189939-61-5

Basic information

• Product Name: PALMITOYLISOPROPYLAMIDE
• Synonyms: N-(1-METHYLETHYL)-HEXADECANAMIDE;PALMITOYLISOPROPYLAMIDE;PALMITOYL N-ISOPROPYLAMIDE;N-ISOPROPYL-HEXADECANAMIDE;HexadecanaMide, N-(1-Methylethyl)-
• CAS NO: 189939-61-5
• Molecular Formula: C19H39NO
• Molecular Weight: 297.52
• Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols;Inhibitors;Cannabinoid receptor
• Mol File: 189939-61-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 356.5°C at 760 mmHg
• Flash Point: 223.7°C
• Appearance: /
• Density: 0.853g/cm³
• Vapor Pressure: 2.9E-05mmHg at 25°C
• Refractive Index: 1.45
• Storage Temp.: Store at RT
• Solubility: DMSO, Ethanol
• CAS DataBase Reference: PALMITOYLISOPROPYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PALMITOYLISOPROPYLAMIDE(189939-61-5)
• EPA Substance Registry System: PALMITOYLISOPROPYLAMIDE(189939-61-5)

Safety Data

• Hazardous Substances Data: 189939-61-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 189939-61-5 differently. You can refer to the following data:
1. An inhibitor of fatty acid amide hydrolase (FAAH). pIC50=4.89 for inhibition of [3H]-anandamide metabolism. Displays little binding to CB1 and CB2 receptors (IC50>100uM) and very weakly blocks ananad amide uptake (IC50~100uM). Inhibits proliferation of C6 glioma cells.
2. An inhibitor of fatty acid amide hydrolase (FAAH). pIC50=4.89 for inhibition of [3H]-anandamide metabolism. Displays little binding to CB1 and CB2 receptors (IC50>100uM) and very weakly blocks ananadamide uptake (IC50~100uM). Inhibits proliferation of C6 glioma cells.

Biological Activity

Inhibitor of fatty acid amide hydrolase (FAAH); pIC 50 = 4.89 for inhibition of [ 3 H]-anandamide metabolism. Displays little binding to CB 1 and CB 2 receptors (IC 50 > 100 μ M) and very weakly blocks anandamide uptake (IC 50 ~ 100 μ M). Inhibits proliferation of C6 glioma cells.

InChI:InChI=1/C19H39NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(21)20-18(2)3/h18H,4-17H2,1-3H3,(H,20,21)

Upstream product

• 75-31-0 isopropylamine 
• 112-67-4 n-hexadecanoyl chloride 
• 57-10-3 1-hexadecylcarboxylic acid 

Relevant articles and documents

Effects of synthetic alkamides on Arabidopsis fatty acid amide hydrolase activity and plant development

Alkamides and N-acylethanolamines (NAEs) are bioactive, amide-linked lipids that influence plant development. Alkamides are restricted to several families of higher plants and some fungi, whereas NAEs are widespread signaling molecules in both plants and animals. Fatty acid amide hydrolase (FAAH) has been described as a key contributor to NAE hydrolysis; however, no enzyme has been associated with alkamide degradation in plants. Herein reported is synthesis of 12 compounds structurally similar to a naturally occurring alkamide (N-isobutyl-(2E,6Z,8E)decatrienamide or affinin) with different acyl compositions more similar to plant NAEs and various amino alkyl head groups. These "hybrid" synthetic alkamides were tested for activity toward recombinant Arabidopsis FAAH and for their effects on plant development (i.e., cotyledon expansion and primary root length). A substantial increase in FAAH activity was discovered toward NAEs in vitro in the presence of some of these synthetic alkamides, such as N-ethyllauroylamide (4). This "enhancement" effect was found to be due, at least in part, to relief from product inhibition of FAAH by ethanolamine, and not due to an alteration in the oligomerization state of the FAAH enzyme. For several of these alkamides, an inhibition of seedling growth was observed with greater results in FAAH knockouts and less in FAAH over-expressing plants, suggesting that these alkamides could be hydrolyzed by FAAH in planta. The tight regulation of NAE levels in vivo appears to be important for proper seedling establishment, and as such, some of these synthetic alkamides may be useful pharmacological tools to manipulate the effects of NAEs in situ.

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.