1954-28-5

Basic information

• Product Name: etoglucid
• Synonyms: etoglucid;Triethylene glycol diglycidyl ether.;Ethoglucid;2,2'-(2,5,8,11-Tetraoxa-1,12-dodecanediyl)bisoxirane;Epodyl;Etoglucide;ICI-32865;2-[2-[2-(2-glycidoxyethoxy)ethoxy]ethoxymethyl]oxirane
• CAS NO: 1954-28-5
• Molecular Formula: C₁₂H₂₂O₆
• Molecular Weight: 262.34
• EINECS: 217-784-7
• Mol File: 1954-28-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: -15 to -11°
• Boiling Point: bp0.005 140°; bp0.1 133-149°; bp2 195-197°
• Flash Point: 145°C
• Appearance: /
• Density: d20 1.1312
• Vapor Pressure: 6.02E-05mmHg at 25°C
• Refractive Index: nD20 1.4584
• CAS DataBase Reference: etoglucid(CAS DataBase Reference)
• NIST Chemistry Reference: etoglucid(1954-28-5)
• EPA Substance Registry System: etoglucid(1954-28-5)

Safety Data

• Hazardous Substances Data: 1954-28-5(Hazardous Substances Data)

Usage

Safety Profile

Moderately toxic byintraperitoneal route. Questionable carcinogen withexperimental neoplastigenic data. A skin irritant. Whenheated to decomposition it emits acrid smoke andirritating fumes.

InChI:InChI=1/C12H22O6/c1(13-3-5-15-7-11-9-17-11)2-14-4-6-16-8-12-10-18-12/h11-12H,1-10H2

Upstream product

• 90736-68-8 4,7,10,13-tetraoxahexadeca-1,15-diene 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 106-89-8 epichlorohydrin 

Downstream Products

• 156366-11-9 1-[2-(2-{2-[2-Hydroxy-3-(4-vinyl-phenoxy)-propoxy]-ethoxy}-ethoxy)-ethoxy]-3-(4-vinyl-phenoxy)-propan-2-ol 

Relevant articles and documents

Facile Synthesis of Hydroxy-Substituted Thiacrown Ethers via Nucleophilic Ring Opening of Epoxides

The title thiacrown ethers were prepared in a one-step procedure to give a series of unique macrocycles possessing two unsubstituted hydroxy groups that can be easily functionalized. In addition, epoxides and macrocycles derived from Cookson's birdcage diketone, were prepared. The nucleophilic ring opening of epoxides synthesis can be classified in the frame of click chemistry. Surprisingly, some of the prepared allyl substituted polyglycols as well as bis-epoxides, especially sulfur analogues, were prepared for the first time.

Application of HPLC for the screening of separation of new macrocyclic systems

The efficient synthesis of new macrocyclic systems via nucleophilic ring opening reaction of epoxides by thiols was described. Initially new macrocyclic compounds were obtained as a mixture of diastereomers. Preparative thin layer chromatography was applied to separate meso and pairs of enantiomer. The identification of products using a chiral HPLC column and mass spectroscopy was utilized.

Diol glycidyl ether-bridged cyclens: Preparation and their applications in gene delivery

Polymeric 1,4,7,10-tetraazacyclododecanes (cyclens) using diol glycidyl ether with different chain length as bridges (5a-e) were designed and synthesized from various diols, 1,7-diprotected cyclen and epichlorohydrin. The molecular weights of the title polymers were measured by GPC with good polydispersity. Agarose gel retardation and fluorescent titration using ethidium bromide showed good DNA-binding ability of 5. They could retard plasmid DNA (pDNA) at an N/P ratio of 4-6 and form polyplexes with sizes around 100-250 nm from an N/P ratio of 10 to 60 and relatively low zeta-potential values (5-22 mV). The cytotoxicity of 5 assayed by MTT is much lower than that of 20 kDa PEI. In vitro transfection against A549 and 293 cells showed that the transfection efficiency (TE) of 5c/DNA polyplexes is close to that of 20 kDa PEI at an N/P ratio of 5. Structure-activity relationship (SAR) of 5 was discussed in their DNA-binding, cytotoxicity, and transfection studies. The TE of 5c/DNA polyplexes could be improved by the introduction of 50 μM of chloroquine, the endosomolytic agents, to pretreated cells. These studies may extend the application areas of macrocyclic polyamines, especially for cyclen.