69693-13-6

Basic information

• Product Name: Hexadecanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-
• CAS NO: 69693-13-6
• Molecular Formula: C24H41NO3
• Molecular Weight: 391.594
• Mol File: 69693-13-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Hexadecanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Hexadecanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-(69693-13-6)
• EPA Substance Registry System: Hexadecanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-(69693-13-6)

Safety Data

• Hazardous Substances Data: 69693-13-6(Hazardous Substances Data)

Usage

General Description

Hexadecanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]- is a chemical compound with a molecular formula C25H43NO3. It is also known as N-p-coumaroyl serotonin and is categorized as an amide and a fatty acid derivative. This chemical is an amide of hexadecanoic acid and is characterized by a 4-hydroxy-3-methoxyphenyl moiety attached to the amide nitrogen. It is known to have potential pharmacological effects, as it has been studied for its anti-inflammatory, anti-oxidant, and neuroprotective properties. Additionally, it has been shown to exhibit analgesic and anti-nociceptive effects in some studies. Overall, Hexadecanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]- is a compound with potential therapeutic applications.

Upstream product

• 1196-92-5 Vanillylamin 
• 112-67-4 n-hexadecanoyl chloride 
• 7149-10-2 vanillylamine hydrochloride 
• 57-10-3 1-hexadecylcarboxylic acid 
• 2874-33-1 vanillin oxime 
• 124-10-7 methyl myristoate 
• 112-39-0 hexadecanoic acid methyl ester 
• 69693-12-5 N-(4-hydroxy-3-methoxybenzyl)tetradecanamide 

Relevant articles and documents

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.

Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system

Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 system under mild conditions. For C4-C18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction.