129024-87-9

Basic information

• Product Name: (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide
• Synonyms: 4,7,10,13,16,19-docosahexaenamide, N-[2-(3,4-dihydroxyphenyl)ethyl]-, (4Z,7Z,10Z,13Z,16Z,19Z)-
• CAS NO: 129024-87-9
• Molecular Formula: C₃₀H₄₁NO₃
• Molecular Weight: 463.6514
• Mol File: 129024-87-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 659.2°C at 760 mmHg
• Flash Point: 352.5°C
• Density: 1.03g/cm³
• Vapor Pressure: 5.51E-18mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide(CAS DataBase Reference)
• NIST Chemistry Reference: (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide(129024-87-9)
• EPA Substance Registry System: (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide(129024-87-9)

Safety Data

• Hazardous Substances Data: 129024-87-9(Hazardous Substances Data)

Usage

Description

(4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide is a long-chain amide molecule with a 22-carbon chain featuring multiple double bonds. It also includes a dihydroxyphenyl group connected to the carbon chain via an ethyl group. This lipid-like molecule, due to its structural resemblance to naturally occurring lipids, may possess potential biological activities and could be involved in various cellular processes. Its unique structure and properties also suggest possible therapeutic applications, although further research is necessary to fully understand its specific functions and potential uses.

Uses

Used in Pharmaceutical Industry:
(4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide is used as a potential therapeutic agent for its possible involvement in various cellular processes. Its unique structure and properties may offer new avenues for the development of treatments targeting specific biological pathways.
Used in Research and Development:
In the field of research and development, (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide serves as a valuable compound for studying its structural and functional similarities to naturally occurring lipids. This can lead to a better understanding of cellular processes and the discovery of new therapeutic approaches.
Used in Cosmetics Industry:
Given its lipid-like nature, (4Z,7Z,10Z,13Z,16Z,19Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]docosa-4,7,10,13,16,19-hexaenamide may also find applications in the cosmetics industry, potentially being utilized in the development of skincare products that aim to mimic or enhance the skin's natural lipid barrier for improved hydration and protection.

Upstream product

• 1220710-22-4 2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethan-1-amine 
• 160801-26-3 N-hydroxysuccinimide DHA ester 
• 1220710-21-3 N-(2-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)ethyl)-2,2,2-trifluoroacetamide 
• 1220710-18-8 Phth-dopamine(acetonide) 
• 57894-18-5 2-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-dioxoisoindoline 
• 65846-04-0 N-<2-(3,4-Dihydroxyphenyl)ethyl>trifluoracetamid 
• 62-31-7 dopamine hydrochloride 
• 51-61-6 dopamine 
• 6217-54-5 docosahexaenoic acid 
• 1220710-23-5 DHA-dopamine(acetonide) 
• 645-31-8 3-hydroxytyramine hydrobromide 
• 98770-66-2 docosahexaenoic acid anhydride 

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.

Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads

A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1β, IL-6, and TNF-α) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-γ-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 ～2 μM). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1β, IL-6, and TNF-α) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads.

Synthesis and biological evaluation of novel amides of polyunsaturated fatty acids with dopamine

New amides of different fatty acids from the C18, C20, and C22 series with dopamine were synthesized. Pharmacological characterization in binding assays with rat brain membrane preparations and in the 'tetrad' of cannabinoid behavioral tests showed that, for these compounds, cannabinoid-like activity was dependent on the fatty acid moiety. Our data demonstrate that polyenoic fatty acid amides with dopamine comprise a new family of synthetic cannabimimetics.