Zucapsaicin

Base Information

• Chemical Name: Zucapsaicin
• CAS No.: 25775-90-0
• Molecular Formula: C18H27NO3
• Molecular Weight: 305.417
• Hs Code.: 2924299090
• European Community (EC) Number: 636-760-0
• UNII: 15OX67P384
• DSSTox Substance ID: DTXSID101014453
• Nikkaji Number: J74.699A
• Wikipedia: Zucapsaicin
• Wikidata: Q8074969
• NCI Thesaurus Code: C75078
• Pharos Ligand ID: JALYU77Q7KW4
• Metabolomics Workbench ID: 130577
• ChEMBL ID: CHEMBL313971
• Mol file: 25775-90-0.mol

Synonyms:civamide;zucapsaicin

Chemical Property of Zucapsaicin

Chemical Property:

• Vapor Pressure: 4.41E-11mmHg at 25°C
• Melting Point: 70 °C
• Refractive Index: 1.523
• Boiling Point: 511.462 °C at 760 mmHg
• PKA: 9.76±0.20(Predicted)
• Flash Point: 263.123 °C
• PSA: 58.56000
• Density: 1.042 g/cm³
• LogP: 4.18050
• Storage Temp.: 2-8°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 305.19909372
• Heavy Atom Count: 22
• Complexity: 341

Purity/Quality:

98%,99%, ^*data from raw suppliers

cis-Capsaicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C=CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• Isomeric SMILES: CC(C)/C=C\CCCCC(=O)NCC1=CC(=C(C=C1)O)OC
• Recent ClinicalTrials: Civamide Nasal Solution for Postherpetic Neuralgia of the Trigeminal Nerve
• Description: Zucapsaicin is a topical analgesic that was approved in Canada in July 2010 for use in conjunction with oral COX-2 inhibitors or NSAIDs to relieve severe pain in adults with osteoarthritis of the knee. Zucapsaicin is the cis-isomer of the natural product capsaicin. Capsaicin is available without a prescription in creams, lotions, and patches for the treatment of neuropathic and musculoskeletal pain. Zucapsaicin is available as a 0.075% by weight cream. The advantages of zucapsaicin compared with capsaicin are reported to be a lesser degree of local irritation (stinging, burning, erythema) in patients and a greater degree of efficacy in preclinical animal models of pain. The analgesic action of zucapsaicin and capsaicin is mediated through the transient receptor potential vanilloid type 1 (TRPV1) channel.
• Uses: (Z)-CAPSAICIN is used as a tool in neurobiological research. Prototype vanilloid receptor agonist.
• Clinical Use: Zucapsaicin, the cis-isomer of the natural product capsaicin, is a topical analgesic that was initially developed by Winston Pharmaceuticals and approved in Canada in July 2010 for the treatment of severe pain in adults with osteoarthritis of the knee. The advantages of zucapsaicin compared with naturally-occurring capsaicin are reported to be a lesser degree of local irritation (stinging, burning, erythema) in patients and a greater degree of efficacy in preclinical animal models of pain. The analgesic action of both zucapsaicin and capsaicin is mediated through the transient receptor potential vanilloid type 1 (TRPV1) channel, a ligand-gated ion channel expressed in the spinal cord, brain, and localized on neurons in sensory projections to the skin, muscles, joints, and gut.

Technology Process of Zucapsaicin

There total 12 articles about Zucapsaicin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

Vanillylamin (1196-92-5) + (Z)-8-Methyl-non-6-enoyl chloride (31467-61-5) → cis-capsaicin (25775-90-0,912457-62-6)

Guidance literature:

In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jm00070a002

Reference yield:

C18H25NO3 → cis-capsaicin (25775-90-0,912457-62-6)

Guidance literature:

With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 - 25 ℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Large scale;

Reference yield:

(6Z)-8-methyl-6-nonaneneoic acid (31467-60-4) → cis-capsaicin (25775-90-0,912457-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / 3 h

2: 70 percent / dimethylformamide; diethyl ether

With oxalyl dichloride; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jm00070a002

upstream raw materials:

Vanillylamin

(Z)-8-Methyl-non-6-enoyl chloride

(6Z)-8-methyl-6-nonaneneoic acid

(5-carboxypentyl)triphenylphosphonium bromide

Downstream raw materials:

dihydrocapsaicin

Refernces

• 1、 Janusz, John M.,Buckwalter, Brian L.,Young, Patricia A.,LaHann, Thomas R.,Farmer, Ralph W.,et al.. "Vanilloids. 1. Analogs of Capsaicin with Antinociceptive and Antiinflammatory Activity". . p. 2595 - 2604. Retrieved 2007/10/02.
• 2、 Gannett, Peter M.,Nagel, Donald L.,Reilly, Pam J.,Lawson, Terence,Sharpe, Jody,Toth, Bela. "The Capsaicinoids: Their Separation, Synthesis, and Mutagenicity". . p. 1064 - 1071. Retrieved 2007/10/02.