity relationships of DHA-ethanolamide (DHEA) derivatives were investigated to yield better fatty acid derivatives with enhanced antiallergic activity in vitro and in vivo. When the ethanolamide moiety of DHEA was replaced by the substituted sulfonamide functionality, highly promising potency was provided in vitro. Compound 59 showed improved antiallergic activity in vivo over DHEA. The results indicate that optimized DHEA derivatives have enhanced antiallergic activity in vitro and in vivo, and the resulting structures will be an important basis for further development of bioavailable derivatives with promising allergy suppressive activity.