Demecolceine

Base Information

• Chemical Name: Demecolceine
• CAS No.: 518-11-6
• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.406
• Wikidata: Q104918732
• Mol file: 518-11-6.mol

Synonyms:Demecolceine;Colchameine;COLCHICEINE, N-DEACETYL-N-METHYL-;NSC 36559;518-11-6;10-hydroxy-1,2,3-trimethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one;Benzo(a)heptalen-9(5H)-one, 6,7-dihydro-10-hydroxy-1,2,3-trimethoxy-7-(methylamino)-, (S)-;(7s)-9-hydroxy-1,2,3-trimethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-10(5h)-one;(7S)-10-hydroxy-1,2,3-trimethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one;ATWWYGQDYGSWQA-UHFFFAOYSA-N;Colchiceine, N-desacetyl-N-methyl-;LS-54659;Colchiceine, 7-deacetamido-7-(methylamino)-;FT-0665682;10-Hydroxy-1,2,3-trimethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-9(5H)-one #

Chemical Property of Demecolceine

Chemical Property:

• Vapor Pressure: 1.48E-16mmHg at 25°C
• Melting Point: 120-122°C
• Boiling Point: 626.4°C at 760 mmHg
• Flash Point: 332.6°C
• PSA: 77.02000
• Density: 1.27g/cm³
• LogP: 3.04280
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 357.15762283
• Heavy Atom Count: 26
• Complexity: 638

Purity/Quality:

99% ^*data from raw suppliers

Demecolceine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)O)OC)OC)OC
• Description: One of the colchicine alkaloids, demecolceine has been isolated from the corms and seeds of Colchicum autumnale, Gloriosa virescens and Littoria modesta. It forms colourless rods when crystallized from EtOH and has a specific rotation of [α]D - 223° (CHC13)·
• Uses: An antimitotic agent that disrupts microtubles by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway.

Technology Process of Demecolceine

There total 6 articles about Demecolceine 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:

(-)-demecolcine (477-30-5) → demecolceine (518-11-6,14917-53-4)

Guidance literature:

With hydrogenchloride;

DOI:10.1002/hlca.19540370104

Reference yield:

colchicine (64-86-8,54192-66-4) → demecolceine (518-11-6,14917-53-4)

Guidance literature:

Multi-step reaction with 4 steps

1: aqueous HCl

2: CH₂Cl₂; diethyl ether

3: benzene

4: aqueous HCl

With hydrogenchloride; diethyl ether; dichloromethane; benzene;

DOI:10.1002/hlca.19540370104

Reference yield:

deacetylcolchicine (3476-50-4) → demecolceine (518-11-6,14917-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene

2: aqueous HCl

With hydrogenchloride; benzene;

DOI:10.1002/hlca.19540370104

upstream raw materials:

(-)-demecolcine

colchicine

deacetylcolchicine

colchiceine

Downstream raw materials:

isodemecolcine

(-)-demecolcine