Kwon D, Lim YM, Kwon JT, Shim I, Kim E, Lee DH, Yoon BI, Kim P, Kim HM. Evaluation of pulmonary toxicity of benzalkonium chloride and triethylene glycol mixtures using in vitro and in vivo systems. Environ Toxicol. 2019 May;34(5):561-572. doi: 10.1002/tox.22722. 

Triller T, Sommermann D, Schraml M, Sommer F, Lapeira E, Bou-Ali MM, Köhler W. The Soret effect in ternary mixtures of water+ethanol+triethylene glycol of equal mass fractions: Ground and microgravity experiments. Eur Phys J E Soft Matter. 2019 Mar 7;42(3):27. doi: 10.1140/epje/i2019-11789-7. 

Abstract. Measurements of the Soret and thermodiffusion coefficients of a symmetric ternary mixture with equal mass fractions of water, ethanol, and triethylene glycol have been performed by two-color optical beam deflection (2-OBD) and the thermogravitational column technique (TGC) in the laboratory and under microgravity conditions in the Selectable Optical Diagnostics Instrument (SODI) aboard the International Space Station. The results from all three experimental techniques agree within the experimental error bars, which result mainly from the inversion of the contrast factor matrices. TGC shows by far the lowest, 2-OBD the highest error amplification. The microgravity measurements are in between. The agreement with the microgravity results shows that thermosolutal convection could be well controlled in the 2-OBD experiments by a proper orientation of the temperature gradient. Despite the different condition numbers, the results are invariant under the choice of the independent compositions. Based on the orientation of the confidence ellipsoid in the ternary composition diagram, not all coefficients are equally affected by experimental errors. Although there are appreciable uncertainties for water and ethanol, the Soret and the thermodiffusion coefficients of triethylene glycol could be obtained with a good accuracy due to the favorable orientation of the confidence ellipsoid. We have found that water behaves thermophobic, corresponding to a positive Soret coefficient, whereas both ethanol and triethylene glycol are thermophilic with negative Soret coefficients. This resembles the behaviour of the binary system ethanol/water above the ethanol concentration of the sign change.

Sb H, X J, Qh Y, Xr Z, Bb Z, Kh W, Xy S, Yt C, Xr R, Jf M, G W, Yh P. The vicious circle between mitochondrial oxidative stress and dynamic abnormality mediates triethylene glycol dimethacrylate-induced preodontoblast apoptosis. Free Radic Biol Med. 2019 Apr;134:644-656. doi: 10.1016/j.freeradbiomed.2019.02.013.

Kim IS, Park HC, Quan H, Kim Y, Wu L, Yang HC. Effects of triethylene glycol dimethacrylate and hydroxyethyl methacrylate on macrophage polarization. Int Endod J. 2019 Jul;52(7):987-998. doi: 10.1111/iej.13088. Epub 2019 Feb 20. PMID: 30703248.

Oh E, Garg S, Liu Y, Afzal S, Gao R, Yun CO, Kaul SC, Wadhwa R. Identification and Functional Characterization of Anti-metastasis and Anti-angiogenic Activities of Triethylene Glycol Derivatives. Front Oncol. 2018 Nov 28;8:552. doi: 10.3389/fonc.2018.00552. 

Abstract. We had previously reported anticancer activity in the water extract (WEX) of Ashwagandha leaves, and identified Triethylene glycol (TEG) as an active tumor suppressor component. In this study, we investigated anti-migratory and anti-angiogenesis activities of WEX and TEG. We conducted in vitro and in vivo experiments using TEG, and its two derivatives, Triethyleneglycol dimethacrylate (TD-10), and Tetraethyleneglycol dimethacrylate (TD-11). The data revealed strong anticancer and anti-metastasis potentials in the derivatives. Non-toxic, anti-migratory doses of the derivatives showed inhibition of canonical Wnt/β-catenin axis and consequent downregulation of EMT-signaling proteins (Vimentin, MMPs and VEGF). These results endorse that the TD-10 and TD-11 have potential to safely put a check on the aggressiveness of the metastatic cells and therefore represent promising candidates for the treatment of metastatic cancers.

Schertl P, Volk J, Perduns R, Adam K, Leyhausen G, Bakopoulou A, Geurtsen W. Impaired angiogenic differentiation of dental pulp stem cells during exposure to the resinous monomer triethylene glycol dimethacrylate. Dent Mater. 2019 Jan;35(1):144-155. doi: 10.1016/j.dental.2018.11.006.

Nilsen BW, Simon-Santamaria J, Örtengren U, Jensen E, Bruun JA, Michelsen VB, Sørensen KK. Dose- and time-dependent effects of triethylene glycol dimethacrylate on the proteome of human THP-1 monocytes. Eur J Oral Sci. 2018 Oct;126(5):345-358. doi: 10.1111/eos.12559. 

Mikulás K, Hermann P, Gera I, Komlódi T, Horváth G, Ambrus A, Tretter L. Triethylene glycol dimethacrylate impairs bioenergetic functions and induces oxidative stress in mitochondria via inhibiting respiratory Complex I. Dent Mater. 2018 Jul;34(7):e166-e181. doi: 10.1016/j.dental.2018.03.012. 

Torun D, Torun ZÖ, Demirkaya K, Sarper M, Elçi MP, Avcu F. Microarray analysis of the gene expression profile in triethylene glycol dimethacrylate-treated human dental pulp cells. Niger J Clin Pract. 2017 Nov;20(11):1368-1403. doi: 10.4103/1119-3077.181353. 

Abstract. Objective: Triethylene glycol dimethacrylate (TEGDMA) is an important resin monomer commonly used in the structure of dental restorative materials. Recent studies have shown that unpolymerized resin monomers may be released into the oral environment and cause harmful biological effects. We investigated changes in the gene expression profiles of TEGDMA-treated human dental pulp cells (hDPCs) following short- (1-day) and long-term (7-days) exposure....Conclusions: Our results suggest that TEGDMA can change the many functions of hDPCs through large changes in gene expression levels and complex interactions with different signaling pathways.

Alizadehgharib S, Östberg AK, Dahlgren U. Triethylene glycol dimethacrylate: adjuvant properties and effect on cytokine production. Acta Biomater Odontol Scand. 2017 Dec 5;4(1):1-9. doi: 10.1080/23337931.2017.1409075.

Abstract. Objective: Leakage of monomers from dental fillings due to incomplete curing is very common. The objective of the present study was to examine the cytokine profile in cells exposed to triethyleneglycol dimethacrylate (TEGDMA) and the adjuvant properties of TEGDMA. Materials and methods: Human peripheral blood mononuclear cells were exposed to TEGDMA (500 and 1000 μM) for 24 h in vitro. Bio-Plex Pro™ assays were used for analysis and detection of cytokines. In vivo, BALB/c mice were immunized subcutaneously in the base of the tail with TEGDMA in combination with ovalbumin (OVA). Results: The cytokine levels of IL-8, IL-18, GRO-α and MCP-1 were significantly increased for both concentrations. IL-1β, IL-6 and TNF-α was only significantly increased in cultures exposed to 500 μM TEGDMA. The concentration of TNF-α was significantly decreased in cultures exposed to 1000 μM TEGDMA. Animals immunized with OVA co-administrated with TEGDMA had a significantly higher IgE and IgG anti-OVA antibody levels in blood than animals immunized with OVA only. Conclusions: TEGDMA affects production of proinflammatory cytokines IL-1β, IL-6, IL-8, IL-18 and TNF-α. This inflammatogenic capacity renders TEGDMAs adjuvant properties, which may interfere with the homeostasis between the immune system and the indigenous microflora in the oral cavity.

Öncel Torun Z, Torun D, Baykal B, Öztuna A, Yeşildal F, Avcu F. Effects of triethylene glycol dimethacrylate (TEGDMA) on the odontoclastic differentiation ability of human dental pulp cells. J Appl Oral Sci. 2017 Nov-Dec;25(6):631-640. doi: 10.1590/1678-7757-2016-0626. 

 Abstract. Objectives: The primary purpose of this study was to examine the effects of triethylene glycol dimethacrylate (TEGDMA) on odontoclastic differentiation in the dental pulp tissue....Results: TEGDMA caused relatively less odontoclastic differentiation in comparison with the control group; however, odontoclastic differentiation augmented with increasing doses of TEGDMA (p<0.05). The mRNA and protein expression of OPG was lower in TEGDMA treated pulp cells than in the control group (p<0.05). While the mRNA expression of RANKL remained unchanged compared to the control group (p>0.05), its protein expression was higher than the control group (p<0.05). In addition, TEGDMA increased the apoptosis of dental pulp cells dose dependently. Conclusions: TEGDMA reduced the odontoclastic differentiation ability of human dental pulp cells. However, odontoclastic differentiation ratios increased proportionally with the increasing dose of TEGDMA.

Triethylene Glycol is a chemical compound, an ethylene polyglycol.

The name describes the structure of the molecule

• "Tri" indicates the presence of three units of a particular component.
• "Ethylene" refers to ethylene, an unsaturated aliphatic hydrocarbon.
• "Glycol" indicates that the molecule belongs to the class of diols, which are alcohols with two -OH functional groups.

Description of raw materials used in production

• Ethylene. An unsaturated hydrocarbon serving as the starting point for the production of ethylene oxide.
• Oxygen. Used in producing ethylene oxide via the oxidation of ethylene.
• Glycol. A family of alcohols containing two -OH groups per molecule; essential for producing TEG from ethylene.

Detailed summary of the production process.

• Production of Ethylene Oxide. Ethylene is reacted with oxygen in the presence of a silver catalyst to produce ethylene oxide.
• Hydration of Ethylene Oxide. Ethylene oxide is hydrated to produce monoethylene glycol (MEG).
• Conversion to Diethylene Glycol and Triethylene Glycol. Some of the produced MEG is further reacted with ethylene oxide to yield diethylene glycol (DEG). Some of the DEG is then reacted with more ethylene oxide to form TEG.
• Purification. TEG is separated from by-products through distillation.

What it is for and where

Medical Applications

Disinfection. Triethylene Glycol has antibacterial properties and is utilized in some products as a disinfectant.

Pharmaceutical Formulations. It can be used as a component in some pharmaceutical formulations.

Cosmetics

• Fragrance. It plays a very important role in the formulation of cosmetic products as it provides the possibility of enhancing, masking or adding fragrance to the final product, increasing its marketability. It is able to create a perceptible pleasant odour, masking a bad smell. The consumer always expects to find a pleasant or distinctive scent in a cosmetic product. 
• Viscosity control agent. It controls and adapts, Increasing or decreasing, viscosity to the required level for optimal chemical and physical stability of the product and dosage in gels, suspensions, emulsions, solutions. 
• Perfuming. Unlike fragrance, which can also contain slightly less pleasant or characteristic odours, the term perfume indicates only very pleasant fragrances. Used for perfumes and aromatic raw materials.

Commercial Applications

Plastics and Resins. TEG is used as a plasticizer in resins and plastics.

Ink and Dye Production. It serves as a solvent for inks, paints, and dyes.

Dehumidification. TEG is commonly utilized in the dehumidification processes of natural gas and other gases.

Adhesive Production. Acts as a solvent in various adhesives.

Some studies on Triethylene glycol dimethacrylate

Insomnia is the most common sleep complaint which occurs due to difficulty in falling asleep or maintaining it. Most of currently available drugs for insomnia develop dependency and/or adverse effects. Hence natural therapies could be an alternative choice of treatment for insomnia. The root or whole plant extract of Ashwagandha (Withania somnifera) has been used to induce sleep in Indian system of traditional home medicine, Ayurveda. However, its active somnogenic components remain unidentified. Authors investigated the effect of various components of Ashwagandha leaf on sleep regulation by oral administration in mice. It was found that the alcoholic extract that contained high amount of active withanolides was ineffective to induce sleep in mice. However, the water extract which contain triethylene glycol as a major component induced significant amount of non-rapid eye movement sleep with slight change in rapid eye movement sleep. Commercially available triethylene glycol also increased non-rapid eye movement sleep in mice in a dose-dependent (10–30 mg/mouse) manner. These results clearly demonstrated that triethylene glycol is an active sleep-inducing component of Ashwagandha leaves and could potentially be useful for insomnia therapy (1).

Triethylene glycol dimethacrylate (TEGDMA) is a diluent monomer used pervasively in dental composite resins. Through hydrolytic degradation of the composites in the oral cavity it yields a hydrophilic biodegradation product, triethylene glycol (TEG), which has been shown to promote the growth of Streptococcus mutans, a dominant cariogenic bacterium. Previously it was shown that TEG up-regulated gtfB, an important gene contributing to polysaccharide synthesis function in biofilms. However, molecular mechanisms related to TEG's effect on bacterial function remained poorly understood. In the present study, S. mutans UA159 was incubated with clinically relevant concentrations of TEG at pH 5.5 and 7.0. Quantitative real-time PCR, proteomics analysis, and glucosyltransferase enzyme (GTF) activity measurements were employed to identify the bacterial phenotypic response to TEG. A S. mutans vicK isogenic mutant (SMΔvicK1) and its associated complemented strain (SMΔvicK1C), an important regulatory gene for biofilm-associated genes, were used to determine if this signaling pathway was involved in modulation of the S. mutans virulence-associated genes. Extracted proteins from S. mutans biofilms grown in the presence and absence of TEG were subjected to mass spectrometry for protein identification, characterization and quantification. TEG up-regulated gtfB/C, gbpB, comC, comD and comE more significantly in biofilms at cariogenic pH (5.5) and defined concentrations. Differential response of the vicK knock-out (SMΔvicK1) and complemented strains (SMΔvicK1C) implicated this signalling pathway in TEG-modulated cellular responses. TEG resulted in increased GTF enzyme activity, responsible for synthesizing insoluble glucans involved in the formation of cariogenic biofilms. As well, TEG increased protein abundance related to biofilm formation, carbohydrate transport, acid tolerance, and stress-response. Proteomics data was consistent with gene expression findings for the selected genes. These findings demonstrate a mechanistic pathway by which TEG derived from commercial resin materials in the oral cavity promote S. mutans pathogenicity, which is typically associated with secondary caries (2)

Dental pulp stem cells (DPSCs) can differentiate into tissue specific lineages to support dental pulp regeneration after injuries. Triethylene glycol dimethacrylate (TEGDMA) is a widely used co-monomer in restorative dentistry with adverse effects on cellular metabolism. Aim of this study was to analyze the impact of TEGDMA on the angiogenic differentiation potential of DPSCs. The results of the present study show that TEGDMA concentration dependently impair the angiogenic differentiation potential of DPSCs and may affect wound healing and the formation of granulation tissue (3).

Triethylene glycol dimethacrylate studies

• 
  Molecular Formula  C₆H₁₄O₄ or HOCH₂(CH₂CH₂O)₂CH₂OH
• Molecular Weight  150.174 g/mol
• CAS  112-27-6   
• EC number   203-953-2

• Trigen
• Triglycol
• 2,2'-Ethylenedioxydiethanol
• 1,2-Bis(2-hydroxyethoxy)ethane
• Triethyleneglycol
• Ethylene glycol dihydroxydiethyl ether
• EINECS 203-953-2