Cleaners: Low toxicity, surface tension reduction, and fast evaporation are some of the benefits of using Glycol Ether PM in cleaning formulations. T. Kinyanjui, ... S. Mahungu, in Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003. 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...…. The glycol ethers were also used as investigative toxicants in the emerging field of male reproductive toxicology in the early 1980s. 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. Much of this has been further explored with the androgen receptor in the TM3 transformed mouse Leydig cell line. The crystal structure of C18En for n ≥ 20 is a monoclinic system. Often incorporated into latex emulsion coatings; can be used to prevent shocking (coagulation of emulsion) when hydrophobic solvents are used. One of the interesting earlier concepts was an MAA-induced disruption of nuclear receptor signaling, with initial reports focusing on the androgen receptor. 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. The Glycol Ethers, with Particular Reference to 2-Methoxyethanol and 2-Ethoxyethanol: ... (2EEE), and 1-methoxy-2-propanol or propylene glycol monomethyl ether (IMP). 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. Propylene glycol fatty acid (C12, C14, C16, C18, and C18:1) monoesters (Figure 6) have been produced by lipase-catalyzed reactions. This article was most recently revised and updated by, https://www.britannica.com/science/glycol, Chemistry LibreTexts - Glycols and Glycerol. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH2CH2OH) is a colourless, oily liquid possessing a sweet taste and mild odour. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. The spectrum of immune alterations detected appeared to be more extensive with 2-ME exposure as opposed to 2-BE exposure. Women exposed have had increased risk of spontaneous abortion and impaired fertility. 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. They also can directly conjugate with glucuronic acid or sulfate. Methoxyethanol is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. [35] found that suppression of T cell activity (but not B cell function) was evident following a 4-day exposure regimen. It is a viscous liquid. It is miscible in water and also in alcohols, esters, ethers, and ketones. Cellosolve was a solvent product containing glycol ethers and registered in the 1920s by Carbide and Carbon Chemicals Corp. Glycol ethers are derived from either ethylene oxide (E-series) or propylene oxide (p-series) combined with an alcohol. Mid-to slow evaporating solvent. Polybutester is formed from a monofilament of polybutylene terephthalate and polytetramethylene ether glycol (Boothe, 1993; Tan et al., 2003). 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. 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). With over 300 types of glycol ethers, customers are able to select the appropriate chemical with the flame resistance, solubility, and volatility they require. aromatic structure, DOWANOL™ PPh glycol ether is an excellent match for phenolic coatings and linings; it is also an excellent coalescent for acrylic-based latexes. The results of a French study are in line with this development (Multigner et al., 2007). Data for these propylene glycol ethers are supplemented with data from three propylene glycol ethers that are closely related to the category members in molecular structure, physicochemical properties and toxicity and thus extend the category. 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. 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. They are absorbed as volatile fumes from the air by the skin as well as inhalation. 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. Diethylene glycol monoethyl ether for synthesis. Fatty acids can be esterified directly to polyethylene glycol ethers or by enzymatic preparation, which allows better control of the reaction. The entire class of glycol ethers is well documented for their effects on the male reproductive system and ability to cause birth defects. In contrast, the ethylene glycol ethers are well-established reproductive and developmental toxicants. PE… 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). At room temperature and pressure, ethylene glycol is a syrupy liquid. The association appeared particularly strong in neural tube defects, multiple anomalies and cleft lip. Ethylene glycol and some of its derivatives are mildly toxic. 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. Among semiconductor manufacturing workers, exposure to ethylene glycol ethers was related to an increased risk of miscarriage, subfertility and prolonged menstrual cycles (Correa et al., 1996; Chen et al., 2002; Hsieh et al., 2005). 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. This helped to identify early responses in Sertoli cells. CAS 111-76-2, EC Number 203-905-0, chemical formula C₄H₉OCH₂CH₂OH. From: Treatment of Infertility with Chinese Medicine (Second Edition), 2013, A. Shafiee, ... H. Nadri, in Encyclopedia of Toxicology (Third Edition), 2014. Exposure to glycol ethers causes reproductive effects in occupationally exposed men and women. 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). How would we be able to predict that spermatocytes would be the responding cell based on these data from a Leydig cell line? 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. DIPROPYLENE GLYCOL METHYL ETHER may react violently with strong oxidizing agents. These compounds are: Propylene Glycol Methyl Ether … 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. The molar mass of this compound is about 62.07 g/mol. Alkoxyethanols are mainly eliminated as alkoxyacetic acid via urine. They can dissolve many oils, resins, and waxes. The reaction always results in a mixture of mono-, di-, and triglycol ethers, which are then distilled to the required purity. 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). Copyright © 2021 Elsevier B.V. or its licensors or contributors. 34590-94-8 - WGYZMNBUZFHYRX-UHFFFAOYSA-N - Dipropylene glycol monomethyl ether - Similar structures search, synonyms, formulas, resource links, and other chemical information. It has a high degree of elastic stretch under low loads offering distinct advantages over other non-absorbable sutures (Rodheaver et al., 1986). By signing up for this email, you are agreeing to news, offers, and information from Encyclopaedia Britannica. 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. Several epidemiology studies have been conducted after occupational exposure that indicates impaired reproductive capability in men and women. 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. This elasticity provides clinical advantages because it allows substantial swelling without cutting into tissue and maintains tissue approximation throughout healing. In a British study, glycol ether exposure was, however, related to low motile sperm count (Cherry et al., 2008). Omissions? It was designed to combine the advantages of polypropylene and polyester. The glycol ethers are colorless liquids with a slight odor. Has a higher flash point than DOWANOL™ PM glycol ether making it easier to handle, store, and ship. Ethylene glycol is a colorless and odorless alcoholic compound having the chemical formula C 2 H 6 O 2. 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). Because different applications require different polymer chain lengths, PEG has tended to refer to oligomers and polymers with a molecular mass below 20,000 g/mol, PEO to polymers with a molecular mass above 20,000 g/mol, and POE to a polymer of any molecular mass. 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. 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. The Leydig cells never appeared abnormal, although prostate weights were occasionally reduced in some studies. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. - Find MSDS or SDS, a COA, data sheets and more information. Numerous follow-on studies have used this compound as a tool, based on that observation and on the assumption of the spermatocyte being the specific target. Substance name : Glycol Ether DPM CAS-No. Other commonly used glycol ethers include ethoxyethanol, butoxyethanol, and methoxypropanol. Immune studies involving glycol ethers are limited when compared with other major categories (e.g., heavy metals and dioxins) of EDCs. This included explorations of the structureâactivity relationships, and many studies using the two most potent congeners (ethylene glycol monomethyl ether [EGME] and ethylene glycol monoethyl ether [EGEE]) as tool compounds to visualize various patterns of response. Methoxyethanol is an E-series glycol ether derived from methanol and ethylene oxide. Updates? They are extensively used as solvents in industrial processes and manufacturing and as thinner and viscosity improving agents in coating processes. Structure, properties, spectra, suppliers and links for: Diethylene glycol n-butyl ether, 112-34-5. Propylene glycol is manufactured in large amounts from propylene oxide, which is obtained from propylene. In a multicenter caseâcontrol study, maternal glycol ether exposure was associated with congenital malformations (Cordier et al., 1997). 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. 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. Ethoxyacetic acid can be further metabolized to carbon dioxide by O-deethylation or glycine conjugated analogs. Exposure to glycol ethers (in particular, 2-methoxyethanol and 2-ethoxyethanol) has been related to reduced semen quality in shipyard painters, metal casters, chemical industry workers and semiconductor industry workers (Figá-Talamanca et al., 2001). Glycol ethers have several applications in industry as lubricants, colorants, and plasticizers. Despite this collective tunnel vision, it is important to remember that several other studies have reported either small vacuoles at the ultrastructural level in Sertoli cells which resolved by 24 hours after a single administration, or early changes in Sertoli cell enzymes or receptors or kinases. [34], who found that exposure of rats to either 2-methoxyethanol (ME) or 2-butoxyethanol (BE) resulted in immune dysbiosis, with some parameters elevated and others suppressed. Although confusing, a possible way to view these data is that they may imply a future where pathway testing is done in any available cell type (or perhaps multiple cell types), and then a yet-to-be-discovered method is applied to identify which cell types will be the ones responding. T.A. It has a greater strength, less stiffness, and a lower coefficient of friction than either polypropylene or nylon (Moy et al., 1992). Glycol ether’s unique chemical structure of an alcohol and an ether give it hydrophobic and water soluble properties. Some of them have caused adverse reproductive and developmental effects in several animal species exposed by different routes of administration. The chemical structure of each compound is given in Appendix III. 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. On the one hand, it is reassuring that genes presumably underlying (or at least consistent with) the in vivo lesion are altered in vitro. PEG, PEO, and POE refer to an oligomer or polymer of ethylene oxide. In order to increase their volatility, the free hydroxyl group of the ether can be esterified, usually with acetic acid. 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. The number of repeat units has significant effect on the melting, crystallizing temperature and enthalpy. Use of methoxyethanol has declined in recent years due to risk management procedures and replacement by other substances. Figure 6. A.J. A current model of 2-BE effects seen in mice suggests that 2-BE induces macrophage activation and inflammation in the liver involving Kupffer cells (liver macrophages). Animal studies have reported testicular damage, reduced fertility, early embryonic death, birth defects, and delayed development from inhalation and oral exposure to the glycol ethers.156 Occupational exposure to glycol ethers has also been shown to result in reproductive and developmental impacts in humans. By continuing you agree to the use of cookies. 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