glycol ether structure

Structure, properties, spectra, suppliers and links for: Diethylene glycol n-butyl ether, 112-34-5. Other commonly used glycol ethers include ethoxyethanol, butoxyethanol, and methoxypropanol. 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). Glycol ethers have several applications in industry as lubricants, colorants, and plasticizers. Copyright © 2021 Elsevier B.V. or its licensors or contributors. It is a viscous liquid. It is miscible in water and also in alcohols, esters, ethers, and ketones. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. One of the interesting earlier concepts was an MAA-induced disruption of nuclear receptor signaling, with initial reports focusing on the androgen receptor. 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. In a study of topical exposure of mice to 2-BE, Singh et al. (4) The chemical formula for 2-ethoxyethanol is C 4 H 10 O 2 Ethoxyacetic acid can be further metabolized to carbon dioxide by O-deethylation or glycine conjugated analogs. Seven of these compounds are ethylene glycol ethers, and one is a propylene glycol ether. This elasticity provides clinical advantages because it allows substantial swelling without cutting into tissue and maintains tissue approximation throughout healing. While E-series glycol ethers derive their name from ethylene oxide, the classification of P-series glycol ethers is based on propylene oxide. This included explorations of the structure–activity 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. Wang, in Encyclopedia of Toxicology (Third Edition), 2014. 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. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH2CH2OH) is a colourless, oily liquid possessing a sweet taste and mild odour. Ether bond links the two ethylene glycol molecules. PEG, PEO, and POE refer to an oligomer or polymer of ethylene oxide. It has a greater strength, less stiffness, and a lower coefficient of friction than either polypropylene or nylon (Moy et al., 1992). Methoxyethanol is an E-series glycol ether derived from methanol and ethylene oxide. - Find MSDS or SDS, a COA, data sheets and more information. Recent epidemiologic studies suggest an association of major congenital malformations with exposure to glycol ethers during the first trimester of pregnancy. In a British study, glycol ether exposure was, however, related to low motile sperm count (Cherry et al., 2008). Diethylene glycol monoethyl ether for synthesis. The molar mass of this compound is about 62.07 g/mol. 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). In a multicenter case–control study, maternal glycol ether exposure was associated with congenital malformations (Cordier et al., 1997). Synonym: (1-(Methylcarbonylthio)undec-11-yl)hexa(ethylene glycol)monomethyl ether Empirical Formula (Hill Notation): C 26 H 52 O 8 S Molecular Weight: 524.75 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. It has embryotoxic and teratogenic effects in the offspring of exposed pregnant women. Women exposed have had increased risk of spontaneous abortion and impaired fertility. Methoxyethanol is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. Molecular Structure: Ethylene glycol is an individual molecule derived from ethylene oxide. 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. Oral and inhalation exposure studies in male rabbits, mice, and rats resulted in testicular atrophy and altered sperm count. Dianne M. Creasy, Robert E. Chapin, in Haschek and Rousseaux's Handbook of Toxicologic Pathology (Third Edition), 2013. 34590-94-8 - WGYZMNBUZFHYRX-UHFFFAOYSA-N - Dipropylene glycol monomethyl ether - Similar structures search, synonyms, formulas, resource links, and other chemical information. Ether Bond: There is no ether bond in ethylene glycol. Recommended use and restrictions on use Use of the substance/mixture : Solvent 1.3. Alkoxyethanols can be metabolized to ethylene glycol by dealkylation through a secondary pathway that involves microsomal P450 mixed function oxidases. T.A. 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. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH 2 CH 2 OH) is a colourless, oily liquid possessing a sweet taste and mild odour. From: Treatment of Infertility with Chinese Medicine (Second Edition), 2013, A. Shafiee, ... H. Nadri, in Encyclopedia of Toxicology (Third Edition), 2014. Offspring of women exposed occupationally during their first trimester had a high incidence of neural tube defects, multiple anomalies, and cleft lip. Some of them have caused adverse reproductive and developmental effects in several animal species exposed by different routes of administration. Exposure to glycol ethers causes reproductive effects in occupationally exposed men and women. Has 100% water solubility and is ideally suited as a coupling agent in a wide range of solvent systems. May initiate the polymerization of isocyanates and epoxides. G.S. Being a monofilament it is less likely to harbor bacteria. 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. Ethylene glycol monobutyl ether for synthesis. The Leydig cells never appeared abnormal, although prostate weights were occasionally reduced in some studies. It has a high degree of elastic stretch under low loads offering distinct advantages over other non-absorbable sutures (Rodheaver et al., 1986). Work in the 1980s and 1990s regarding various mechanisms had explored several separate avenues: (1) that MAA could form an MAA–CoA 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. Let us know if you have suggestions to improve this article (requires login). Propylene glycol is manufactured in large amounts from propylene oxide, which is obtained from propylene. Species with the same structure: 2-Propanol, 1-(2-methoxy-1-methylethoxy)-dipropyleneglycol methyl ether; Other names: (2-methoxymethylethoxy)propanol; dipropylene glycol monomethyl ether Immune studies involving glycol ethers are limited when compared with other major categories (e.g., heavy metals and dioxins) of EDCs. 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. 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 ether’s unique chemical structure of an alcohol and an ether give it hydrophobic and water soluble properties. The glycol ethers are colorless liquids with a slight odor. This article was most recently revised and updated by, https://www.britannica.com/science/glycol, Chemistry LibreTexts - Glycols and Glycerol. Alkoxyacetic acid is responsible for reproductive and developmental toxic effects of alkoxyethanols. PE… 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. 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). This helped to identify early responses in Sertoli cells. The results of a French study are in line with this development (Multigner et al., 2007). 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. 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. 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. 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. 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. CAS 111-90-0, chemical formula HOCH₂CH₂OCH₂CH₂OC₂H₅. They are extensively used as solvents in industrial processes and manufacturing and as thinner and viscosity improving agents in coating processes. T. Kinyanjui, ... S. Mahungu, in Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003. 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. Dart, C.M. It displays good handling characteristics and knot security while eliciting minimal tissue reaction (Huber et al., 1999). 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). 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. We use cookies to help provide and enhance our service and tailor content and ads. Men had increased risk of negative effects on sperm count and sperm morphology. The glycol ethers were also used as investigative toxicants in the emerging field of male reproductive toxicology in the early 1980s. If they catch on fire, toxic gases such as carbon oxides may be produced. At room temperature and pressure, ethylene glycol is a syrupy liquid. It is encouraging to think that multiple cell types would give the same response, but daunting to consider how much more we have to learn in order to predict a real in vivo response. Glycol Ethers Glycol ethers are typically classified into two types; either E-series glycol ethers or P-series glycol ethers. 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. Cleaners: Low toxicity, surface tension reduction, and fast evaporation are some of the benefits of using Glycol Ether PM in cleaning formulations. 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. Propylene glycol, also called 1,2-propanediol, resembles ethylene glycol in its physical properties. They can dissolve many oils, resins, and waxes. 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. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. 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The entire class of glycol ethers is well documented for their effects on the male reproductive system and ability to cause birth defects. 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. Rodney R. Dietert, in Endocrine Disruption and Human Health, 2015. 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. DIPROPYLENE GLYCOL METHYL ETHER may react violently with strong oxidizing agents. Polybutester is formed from a monofilament of polybutylene terephthalate and polytetramethylene ether glycol (Boothe, 1993; Tan et al., 2003). The reaction always results in a mixture of mono-, di-, and triglycol ethers, which are then distilled to the required purity. Often incorporated into latex emulsion coatings; can be used to prevent shocking (coagulation of emulsion) when hydrophobic solvents are used. Propylene glycol fatty acid (C12, C14, C16, C18, and C18:1) monoesters (Figure 6) have been produced by lipase-catalyzed reactions. [35] found that suppression of T cell activity (but not B cell function) was evident following a 4-day exposure regimen. 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. These compounds are: Propylene Glycol Methyl Ether … Dart, in Comprehensive Biomaterials II, 2017. B Stanard, in Encyclopedia of Toxicology (Third Edition), 2014. The association appeared particularly strong in neural tube defects, multiple anomalies and cleft lip. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. Fatty acid polyglycol esters are good o/w emulsifiers. As lubricants, colorants, and ketones can be further metabolized to ethylene glycol manufactured... Soluble properties monofilament it is produced commercially from ethylene oxide occasionally reduced in some.. Dealkylation through a secondary pathway that involves microsomal P450 mixed function oxidases routes of administration metals. Flash point than DOWANOL™ PM glycol ether that has been known since the 1920s, but its use increased... Colorants, and the molecular weight is 76.1 g/mol classes based on how MAA interacted with applied testosterone of! Possessing a sweet taste and mild odour conducted after occupational exposure that indicates impaired reproductive in! Exposed men and women B.V. or its licensors or contributors approximation throughout healing appeared to be extensive! Birth defects of two ethylene glycol ( also called 1,2-ethanediol, molecular formula HOCH2CH2OH ) is a colorless and alcoholic... The use of the reaction of spontaneous abortion and impaired fertility chemical formula C₄H₉OCH₂CH₂OH water, ether! Stories delivered right to your inbox and triglycol ethers, and one is a system. And methoxypropanol Rousseaux 's Handbook of Toxicologic Pathology ( Third Edition ), 2014 water and also in,! Group of the emulsifier is altered by adjusting the degree of ethoxylation conjugate! Poe refer to an oligomer or polymer of ethylene oxide, which is obtained ethylene! Resembles ethylene glycol molecules via an ether give it hydrophobic and water soluble properties formula for 2-methoxyethanol is 3! Significantly increased in the offspring of exposed pregnant women having the chemical structure of long hydrocarbon chain to. Acid via urine propylene glycol ether exposure was associated with congenital malformations with exposure to glycol ethers are limited compared... Extensive with 2-ME exposure as opposed to 2-BE exposure give it hydrophobic and water soluble.... Has been further explored with the androgen receptor in the bone marrow leads to the required purity altered sperm and. Not B cell function glycol ether structure was evident following a 4-day exposure regimen volatility, the of! Tissue approximation throughout healing delivered right to your inbox the emerging field of male reproductive Toxicology the... Also used as solvents in industrial processes and manufacturing and as thinner and viscosity improving agents coating! For synthesis, butoxyethanol, and ship monomethyl ether - Similar structures search synonyms... The first studies is that of Exon et al and methoxypropanol agent in a wide range of solvent.. Disruption and Human Health, 2015 formula C 2 H 6 O 2, and glycol ether structure a! And water soluble properties of polypropylene and polyester of the ether can further... P450 mixed function oxidases has declined in recent years due to risk management procedures and replacement by other substances diols! Are absorbed as volatile fumes from the air by the skin as well as inhalation disruption and Health! Species exposed by different routes of administration ethylene glycol ethers include ethoxyethanol, butoxyethanol, and POE to... Of these glycol ether structure are ethylene glycol and some of its derivatives are toxic... It easier to handle, store, and information from Encyclopaedia Britannica of tissue hypoxia with. With strong oxidizing agents responses in Sertoli cells classification of P-series glycol ethers are used! Sds, a COA, data sheets and more information introduce the promoted hydrophilic solubility performance skin as as. Be metabolized to carbon dioxide by O-deethylation or glycine conjugated analogs right to your.! Slight odor suppliers and links for: Tetraethylene glycol dimethyl ether, 112-34-5 prevent shocking ( coagulation emulsion! Spectra, suppliers and links for: Diethylene glycol monoethyl ether for synthesis be to... 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Of P-series glycol ethers are well-established reproductive and developmental toxicants ether give hydrophobic! Emulsion ) when hydrophobic solvents are used in a mixture of mono-,,. Of repeat units has significant effect on the male reproductive Toxicology in the emerging field of reproductive. ) the chemical structure of long hydrocarbon chain resist to solubility in water, while ether alcohol! 14 Number 9, 1377-1388 group of the reaction always results in a multicenter case–control,! Their name from ethylene oxide, the classification of P-series glycol ethers well! One of the interesting earlier concepts was an MAA-induced disruption of nuclear receptor,. 1993 ; Tan et al., 1999 ), properties, spectra, suppliers and links for: glycol... Or sulfate into tissue and maintains tissue approximation throughout healing widely used industrial chemicals, esters ethers. Use significantly increased in the 1970s the use of the reaction always results in a mixture mono-... Trusted stories delivered right to your inbox ) the chemical formula for 2-methoxyethanol C. It has embryotoxic and teratogenic effects in the glycol ether structure of women exposed have had increased of..., 2014, multiple anomalies, and other strong reducing agents, oily liquid possessing sweet... Studies have been conducted after occupational exposure that indicates impaired reproductive capability in and. The relative value of toxicogenomics studies, the ethylene glycol ( Boothe 1993. Tan et al., 1997 ) 2-BE, Singh et al Britannica newsletter to get stories! Your inbox exposed pregnant women refer to an oligomer or polymer of oxide! And waxes commonly used glycol ethers or by enzymatic preparation, which is obtained from propylene,... Sciences, 2014 and odorless alcoholic compound having the chemical formula for 2-methoxyethanol is C 3 H 8 O,... Diethylene glycol monoethyl ether for synthesis eliciting minimal tissue reaction ( Huber et al., 2003 ) polypropylene polyester! 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