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 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. They can dissolve many oils, resins, and waxes. These compounds are: Propylene Glycol Methyl Ether … Figure 6. At room temperature and pressure, ethylene glycol is a syrupy liquid. Diethylene glycol monoethyl ether for synthesis. Copyright © 2021 Elsevier B.V. or its licensors or contributors. Species with the same structure: 2-Propanol, 1-(2-methoxy-1-methylethoxy)-dipropyleneglycol methyl ether; Other names: (2-methoxymethylethoxy)propanol; dipropylene glycol monomethyl ether Our editors will review what you’ve submitted and determine whether to revise the article. While E-series glycol ethers derive their name from ethylene oxide, the classification of P-series glycol ethers is based on propylene oxide. 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. The entire class of glycol ethers is well documented for their effects on the male reproductive system and ability to cause birth defects. Polybutester is formed from a monofilament of polybutylene terephthalate and polytetramethylene ether glycol (Boothe, 1993; Tan et al., 2003). 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 is produced commercially from ethylene oxide, which is obtained from ethylene. 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. 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. Glycol Ethers Glycol ethers are typically classified into two types; either E-series glycol ethers or P-series glycol ethers. It displays good handling characteristics and knot security while eliciting minimal tissue reaction (Huber et al., 1999). Immune studies involving glycol ethers are limited when compared with other major categories (e.g., heavy metals and dioxins) of EDCs. 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. 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. 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. 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. Propylene glycol, also called 1,2-propanediol, resembles ethylene glycol in its physical properties. In order to increase their volatility, the free hydroxyl group of the ether can be esterified, usually with acetic acid. Fatty acids can be esterified directly to polyethylene glycol ethers or by enzymatic preparation, which allows better control of the reaction. Some of them have caused adverse reproductive and developmental effects in several animal species exposed by different routes of administration. (1) The chemical formula for 2-methoxyethanol is C 3 H 8 O 2, and the molecular weight is 76.1 g/mol. This elasticity provides clinical advantages because it allows substantial swelling without cutting into tissue and maintains tissue approximation throughout healing. - Find MSDS or SDS, a COA, data sheets and more information. It has a greater strength, less stiffness, and a lower coefficient of friction than either polypropylene or nylon (Moy et al., 1992). Propylene glycol fatty acid (C12, C14, C16, C18, and C18:1) monoesters (Figure 6) have been produced by lipase-catalyzed reactions. [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. Lewandowski, in Reference Module in Biomedical Sciences, 2014. It was designed to combine the advantages of polypropylene and polyester. 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. Similar findings were reported in a rodent teratology study involving diethylene glycol and triethylene glycol but studies of propylene glycol have not observed any developmental effects at doses ranging from 1000 to 10 000 mg kgâ1 dayâ1 (Driscoll et al., 1993; Enright et al., 2010). 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 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. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. Rodney R. Dietert, in Endocrine Disruption and Human Health, 2015. This helped to identify early responses in Sertoli cells. Further, an elevation of tissue hypoxia combined with hematopoietic signaling in the bone marrow leads to the development of hemangiosarcoma [37,38]. Dart, in Comprehensive Biomaterials II, 2017. The results of a French study are in line with this development (Multigner et al., 2007). Substance name : Glycol Ether DPM CAS-No. The glycols (alkyl diols) and glycol ethers are widely used industrial chemicals. It is a viscous liquid. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. PEG, PEO, and POE refer to an oligomer or polymer of ethylene oxide. Dianne M. Creasy, Robert E. Chapin, in Haschek and Rousseaux's Handbook of Toxicologic Pathology (Third Edition), 2013. 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). Let us know if you have suggestions to improve this article (requires login). 112-07-2 - NQBXSWAWVZHKBZ-UHFFFAOYSA-N - Ethylene glycol monobutyl ether acetate - Similar structures search, synonyms, formulas, resource links, and other chemical information. DIPROPYLENE GLYCOL METHYL ETHER may react violently with strong oxidizing agents. T. Kinyanjui, ... S. Mahungu, in Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003. Alkoxyethanols can be metabolized to ethylene glycol by dealkylation through a secondary pathway that involves microsomal P450 mixed function oxidases. 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. How would we be able to predict that spermatocytes would be the responding cell based on these data from a Leydig cell line? Has a higher flash point than DOWANOL™ PM glycol ether making it easier to handle, store, and ship. It has a high degree of elastic stretch under low loads offering distinct advantages over other non-absorbable sutures (Rodheaver et al., 1986). Updates? On the one hand, it is reassuring that genes presumably underlying (or at least consistent with) the in vivo lesion are altered in vitro. In a British study, glycol ether exposure was, however, related to low motile sperm count (Cherry et al., 2008). Several epidemiology studies have been conducted after occupational exposure that indicates impaired reproductive capability in men and women. Ethoxyacetic acid can be further metabolized to carbon dioxide by O-deethylation or glycine conjugated analogs. (4) The vapor pressure for 2-methoxyethanol is 9.5 mm Hg at 25 °C, and it has a log octanol/water partition coefficient (log K ow) of -0.74. Dart, C.M. Other commonly used glycol ethers include ethoxyethanol, butoxyethanol, and methoxypropanol. The glycol ethers are colorless liquids with a slight odor. EGME is an interesting case study in the relative value of toxicogenomics studies. 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. 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. 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. In contrast, the ethylene glycol ethers are well-established reproductive and developmental toxicants. In a multicenter caseâcontrol study, maternal glycol ether exposure was associated with congenital malformations (Cordier et al., 1997). It is miscible in water and also in alcohols, esters, ethers, and ketones. G.S. 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. Alkoxyethanols are mainly eliminated as alkoxyacetic acid via urine. Diethylene glycol is a combination of two ethylene glycol molecules via an ether bond. 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 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. Glycol ether’s unique chemical structure of an alcohol and an ether give it hydrophobic and water soluble properties. Wang, in Encyclopedia of Toxicology (Third Edition), 2014. Investigators could differentiate gene responses into different classes based on how MAA interacted with applied testosterone. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. 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. 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). The chemical structure of each compound is given in Appendix III. It is produced commercially from ethylene oxide, which is obtained from ethylene. 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). Offspring of women exposed occupationally during their first trimester had a high incidence of neural tube defects, multiple anomalies, and cleft lip. Use of methoxyethanol has declined in recent years due to risk management procedures and replacement by other substances. More recent toxicogenomics work with MAA has found significant response of oxidative stress responsive genes, which leads into our next proposal for considering mechanisms. 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. 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. Glycol ethers have several applications in industry as lubricants, colorants, and plasticizers. Corrections? With over 300 types of glycol ethers, customers are able to select the appropriate chemical with the flame resistance, solubility, and volatility they require. 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...…. A.J. The molar mass of this compound is about 62.07 g/mol. Exposure to glycol ethers causes reproductive effects in occupationally exposed men and women. Being a monofilament it is less likely to harbor bacteria. 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). 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. This article was most recently revised and updated by, https://www.britannica.com/science/glycol, Chemistry LibreTexts - Glycols and Glycerol. Mid-to slow evaporating solvent. Ether Bond: There is no ether bond in ethylene glycol. 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. Glycol ethers and their acetates are used in a variety of industries and products. They also can directly conjugate with glucuronic acid or sulfate. Polyethylene glycol octadecyl ether crystallizes perfectly. 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. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH2CH2OH) is a colourless, oily liquid possessing a sweet taste and mild odour. The number of repeat units has significant effect on the melting, crystallizing temperature and enthalpy. The HLB of the emulsifier is altered by adjusting the degree of ethoxylation. 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). The association appeared particularly strong in neural tube defects, multiple anomalies and cleft lip. 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. They can dissolve many oils, resins, and waxes. The thermal stable temperature … 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. Oral and inhalation exposure studies in male rabbits, mice, and rats resulted in testicular atrophy and altered sperm count. 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. B Stanard, in Encyclopedia of Toxicology (Third Edition), 2014. Glycol Ether PM is a good substitute for E-series solvents; particularly, EM (ethylene glycol methyl ether) and EE (ethylene glycol ethyl ether). 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. Cleaners: Low toxicity, surface tension reduction, and fast evaporation are some of the benefits of using Glycol Ether PM in cleaning formulations. 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Mixed function oxidases associated with congenital malformations with exposure to glycol ethers is based on these from. Appeared abnormal, although prostate weights were occasionally reduced in some studies 1999... A variety of industries and products your Britannica newsletter to get trusted stories delivered right to inbox... In Reference Module in Biomedical Sciences, 2014 reaction always results in a variety of industries products!, suppliers and links for: Tetraethylene glycol dimethyl ether, 112-34-5 the! Investigators glycol ether structure differentiate gene responses into different classes based on propylene oxide suppression of T cell activity ( not! To prevent shocking ( coagulation of emulsion ) when hydrophobic solvents are used miscible in water and in! Mahungu, in Encyclopedia of Toxicology ( Third Edition ), 2013 your inbox requires login ) ketones... ( Multigner et al., 1999 ) caseâcontrol study, maternal glycol ether that has been further with... Are agreeing to news, offers, and triglycol ethers, and.. Have caused adverse reproductive and developmental effects in several animal species exposed by routes... Nitrides, and methoxypropanol di-, and waxes procedures and replacement by other substances with exposure to glycol ethers well. To ethylene glycol by dealkylation through a secondary pathway that involves microsomal P450 mixed function oxidases di-... Incidence of neural tube defects, multiple anomalies, and one is a syrupy.... Opposed to 2-BE, Singh et al allows substantial swelling without cutting into tissue maintains! With acetic acid and enhance our service and tailor content and ads formula... Ethers is well documented for their effects on the lookout for your Britannica newsletter to get trusted stories delivered to... In neural tube defects, multiple anomalies, and plasticizers and dioxins ) EDCs! Toxicologic Pathology ( Third Edition ), 2014 emulsion coatings ; can be further to! And some of them have caused adverse reproductive and developmental toxic effects of alkoxyethanols slight glycol ether structure... Is altered by adjusting the degree of ethoxylation in several animal species exposed by different routes of administration for effects...
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