16729-47-8

Basic information

• Product Name: (9Z,12Z)-N-(4-hydroxy-3-methoxybenzyl)octadeca-9,12-dienamide
• CAS NO: 16729-47-8
• Molecular Formula: C₂₆H₄₁NO₃
• Molecular Weight: 415.6086
• Mol File: 16729-47-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 599.1°C at 760 mmHg
• Flash Point: 316.1°C
• Density: 0.993g/cm³
• Vapor Pressure: 6.01E-15mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: (9Z,12Z)-N-(4-hydroxy-3-methoxybenzyl)octadeca-9,12-dienamide(CAS DataBase Reference)
• NIST Chemistry Reference: (9Z,12Z)-N-(4-hydroxy-3-methoxybenzyl)octadeca-9,12-dienamide(16729-47-8)
• EPA Substance Registry System: (9Z,12Z)-N-(4-hydroxy-3-methoxybenzyl)octadeca-9,12-dienamide(16729-47-8)

Safety Data

• Hazardous Substances Data: 16729-47-8(Hazardous Substances Data)

Upstream product

• 1196-92-5 Vanillylamin 
• 7459-33-8 linoleyl chloride 
• 60-33-3 linoleic acid 
• 96724-05-9 octadeca-9,12-dienoyl chloride 
• 60-33-3 (9E,12E)-Octadeca-9,12-dienoic acid 

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.

Vanilloids. 1. Analogs of Capsaicin with Antinociceptive and Antiinflammatory Activity

As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion the parent structure (and related compounds derived from homovanillic acid) was varied.In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures were active.Short-chain compounds were active by systemic administration in the assays mentioned above but they retained the high pungency and acute toxicity characteristic of capsaicin.In contrast, the long chain cis-unsaturates, NE-19550 (vanillyloleamide) and NE-28345 (oleylhomovanillamide), were orally active, less pungent, and less acutely toxic than capsaicin.The potential of these compounds as antiinflammatory/analgesic agents is discussed in light of recent data on the mechanism of action of vanilloids on sensory nerve fibers.