Species with the same structure: 2-Propanol, 1-(2-methoxy-1-methylethoxy)-dipropyleneglycol methyl ether; Other names: (2-methoxymethylethoxy)propanol; dipropylene glycol monomethyl ether Structure, properties, spectra, suppliers and links for: Tetraethylene glycol dimethyl ether, 143-24-8. The glycol ethers are colorless liquids with a slight odor. 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 kg−1 day−1 (ATSDR, 2010). By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. Rodney R. Dietert, in Endocrine Disruption and Human Health, 2015. With over 300 types of glycol ethers, customers are able to select the appropriate chemical with the flame resistance, solubility, and volatility they require. PEG, PEO, and POE refer to an oligomer or polymer of ethylene oxide. 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. Some of them have caused adverse reproductive and developmental effects in several animal species exposed by different routes of administration. Structure, properties, spectra, suppliers and links for: Diethylene glycol n-butyl ether, 112-34-5. Methoxyethanol is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. PE… 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. Organic compound, any of a large class of chemical compounds in which one or more atoms...…, Alcohol, any of a class of organic compounds characterized by one or more hydroxyl (―OH)...…, Molecule, a group of two or more atoms that form the smallest identifiable unit into which...…. They can dissolve many oils, resins, and waxes. formula C6H14O3 14 MW 134.18 14 Class glycol ether MP, ºC -76 14 BP, ºC 196 14 vapor pressure, torr @25ºC 0.126 14 evaporation rate (BuOAc=1) <0.01 34 specific gravity, 25ºC/25ºC 0.988 34 viscosity, cP @ 25ºC 3.85 38 flash point, ºC (closed cup) 93 2 On the other hand, for these to be changed in an unaffected cell type calls into question our ability to predict what the response would be in an animal (human or rodent) after such an exposure. Oral and inhalation exposure studies in male rabbits, mice, and rats resulted in testicular atrophy and altered sperm count. Ethyldiglycol Ethyl di glycol (also known as EDG, 2-(2-ethoxyethoxyethanol, ethoxy diglycol and diethylene glycol monoethylether) is a clear, colourless liquid with a mild, yet characteristic odour. 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. On the one hand, it is reassuring that genes presumably underlying (or at least consistent with) the in vivo lesion are altered in vitro. 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. Ethoxyacetic acid can be further metabolized to carbon dioxide by O-deethylation or glycine conjugated analogs. Figure 6. The fact that such gene sets were upregulated in a transformed line of a cell type which shows no pathology or visible change after EGME exposure in vivo is perplexing. 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. Due to the formation of highly explosive peroxides in the air (not in the solution), they should be protected from heat and other ignition sources. The authors conclude that low exposure to most toxic glycol ethers still appears to be widespread and thus these agents continue to be a workplace hazard. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. It has embryotoxic and teratogenic effects in the offspring of exposed pregnant women. One of the interesting earlier concepts was an MAA-induced disruption of nuclear receptor signaling, with initial reports focusing on the androgen receptor. Glycol Ether PM is a good substitute for E-series solvents; particularly, EM (ethylene glycol methyl ether) and EE (ethylene glycol ethyl ether). Often incorporated into latex emulsion coatings; can be used to prevent shocking (coagulation of emulsion) when hydrophobic solvents are used. 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. 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). They are absorbed as volatile fumes from the air by the skin as well as inhalation. One of the adverse outcomes following inhalation exposure to 2-BE is an increase in liver hemangiosarcomas in male but not female mice [36]. For example, diethylene glycol dimethylether exposure in pregnant mice produced reduction in fetal body weights and skeletal malformations at 125 mg kg−1 day−1, a dose that did not have systemic effects in the maternal animals (Price et al., 1987). These compounds are: Propylene Glycol Methyl Ether … They verified much of the earlier work on the effects of MAA on nuclear receptors, but also reported MAA effects on lipid metabolism, cell death-related genes, cell differentiation, and cell adhesion, inter alia. While E-series glycol ethers derive their name from ethylene oxide, the classification of P-series glycol ethers is based on propylene oxide. Has 100% water solubility and is ideally suited as a coupling agent in a wide range of solvent systems. The Leydig cells never appeared abnormal, although prostate weights were occasionally reduced in some studies. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH2CH2OH) is a colourless, oily liquid possessing a sweet taste and mild odour. 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. Ethylene glycol and some of its derivatives are mildly toxic. Ether Bond: There is no ether bond in ethylene glycol. Dart, in Comprehensive Biomaterials II, 2017. Glycol Ethers Glycol ethers are typically classified into two types; either E-series glycol ethers or P-series glycol ethers. Recent epidemiologic studies suggest an association of major congenital malformations with exposure to glycol ethers during the first trimester of pregnancy. : 34590-94-8 Formula : C7H16O3 Synonyms : Dipropylene Glycol Monomethyl Ether, DPM, Dipropylene Glycol Methyl Ether, DPGME BIG no : 13519 1.2. 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 has a greater strength, less stiffness, and a lower coefficient of friction than either polypropylene or nylon (Moy et al., 1992). The three names are chemically synonymous, but historically PEG is preferred in the biomedical field, whereas PEO is more prevalent in the field of polymer chemistry. Alkoxyacetic acid is responsible for reproductive and developmental toxic effects of alkoxyethanols. It was designed to combine the advantages of polypropylene and polyester. It is miscible in water and also in alcohols, esters, ethers, and ketones. Cleaners: Low toxicity, surface tension reduction, and fast evaporation are some of the benefits of using Glycol Ether PM in cleaning formulations. 34590-94-8 - WGYZMNBUZFHYRX-UHFFFAOYSA-N - Dipropylene glycol monomethyl ether - Similar structures search, synonyms, formulas, resource links, and other chemical information. Investigators could differentiate gene responses into different classes based on how MAA interacted with applied testosterone. The other thing this calls into question is the current common practice of linking gene response data from affected cells to the lesions in those cells. CAS 111-76-2, EC Number 203-905-0, chemical formula C₄H₉OCH₂CH₂OH. Propylene glycol, also called 1,2-propanediol, resembles ethylene glycol in its physical properties. Methoxyethanol is an E-series glycol ether derived from methanol and ethylene oxide. Glycol, any of a class of organic compounds belonging to the alcohol family; in the molecule of a glycol, two hydroxyl (―OH) groups are attached to different carbon atoms. Ethylene glycol is a colorless and odorless alcoholic compound having the chemical formula C 2 H 6 O 2. Chemical structure: This structure is also available as a 2d Mol file or as a computed 3d SD file The 3d structure may be viewed using Java or Javascript. The chemical structure of long hydrocarbon chain resist to solubility in water, while ether or alcohol groups introduce the promoted hydrophilic solubility performance. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. Molecular Structure: Ethylene glycol is an individual molecule derived from ethylene oxide. They are extensively used as solvents in industrial processes and manufacturing and as thinner and viscosity improving agents in coating processes. Copyright © 2021 Elsevier B.V. or its licensors or contributors. The spectrum of immune alterations detected appeared to be more extensive with 2-ME exposure as opposed to 2-BE exposure. In a multicenter case–control study, maternal glycol ether exposure was associated with congenital malformations (Cordier et al., 1997). 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). Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree.... Get a Britannica Premium subscription and gain access to exclusive content. The molar mass of diethylene glycol is 106.12 g/mol. Propylene glycol fatty acid (C12, C14, C16, C18, and C18:1) monoesters (Figure 6) have been produced by lipase-catalyzed reactions. Ethylene glycol monobutyl ether for synthesis. 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 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. It has a high degree of elastic stretch under low loads offering distinct advantages over other non-absorbable sutures (Rodheaver et al., 1986). Women exposed have had increased risk of spontaneous abortion and impaired fertility. Wang, in Encyclopedia of Toxicology (Third Edition), 2014. The Glycol Ethers, with Particular Reference to 2-Methoxyethanol and 2-Ethoxyethanol: ... (2EEE), and 1-methoxy-2-propanol or propylene glycol monomethyl ether (IMP). Being a monofilament it is less likely to harbor bacteria. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. 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