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Triethylene Glycol
"Descrizione"
by A_Partyns (12876 pt)
2023-Sep-11 19:57

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

References_______________________________________________________________________

(1) Kaushik MK, Kaul SC, Wadhwa R, Yanagisawa M, Urade Y.  Triethylene glycol, an active component of Ashwagandha (Withania somnifera) leaves, is responsible for sleep induction.
PLoS One. 2017 Feb 16;12(2):e0172508. doi: 10.1371/journal.pone.0172508. 

(2) Sadeghinejad L, Cvitkovitch DG, Siqueira WL, Santerre JP, Finer Y. Triethylene Glycol Up-Regulates Virulence-Associated Genes and Proteins in Streptococcus mutans. PLoS One. 2016 Nov 7;11(11):e0165760. doi: 10.1371/journal.pone.0165760. 

(3) 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. 

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