Compounds > triglyme
Page last updated: 2024-12-05

triglyme

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Triglyme, also known as tris(2-methoxyethyl) ether, is a non-toxic, colorless liquid with a high boiling point and low viscosity. It is a highly polar aprotic solvent with excellent solvating properties for a wide range of compounds. It is commonly used as a solvent in various chemical reactions, including polymerization, metal complexation, and organic synthesis. Triglyme is also used as a dielectric fluid in capacitors and as a plasticizer in polymers. Its synthesis involves the condensation reaction of ethylene glycol with 2-methoxyethanol. Triglyme is studied due to its unique properties as a solvent, its biocompatibility, and its potential applications in various fields such as lithium-ion batteries, fuel cells, and pharmaceutical synthesis. Its high polarity allows for the dissolution of a wide range of ionic compounds, and its low viscosity ensures rapid mass transfer in reactions. Triglyme is particularly relevant in lithium-ion batteries due to its ability to dissolve lithium salts, enhancing conductivity and battery performance.'

triglyme : A polyether that consists of dodecane in which the carbon atoms at positions 2, 5, 8 and 11 are replaced by oxygen atoms. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID8189
CHEMBL ID1235255
CHEBI ID44842
SCHEMBL ID16126
MeSH IDM0151527

Synonyms (62)

Synonym
CHEMBL1235255
glyme-3
nsc-66400
ethane,2-bis(2-methoxyethoxy)-
triglyme
glyme-4
112-49-2
triethylene glycol dimethyl ether
ansul ether 161
nsc66400
2,8,11-tetraoxadodecane
1,2-bis(2-methoxyethoxy)ethane
2,5,8,11-tetraoxadodecane
pg5 ,
1-methoxy-2-[2-(2-methoxy-ethoxy]-ethane
nsc 66400
brn 1700630
tegdime
ethane, 1,2-bis(2-methoxyethoxy)-
einecs 203-977-3
ai3-28582
glycol, triethylene-, dimethyl ether
DB02078
1-methoxy-2-[2-(2-methoxyethoxy)ethoxy]ethane
dimethyl ether of triethylene glycol
NCGC00164017-01
CHEBI:44842 ,
glyme 4
B0496
FT-0659858
A802587
NCGC00164017-02
AKOS009158244
unii-32yxg88kk0
ec 203-977-3
32yxg88kk0 ,
dtxsid8026224 ,
tox21_300509
cas-112-49-2
dtxcid206224
NCGC00254323-01
SCHEMBL16126
triglyme [mi]
1,2-bis(methoxyethoxy)ethane
(ch3o(ch2)2och2)2
triethylene glycol dimethyl ether (stabilized with bht)
triethylene glycol dimethylether
triethyleneglycol dimethyl ether
mfcd00008504
triethylene glycol dimethyl ether, analytical reference material
triethylene glycol dimethyl ether, reagentplus(r), 99%
triethylene glycol dimethyl ether, vetec(tm) reagent grade, 98%
FT-0755020
E75964
1,2-bis(2-methoxyethoxy) ethane, reagent
Q2453066
2,5,8,11-tetraoxadodecane;1,2-bis(2-methoxyethoxy)ethane;triethylene glycol dimethyl ether;1,2bis(2methoxyethoxy)ethane;triethylene glycoldimethylether (tegdme);2,5,8,11-tetraoxadodecane 1,2-bis(2-methoxyethoxy)ethane triethylene glycol dimethyl ether 1,2
1-methoxy-2-[2-(2-methoxy-ethoxy)-ethoxy]-ethane
EN300-40253
triethylene glycol dimethyl ether 100 microg/ml in acetonitrile
CS-W017328
Z409380232

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In summary, oral administration of triEGdiME during major organogenesis produced only marginal signs of altered maternal status, as evidenced by an increase in maternal liver weight, and caused selective adverse effects upon fetal growth and morphological development at doses greater than or equal to 500 mg/kg/day."( The developmental toxicity of triethylene glycol dimethyl ether in mice.
George, JD; Kimmel, CA; Marr, MC; Price, CJ, 1987)		0.27

Dosage Studied

ExcerptRelevanceReference
"The Rai and Van Ryzin dose-response model proposed for teratology experiments has been characterized for its appropriateness and applicability in modeling the dichotomous response data from developmental toxicity studies."( Characterization of a developmental toxicity dose-response model.
Faustman, EM; Kimmel, CA; Smith, WP; Wellington, DG, 1989)		0.28
"Time-mated CD-1 mice were orally dosed on gestation day 11 (plug = 0) with distilled water (control) or one of four glycol ethers at a dose of 4 mmol/kg: ethylene glycol monomethyl ether (EGME, 304 mg/kg), ethylene glycol dimethyl ether (EGdiME, 361 mg/kg), diethylene glycol dimethyl ether (diEGdiME, 537 mg/kg), triethylene glycol dimethyl ether (triEGdiME, 713 mg/kg)."( Relative potency of four ethylene glycol ethers for induction of paw malformations in the CD-1 mouse.
Eisenmann, CJ; Hardin, BD, 1987)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
solventA liquid that can dissolve other substances (solutes) without any change in their chemical composition.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
polyetherAny ether that contains more than one ether linkage.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency0.00110.023723.228263.5986AID588543
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency38.57080.000627.21521,122.0200AID720636
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (30.00)18.7374
1990's3 (30.00)18.2507
2000's2 (20.00)29.6817
2010's1 (10.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.83

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.83 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index59.80 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ethylene glycol
Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.		1.9710ethanediol;
glycol		metabolite;
mouse metabolite;
solvent;
toxin
theophylline
[no description available]		1.9710dimethylxanthineadenosine receptor antagonist;
anti-asthmatic drug;
anti-inflammatory agent;
bronchodilator agent;
drug metabolite;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
fungal metabolite;
human blood serum metabolite;
immunomodulator;
muscle relaxant;
vasodilator agent
ethylenediamine
ethylenediamine: RN given refers to parent cpd; edamine is the recommended contraction for the ethylenediamine radical. ethylenediamine : An alkane-alpha,omega-diamine in which the alkane is ethane.		2.0310alkane-alpha,omega-diamineGABA agonist
methyl cellosolve
methyl cellosolve: widely used industrial solvent for resins, lacquers, dyes & inks; may cause anemia macrocytosis, appearance of young granulocytes in blood; RN given refers to parent cpd		1.9710glycol etherprotic solvent;
solvent
1,2-dimethoxyethane
1,2-dimethoxyethane: RN given refers to cpd with specified locants for methoxy moieties. 1,2-dimethoxyethane : A diether that is the 1,2-dimethyl ether of ethane-1,2-diol.		1.9710diethernon-polar solvent
diglyme
diglyme : A polyether that is the dimethyl ether derivative of diethylene glycol.		2.940polyetherenvironmental contaminant;
solvent;
xenobiotic
triethylene glycol
triethylene glycol : A poly(ethylene glycol) that is octane-1,8-diol in which the carbon atoms at positions 3 and 6 have been replaced by oxygen atoms.		1.9810diol;
poly(ethylene glycol);
primary alcohol		plasticiser
diethylhexyl phthalate
Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.		1.9710diester;
phthalate ester		androstane receptor agonist;
apoptosis inhibitor;
plasticiser
tetraglyme
[no description available]		2.110polyether
hydroxyethyl methacrylate
hydroxyethyl methacrylate: many of cited refs are for gel which refers to polymeric form of above cpd: POLYHYDROXYETHYL METHACRYLATE. 2-hydroxyethyl methacrylate : An enoate ester that is the monomethacryloyl derivative of ethylene glycol.		2.0310enoate esterallergen;
polymerisation monomer
nitrofen
nitrofen: structure		1.9710organic molecular entityEC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor;
herbicide
sulfur
Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.		2.110chalcogen;
nonmetal atom		macronutrient
ConditionIndicatedRelationship StrengthStudiesTrials
Birth Weight
The mass or quantity of heaviness of an individual at BIRTH. It is expressed by units of pounds or kilograms.		01.9910
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.8940
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.3820
Abnormalities, Congenital
[description not available]		01.9810
Abnormalities, Drug-Induced
Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.		02.3720
Congenital Limb Deformities
[description not available]		01.9710