7336-36-9

Basic information

• Product Name: 2-DEMETHYLCOLCHICINE
• Synonyms: 2-DEMETHYLCOLCHICINE;(S)-7-Acetylamino-6,7-dihydro-2-hydroxy-1,3,10-trimethoxybenzo[a]heptalen-9(5H)-one;N-[(7S)-2-hydroxy-1,3,10-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS NO: 7336-36-9
• Molecular Formula: C₂₁H₂₃NO₆
• Molecular Weight: 385.41
• Mol File: 7336-36-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 125°C
• Boiling Point: 512.62°C (rough estimate)
• Flash Point: 417.1°C
• Appearance: /
• Density: 1.2875 (rough estimate)
• Refractive Index: 1.5614 (estimate)
• CAS DataBase Reference: 2-DEMETHYLCOLCHICINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-DEMETHYLCOLCHICINE(7336-36-9)
• EPA Substance Registry System: 2-DEMETHYLCOLCHICINE(7336-36-9)

Safety Data

• Hazardous Substances Data: 7336-36-9(Hazardous Substances Data)

Usage

General Description

2-Demethylcolchicine is a natural compound that belongs to the colchicine family and is a derivative of colchicine. It is an alkaloid compound found in the autumn crocus and other plants in the Colchicaceae family. This chemical is known for its anti-inflammatory and anti-tumor properties, making it a potential candidate for the treatment of various diseases, including cancer. Research has shown that 2-Demethylcolchicine exhibits similar biological activities to colchicine, but with reduced toxicity, making it a promising alternative for therapeutic applications. Additionally, its unique structural features make it a valuable molecule for pharmaceutical development and drug design.

Upstream product

• 64-86-8 colchicine 
• 186581-53-3 diazomethane 
• 33530-04-0 2,10-didemethylcolchicine 

Downstream Products

• 78231-83-1 1,2-O-didemethylcolchicine 
• 86436-31-9 2-O-(N-phenyltetrazolyl)-2-demethylcolchicine 

Relevant articles and documents

Four new colchicinoids, gloriosamines A-D, from Gloriosa rothschildiana

Four new colchicinoids, gloriosamines A-D, were isolated from the aerial parts of Gloriosa rothschildiana. The structure of gloriosamine A, including the absolute configuration, was determined by chemical conversion from colchicine.

PHENOLIC CONGENERS OF COLCHICINE: PREPARATION AND CHARACTERIZATION OF PHENOLIC AND CATECHOLIC ANALOGUES OF COLCHICINE, COLCHICEINE AND THIOCOLCHICINE

Treatment of 2-demethylcolchicine (2) with sulfuric acid afforded 1,2-didemethylcolchicine (6) as the major, and 2,3-didemethylcolchicine (8) as the minor product. 2,3-Didemethylcolchicine (8) was prepared from 3-ethoxycarbonyl-3-demethylcolchicine by sulfuric acid treatment.Hydrolysis of catecholic compounds 6 and 8 with 0.1 N hydrochloric acid afforded colchiceines 13 and 14, respectively.Ester derivatives of 2-demethyl- and 3-demethylcolchicine, and of catechols 6 and 8 were prepared.A direct conversion of 3 into 3-demethylthiocolchicine (15) and conversion of 15 into ester derivatives is described.Cleavage of the ether groups of colchicine by boron tribromide is also reported.

Synthesis of Two Aromatic Methylenedioxy-Substituted Colchicine Congeners: Elucidation of the Structure of Cornigerine as 2,3-(Methylenedioxy)-2,3-Didemethoxycolchicine

Treatment of colchicine with concentrated sulfuric acid at 80-90 deg C afforded besides 2-demethylcolchicine a mixture of catecholic colchicines which could be separated and identified.Similar treatment of 1-demethyl- and 3-demethylcolchicine gave predominantly the 1,2-catechol or its 2,3 isomer.Methylenation of these catechols afforded the colchicine congeners 1 and 10.A comparison with natural cornigerine revealed that the alkaloid was identical with the 2,3-methylenedioxy compound 10 and not with 1, as formerly proposed.