Work in the 1980s and 1990s regarding various mechanisms had explored several separate avenues: (1) that MAA could form an MAAâCoA metabolite which could disturb carbohydrate metabolism; (2) that calcium channel blockers and kinase inhibitors could prevent many of the testicular (and other) toxicities observed after EGME treatment; (3) that Sertoli cells were required for the full expression of the cell death program in the spermatocytes; and (4) that kinase activity plays a central role in the spermatocyte death. Glycol ethers are a large group of organic solvents used in industry and the home as glass cleaners, carpet cleaners, floor cleaners and oven cleaners. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. The glycol ethers were also used as investigative toxicants in the emerging field of male reproductive toxicology in the early 1980s. It has embryotoxic and teratogenic effects in the offspring of exposed pregnant women. Studies of propyl and longer-chain (e.g., butyl-, hexyl-) glycol ethers have demonstrated either a lower potency or a complete lack of developmental effects (Tyl et al., 1984; Spencer, 2005). PE… The use of the most toxic glycol ethers has decreased from the mid-1990s and has gradually been replaced with less toxic long chain glycol ethers and propylene glycol ethers. Fatty acid polyglycol esters are good o/w emulsifiers. Rodney R. Dietert, in Endocrine Disruption and Human Health, 2015. The molar mass of this compound is about 62.07 g/mol. Numerous pathogenesis studies identified the early and late pachytene spermatocytes (but not mid pachytene spermatocytes) and the dividing spermatocyte as the most sensitive germ cell for this family of toxicants, with cell death being stage-specific and occurring within 12 hours of a single dose. Structure 2006 Volume 14 Number 9, 1377-1388. Unambiguous epidemiological studies investigating the potential developmental toxicity of these compounds are lacking and thus our knowledge of their developmental effects is based primarily on animal studies. The glycol ethers are colorless liquids with a slight odor. Often incorporated into latex emulsion coatings; can be used to prevent shocking (coagulation of emulsion) when hydrophobic solvents are used. Structure, properties, spectra, suppliers and links for: Tetraethylene glycol dimethyl ether, 143-24-8. Propylene glycol esters of fatty acids, where R1 and R2 represent a fatty acid and/or a hydrogen, and where at least one R represents a fatty acid. It displays good handling characteristics and knot security while eliciting minimal tissue reaction (Huber et al., 1999). This elasticity provides clinical advantages because it allows substantial swelling without cutting into tissue and maintains tissue approximation throughout healing. For example, diethylene glycol dimethylether exposure in pregnant mice produced reduction in fetal body weights and skeletal malformations at 125 mg kgâ1 dayâ1, a dose that did not have systemic effects in the maternal animals (Price et al., 1987). They are extensively used as solvents in industrial processes and manufacturing and as thinner and viscosity improving agents in coating processes. Ethylene glycol is widely used as antifreeze in automobile cooling systems and in the manufacture of human-made fibres, low-freezing explosives, and brake fluid. Recommended use and restrictions on use Use of the substance/mixture : Solvent 1.3. Propylene glycol is manufactured in large amounts from propylene oxide, which is obtained from propylene. They also can directly conjugate with glucuronic acid or sulfate. They can dissolve many oils, resins, and waxes. Glycol ethers have several applications in industry as lubricants, colorants, and plasticizers. Glycol ether’s unique chemical structure of an alcohol and an ether give it hydrophobic and water soluble properties. One of the interesting earlier concepts was an MAA-induced disruption of nuclear receptor signaling, with initial reports focusing on the androgen receptor. May initiate the polymerization of isocyanates and epoxides. T. Kinyanjui, ... S. Mahungu, in Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003. Supplier Several epidemiology studies have been conducted after occupational exposure that indicates impaired reproductive capability in men and women. These compounds are: Propylene Glycol Methyl Ether … The initial materials for the preparation of glycol ethers are ethane oxide (giving ethylene glycol ethers), propane oxide (giving propylene glycol ethers), and alcohols of the desired carbon chain length. Copyright © 2021 Elsevier B.V. or its licensors or contributors. Methoxyethanol is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. Polybutester is formed from a monofilament of polybutylene terephthalate and polytetramethylene ether glycol (Boothe, 1993; Tan et al., 2003). Inhalation, dermal, and oral studies in pregnant rats, rabbits, and mice indicated fetotoxicity with resorption of fetuses and reduced fetal weight, as well as skeletal and cardiovascular abnormalities, increased incidences of major malformations, and minor anomalies. Butoxytriglycol (Triethylene Glycol Monobutyl Ether) C 4 H 9 (OCH 2 CH 2 ) 3 OH The alkoxytriglycols are useful as low-volatility components in paint stripping formulations, as dye carriers for textile dye processes, as chemical process solvents and as intermediates for making esters for use as solvents, surfactants and plasticizers. They indicated that past exposure to glycol ethers during the period 1990â2000 was associated with an increased risk for low sperm concentration, low percentage of rapid progressive motility and morphologically normal sperm below the reference values, but the glycol ethers used at the time of the study (2000â2001) did not impact on human semen characteristics. It is able to stretch to 50% of its original length at a load of 25% of its known breaking point (Rodheaver et al., 1986; Moy et al., 1992). The reaction always results in a mixture of mono-, di-, and triglycol ethers, which are then distilled to the required purity. It is a viscous liquid. EGME is an interesting case study in the relative value of toxicogenomics studies. Exposure to glycol ethers causes reproductive effects in occupationally exposed men and women. Studies of exposed male workers show that glycol ethers can reduce sperm counts and pregnant women exposed to glycol ethers in their work environments are significantly more likely to have children with birth defects such as neural tube defects and cleft lip.157,158, Helena Taskinen, ... Markku Sallmén, in Reproductive and Developmental Toxicology, 2011. : 34590-94-8 Formula : C7H16O3 Synonyms : Dipropylene Glycol Monomethyl Ether, DPM, Dipropylene Glycol Methyl Ether, DPGME BIG no : 13519 1.2. Rodent studies investigating the developmental toxicity of ethylene glycol (EG) have indicated developmental toxicity but only at exceptionally high doses, at or above 1000 mg kgâ1 dayâ1 (ATSDR, 2010). It is produced commercially from ethylene oxide, which is obtained from ethylene. This helped to identify early responses in Sertoli cells. Polybutester is suitable in repair of tissues such as tendons where its elastic properties may be an advantage, particularly in the early phases of healing (Tan et al., 2003). Jane Lyttleton BSc (Hons) (NZ) MPhil (UK) Dip TCM (Aus) Cert Acup (China) Cert Herbal Med (China), in Treatment of Infertility with Chinese Medicine (Second Edition), 2013, Glycol ethers are a large group of organic solvents used in industry and the home as glass cleaners, carpet cleaners, floor cleaners and oven cleaners. Other important glycols include 1,3-butanediol, used as a starting material for the manufacture of brake fluids and of plasticizers for resins; 1,4-butanediol, used in polyurethanes and in polyester resins for coatings and plasticizers, and for making butyrolactone, a valuable solvent and chemical intermediate; 2-ethyl-1,3-hexanediol, an effective insect repellent; and 2-methyl-2-propyl-1,3-propanediol, made into meprobamate, a widely used tranquilizer. There are many studies both in vivo and in vitro that have identified testicular damage and reduced sperm count in several strains of rats and mice. Further, an elevation of tissue hypoxia combined with hematopoietic signaling in the bone marrow leads to the development of hemangiosarcoma [37,38]. Immune studies involving glycol ethers are limited when compared with other major categories (e.g., heavy metals and dioxins) of EDCs. On the one hand, it is reassuring that genes presumably underlying (or at least consistent with) the in vivo lesion are altered in vitro. The Glycol Ethers, with Particular Reference to 2-Methoxyethanol and 2-Ethoxyethanol: ... (2EEE), and 1-methoxy-2-propanol or propylene glycol monomethyl ether (IMP). Unlike ethylene glycol, however, propylene glycol is not toxic and is used extensively in foods, cosmetics, and oral hygiene products as a solvent, preservative, and moisture-retaining agent. Structure, properties, spectra, suppliers and links for: Diethylene glycol n-butyl ether, 112-34-5. DOWANOL™ PPh glycol ether is also used extensively in dyeing applications, where it can function as both a dye solubilizer and as a dye carrier. T.A. Oral and inhalation exposure studies in male rabbits, mice, and rats resulted in testicular atrophy and altered sperm count. They can dissolve many oils, resins, and waxes. They are absorbed as volatile fumes from the air by the skin as well as inhalation. Alkoxyacetic acid is responsible for reproductive and developmental toxic effects of alkoxyethanols. Diethylene glycol is a combination of two ethylene glycol molecules via an ether bond. While E-series glycol ethers derive their name from ethylene oxide, the classification of P-series glycol ethers is based on propylene oxide. Wang, in Encyclopedia of Toxicology (Third Edition), 2014. CAS 111-90-0, chemical formula HOCH₂CH₂OCH₂CH₂OC₂H₅. Ethylene glycol is a colorless and odorless alcoholic compound having the chemical formula C 2 H 6 O 2. 112-07-2 - NQBXSWAWVZHKBZ-UHFFFAOYSA-N - Ethylene glycol monobutyl ether acetate - Similar structures search, synonyms, formulas, resource links, and other chemical information. Propylene glycol monoesters of docosahexaenoic acid and eicosapentaenoic acid that are potentially health-beneficial w/o emulsifiers useful in the food industry have been synthesized by lipase-catalyzed esterification. Vapor-phase triethylene glycol monomethyl ether is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 9.6 hours(SRC), calculated from its rate constant of 4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Ether Bond: There is no ether bond in ethylene glycol. Subsequent work on this and another short-chain fatty acid (valproic acid) found early and specific dysregulation of multiple nuclear receptors through activating the mitogen-activated protein kinase (MAPK) and inhibiting histone deacetylase, although neither were sufficient to account for all the receptor-potentiating effects reported for MAA. It is miscible in water and also in alcohols, esters, ethers, and ketones. Methoxyethanol is an E-series glycol ether derived from methanol and ethylene oxide. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH2CH2OH) is a colourless, oily liquid possessing a sweet taste and mild odour. Corrections? Alkoxyethanols are mainly eliminated as alkoxyacetic acid via urine. The molar mass of diethylene glycol is 106.12 g/mol. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. Ether bond links the two ethylene glycol molecules. In order to increase their volatility, the free hydroxyl group of the ether can be esterified, usually with acetic acid. The chemical structure of each compound is given in Appendix III. Substance name : Glycol Ether DPM CAS-No. Propylene glycol, also called 1,2-propanediol, resembles ethylene glycol in its physical properties. Hampton Research, first in crystallization since 1991, developing and delivering crystallization and optimization screens, reagents, plates, and other tools for the crystallization of biological macromolecules, including proteins (antibody), peptides (insulin), and nucleic acids (DNA). Glycol ethers, with the combination of ether, alcohol and hydrocarbon chain in one molecule, provide versatile solvency characteristics with both polar and non-polar properties. Dioxins ) of EDCs the article, also called 1,2-propanediol, resembles glycol. 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Advantages because it allows substantial swelling without cutting into tissue and maintains tissue approximation throughout healing,!
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