Deacetylcolchiceine

Base Information

• Chemical Name: Deacetylcolchiceine
• CAS No.: 3482-37-9
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.379
• NSC Number: 36796
• DSSTox Substance ID: DTXSID90875143
• Wikidata: Q27166959
• ChEMBL ID: CHEMBL3729937
• Mol file: 3482-37-9.mol

Synonyms:Deacetylcolchiceine;(R/S)-N-Deacetyl Colchiceine;68296-64-0;7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one;Deacetylcholchiceine;Desacetylcholchiceine;Colchiceine, N-deacetyl-;Colchicinic acid, trimethyl-;Colchiceine, N-deacetyl- (VAN);NSC36796;NSC-36796;Prestwick_353;Prestwick0_000580;Prestwick1_000580;Prestwick2_000580;Desacetylcolchiceine;N-Deacetylcolchiceine;NSC 36796;Oprea1_221824;SPBio_002619;SCHEMBL1822222;CHEMBL3729937;CHEBI:95161;DTXSID90875143;HMS1569D22;CCG-231728;LS-54693;FT-0665493;FT-0665494;WLN: L B677 MV&T&J CO1 DO1 EO1 JZ NQ;Q27166959;Benzo[a]heptalen-9(5H)-one,7-dihydro-10-hydroxy-1,2,3-trimethoxy-, (S)-

Chemical Property of Deacetylcolchiceine

Chemical Property:

• Vapor Pressure: 1.09E-16mmHg at 25°C
• Melting Point: >230°C (dec.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 629°Cat760mmHg
• Flash Point: 334.2°C
• PSA: 91.01000
• Density: 1.32g/cm³
• LogP: 3.09150
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly), Ethanol (Slightly), Methanol
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 343.14197277
• Heavy Atom Count: 25
• Complexity: 623

Purity/Quality:

99% ^*data from raw suppliers

N-Deacetyl Colchiceine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C(=C2C(=C1)CCC(C3=CC(=O)C(=CC=C32)O)N)OC)OC
• Description: A minor alkaloid of the colchicine class, this base was first isolated from the seeds and corms of Colchicum autumnale, Gloriosa virescens and Littoria modesta and subsequently by Russian workers from Merendera robusta Bge. Several specific rotations have been measured, e.g. [α]D - 184°, - 152° and - 180° (all in CHC13). The base is separated from the numerous accompanying alkaloids by chromatography and countercurrent distribution.
• 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 Deacetylcolchiceine

There total 11 articles about Deacetylcolchiceine 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: 80.5%

colchicine (64-86-8,54192-66-4) → trimethylcolchicinic acid (3482-37-9,2731-31-9)

Guidance literature:

With sulfuric acid; water; for 5h; Heating;

DOI:10.1002/hlca.19950780517

Reference yield:

colchiceine (477-27-0,1990-46-1) → trimethylcolchicinic acid (3482-37-9,2731-31-9)

Guidance literature:

With hydrogenchloride;

DOI:10.1002/hlca.19540370104

Reference yield:

7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one (73307-44-5,68296-64-0) → trimethylcolchicinic acid (3482-37-9,2731-31-9)

Guidance literature:

With camphor-10-sulfonic acid;

DOI:10.1002/hlca.19570400123

upstream raw materials:

colchicine

(7S)-isocolchicine

colchiceine

7-amino-10-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[a]heptalen-9-one

Downstream raw materials:

colchifoline

7-oxodeacetamidoisocolchicine

7-desacetamido-7-oxocolchicine

colchiceine

Refernces

• 1、 Korde, Aruna,Satpati, Drishty,Mathur, Anupam,Mallia, Madhava,Banerjee, Sharmila,Kothari, Kanchan,Sarma,Choudhari, Pradeep,Venkatesh, Meera. "99mTc-labeling of colchicine using [99mTc(CO) 3(H2O)3]+ and [ 99mTc≡N]2+ core for the preparation of potential tumor-targeting agents". . p. 793 - 799. Retrieved 2007/10/03.
• 2、 Kouroupis, Pavlos,Hansen, Hans-Jurgen. "100. From Colchicine and Some of Its Derivatives to 1,2,3,9,10-Pentamethoxybenzoheptalenes". . p. 1247 - 1277. Retrieved 2007/10/02.