53283-50-4

Basic information

• Product Name: 4-acetoxy-3-methoxyphenylacetyl chloride
• Synonyms: 4-acetoxy-3-methoxyphenylacetyl chloride
• CAS NO: 53283-50-4
• Molecular Weight: 242.659
• Mol File: 53283-50-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-acetoxy-3-methoxyphenylacetyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-acetoxy-3-methoxyphenylacetyl chloride(53283-50-4)
• EPA Substance Registry System: 4-acetoxy-3-methoxyphenylacetyl chloride(53283-50-4)

Safety Data

• Hazardous Substances Data: 53283-50-4(Hazardous Substances Data)

Upstream product

• 306-08-1 Homovanillic acid 
• 5447-38-1 2-(4-acetoxy-3-methoxyphenyl)acetic acid 

Downstream Products

• 107512-56-1 NE 28345 
• 58418-73-8 N-Octylhomovanillamide 
• 107512-61-8 N-Dec-9-enyl-2-(4-hydroxy-3-methoxy-phenyl)-acetamide 
• 107512-63-0 2-(4-Hydroxy-3-methoxy-phenyl)-N-nonyl-acetamide 
• 53283-46-8 N-Heptyl-2-(4-hydroxy-3-methoxy-phenyl)-acetamide 
• 150988-93-5 N-Hexyl-2-(4-hydroxy-3-methoxy-phenyl)-acetamide 
• 53283-42-4 N-Dodecylhomovanillamide 
• 107512-66-3 N-Cyclooctyl-2-(4-hydroxy-3-methoxy-phenyl)-acetamide 
• 149623-46-1 Acetic acid 4-{[2-(4-chloro-phenyl)-ethylcarbamoyl]-methyl}-2-methoxy-phenyl ester 
• 53283-37-7 Acetic acid 4-heptylcarbamoylmethyl-2-methoxy-phenyl ester 
• 107533-12-0 N-oleyl-4-acetoxy-3-methoxyphenylacetamide 

Relevant articles and documents

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.

Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic 'A-region'

A series of analogues of capsaicin, the pungent principle of chilli peppers, was synthesized and tested in assays for capsaicin-like agonism in vitro. The results of these assays were compared with activities in an acute nociceptive model and a correlation was observed which established that the results of these in vitro assays were predictive of analgesia. Using a modular approach the structure-activity profile of specific regions of capsaicin congeners was established using an in vitro assay measuring 45Ca2+ uptake into neonatal rat dorsal root ganglia neurones. Substituted benzylnonanamides 2a-z and N-octyl-substituted phenylacetamides 4a-v were made to test the requirements for activity in the aromatic 'A-region' of the molecule. Compounds with the natural substitution pattern (2b and 4c) and the corresponding catechols (2i and 4g) were the most potent, although the catechols were less potent in vivo. Other substitution patterns have reduced activity. These results have established stringent structural requirements for capsaicin-like activity in this part of the molecule.