602-41-5

Basic information

• Product Name: THIOCOLCHICOSIDE
• Synonyms: 10-thiocolchicoside;coltramyl;n-(3-(beta-d-glucopyranosyloxy)-5,6,7,9-tetrahydro-1,2-dimethoxy-10-acetamid;r.271;THIOCOLCHICOSIDE;3,10-DI(DEMETHOXY)-3-GLUCOPYRANOSYLOXY-10-METHYLTHIOCOLCHICINE;2-Demethoxy-2-glucosidoxythiocolchisine;Thiocolchisine, 2-glucoside analog
• CAS NO: 602-41-5
• Molecular Formula: C₂₇H₃₃NO₁₀S
• Molecular Weight: 563.62
• EINECS: 210-017-7
• Product Categories: Miscellaneous Biochemicals;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Plant extract
• Mol File: 602-41-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 190-198?C
• Boiling Point: 929.624oC at 760 mmHg
• Flash Point: 516.018oC
• Appearance: /
• Density: 1.2222 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6550 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Methanol (Slightly, Heated), Water (Slightly)
• PKA: 12.74±0.70(Predicted)
• Merck: 14,9324
• CAS DataBase Reference: THIOCOLCHICOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: THIOCOLCHICOSIDE(602-41-5)
• EPA Substance Registry System: THIOCOLCHICOSIDE(602-41-5)

Safety Data

• RTECS: AC2976015
• Hazardous Substances Data: 602-41-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

Uses

A GABA receptor antagonist which is prescribed as a muscle relaxant having analgesic effects.

InChI:InChI=1/C27H33NO10S/c1-12(30)28-16-7-5-13-9-18(37-27-24(34)23(33)22(32)19(11-29)38-27)25(35-2)26(36-3)21(13)14-6-8-20(39-4)17(31)10-15(14)16/h6,8-10,16,19,22-24,27,29,32-34H,5,7,11H2,1-4H3,(H,28,30)/t16-,19+,22+,23-,24+,27+/m0/s1

Upstream product

• 477-29-2 3-de-O-methylcolchicine-3-O-β-Dglucopyranoside 
• 5188-07-8 sodium thiomethoxide 
• 163956-01-2 3-demethyl-3-(2,3,4,5-tetra-O-acetyl-β-D-glucopyranosyl)thiocolchicine 
• 87424-25-7 3-O-demethylthiocolchicine 
• 80-70-6 N,N,N',N'-tetramethylguanidine 
• 492-61-5 β-D-glucose 
• 2730-71-4 thiocolchicine 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 939373-68-9 6'-tosylthiocolchicoside 
• 87424-25-7 3-O-demethylthiocolchicine 
• 939373-74-7 6'-thioacetylthiocolchicoside triacetate 
• 939373-71-4 6'-iodothiocolchicoside triacetate 
• 939373-69-0 6'-tosylthiocolchicoside triacetate 

Relevant articles and documents

PROCESS FOR THE CONVERSION OF COLCHICINOIDS TO THEIR 3-GLYCOSYLATED DERIVATIVES VIA THEIR RESPECTIVE 3-DEMETHYL ANALOGUES

The present invention relates to a bioprocess for the preparation of glycosylated Colchicine, its analogs and derivatives of formula (I) wherein X represents O or S, and R1 represents C1-C6 alkyl, R2 is a glycoside residue, R represents hydrogen, C1-C6 alkyl, formyl or acetyl.

Novel 3-O-glycosyl-3-demethylthiocolchicines as ligands for glycine and γ-aminobutyric acid receptors

New 3-O-glycosyl-3-demethylthiocolchicines containing natural and unnatural sugar moieties were prepared and tested on γ-aminobutyric acid (GABA) and strychnine-sensitive glycine receptors present in rat brain and spinal cord. Two different synthetic approaches were used with the readily available 3-O-demethylthiocolchicine (1b) and thiocolchicoside (2a). Glycosyl compounds 2a-g were obtained from 1b and 1-fluorosugars 4. 6′-Heterosubstituted glycosyl compounds 6-12 and the 6′-desoxy derivative 2h were prepared from 2a.

A process for the glycosidation of colchicine derivatives and products obtained

The present invention relates to a process for the preparation of colchicine or thiocolchicine glycosides or derivatives thereof.