Men had increased risk of negative effects on sperm count and sperm morphology. 34590-94-8 - WGYZMNBUZFHYRX-UHFFFAOYSA-N - Dipropylene glycol monomethyl ether - Similar structures search, synonyms, formulas, resource links, and other chemical information. Diethylene glycol monoethyl ether for synthesis. 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). Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. More recent toxicogenomics work with MAA has found significant response of oxidative stress responsive genes, which leads into our next proposal for considering mechanisms. PEG, PEO, and POE refer to an oligomer or polymer of ethylene oxide. It is miscible in water and also in alcohols, esters, ethers, and ketones. In order to increase their volatility, the free hydroxyl group of the ether can be esterified, usually with acetic acid. Has a higher flash point than DOWANOL™ PM glycol ether making it easier to handle, store, and ship. DIPROPYLENE GLYCOL METHYL ETHER may react violently with strong oxidizing agents. The HLB of the emulsifier is altered by adjusting the degree of ethoxylation. 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. Methoxyethanol is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. B Stanard, in Encyclopedia of Toxicology (Third Edition), 2014. These compounds are: Propylene Glycol Methyl Ether … It has a high degree of elastic stretch under low loads offering distinct advantages over other non-absorbable sutures (Rodheaver et al., 1986). Structure, properties, spectra, suppliers and links for: Tetraethylene glycol dimethyl ether, 143-24-8. Structure, properties, spectra, suppliers and links for: Diethylene glycol n-butyl ether, 112-34-5. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. 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. In a British study, glycol ether exposure was, however, related to low motile sperm count (Cherry et al., 2008). 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). Oral and inhalation exposure studies in male rabbits, mice, and rats resulted in testicular atrophy and altered sperm count. Ethylene glycol and some of its derivatives are mildly toxic. Propylene glycol is manufactured in large amounts from propylene oxide, which is obtained from propylene. 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. 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. Being a monofilament it is less likely to harbor bacteria. With over 300 types of glycol ethers, customers are able to select the appropriate chemical with the flame resistance, solubility, and volatility they require. Dart, in Comprehensive Biomaterials II, 2017. They are extensively used as solvents in industrial processes and manufacturing and as thinner and viscosity improving agents in coating processes. 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). The Leydig cells never appeared abnormal, although prostate weights were occasionally reduced in some studies. 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. The molar mass of diethylene glycol is 106.12 g/mol. They indicated that past exposure to glycol ethers during the period 1990–2000 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 (2000–2001) did not impact on human semen characteristics. This helped to identify early responses in Sertoli cells. Exposure to glycol ethers causes reproductive effects in occupationally exposed men and women. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH2CH2OH) is a colourless, oily liquid possessing a sweet taste and mild odour. They also can directly conjugate with glucuronic acid or sulfate. Diethylene glycol is a combination of two ethylene glycol molecules via an ether bond. Among the first studies is that of Exon et al. T.A. PE… 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. Corrections? The spectrum of immune alterations detected appeared to be more extensive with 2-ME exposure as opposed to 2-BE exposure. Has 100% water solubility and is ideally suited as a coupling agent in a wide range of solvent systems. 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. Some of them have caused adverse reproductive and developmental effects in several animal species exposed by different routes of administration. 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. Other commonly used glycol ethers include ethoxyethanol, butoxyethanol, and methoxypropanol. Use of methoxyethanol has declined in recent years due to risk management procedures and replacement by other substances. 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. 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. In a multicenter case–control study, maternal glycol ether exposure was associated with congenital malformations (Cordier et al., 1997). 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. 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 Our editors will review what you’ve submitted and determine whether to revise the article. In contrast, the ethylene glycol ethers are well-established reproductive and developmental toxicants. 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. 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). The glycol ethers are colorless liquids with a slight odor. 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. It is a viscous liquid. 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). 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. They can dissolve many oils, resins, and waxes. Glycol ethers have several applications in industry as lubricants, colorants, and plasticizers. Supplier 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. Lewandowski, in Reference Module in Biomedical Sciences, 2014. At room temperature and pressure, ethylene glycol is a syrupy liquid. The results of a French study are in line with this development (Multigner et al., 2007). 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. Dart, C.M. Fatty acid polyglycol esters are good o/w emulsifiers. 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). They are absorbed as volatile fumes from the air by the skin as well as inhalation. Seven of these compounds are ethylene glycol ethers, and one is a propylene glycol ether. EGME is metabolized to methoxyacetic acid, a metabolite that is just as toxic as the parent compound, and which is the active agent used in cell culture studies. G.S. The entire class of glycol ethers is well documented for their effects on the male reproductive system and ability to cause birth defects. 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. Immune studies involving glycol ethers are limited when compared with other major categories (e.g., heavy metals and dioxins) of EDCs. The thermal stable temperature … Polyethylene glycol octadecyl ether crystallizes perfectly. In a study of topical exposure of mice to 2-BE, Singh et al. 112-07-2 - NQBXSWAWVZHKBZ-UHFFFAOYSA-N - Ethylene glycol monobutyl ether acetate - Similar structures search, synonyms, formulas, resource links, and other chemical information. 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. It is produced commercially from ethylene oxide, which is obtained from ethylene. Women exposed have had increased risk of spontaneous abortion and impaired fertility. 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 kg−1 day−1 (Driscoll et al., 1993; Enright et al., 2010). Figure 6. Omissions? 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 crystal structure of C18En for n ≥ 20 is a monoclinic system. Copyright © 2021 Elsevier B.V. or its licensors or contributors. It was designed to combine the advantages of polypropylene and polyester. Propylene glycol, also called 1,2-propanediol, resembles ethylene glycol in its physical properties. Glycol ethers and their acetates are used in a variety of industries and products. 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). Molecular Structure: Ethylene glycol is an individual molecule derived from ethylene oxide. Dianne M. Creasy, Robert E. Chapin, in Haschek and Rousseaux's Handbook of Toxicologic Pathology (Third Edition), 2013. 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. 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. Glycol Ethers Glycol ethers are typically classified into two types; either E-series glycol ethers or P-series glycol ethers. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. Glycol Ether PM is a good substitute for E-series solvents; particularly, EM (ethylene glycol methyl ether) and EE (ethylene glycol ethyl ether). 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. 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. This article was most recently revised and updated by, https://www.britannica.com/science/glycol, Chemistry LibreTexts - Glycols and Glycerol. T. Kinyanjui, ... S. Mahungu, in Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003. While E-series glycol ethers derive their name from ethylene oxide, the classification of P-series glycol ethers is based on propylene oxide. It has a greater strength, less stiffness, and a lower coefficient of friction than either polypropylene or nylon (Moy et al., 1992). 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. 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). Often incorporated into latex emulsion coatings; can be used to prevent shocking (coagulation of emulsion) when hydrophobic solvents are used. 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. Recommended use and restrictions on use Use of the substance/mixture : Solvent 1.3. 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 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. The Glycol Ethers, with Particular Reference to 2-Methoxyethanol and 2-Ethoxyethanol: ... (2EEE), and 1-methoxy-2-propanol or propylene glycol monomethyl ether (IMP). The glycols (alkyl diols) and glycol ethers are widely used industrial chemicals. The glycol ethers were also used as investigative toxicants in the emerging field of male reproductive toxicology in the early 1980s. 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. (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. (1) The chemical formula for 2-methoxyethanol is C 3 H 8 O 2, and the molecular weight is 76.1 g/mol. The term is often applied to the simplest member of the class, ethylene glycol. 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 is produced commercially from ethylene oxide, which is obtained from ethylene. Fatty acids can be esterified directly to polyethylene glycol ethers or by enzymatic preparation, which allows better control of the reaction. The molar mass of this compound is about 62.07 g/mol. Ethylene glycol monobutyl ether for synthesis. Offspring of women exposed occupationally during their first trimester had a high incidence of neural tube defects, multiple anomalies, and cleft lip. Ethoxyacetic acid can be further metabolized to carbon dioxide by O-deethylation or glycine conjugated analogs. Alkoxyethanols are mainly eliminated as alkoxyacetic acid via urine. May initiate the polymerization of isocyanates and epoxides. (4) The chemical formula for 2-ethoxyethanol is C 4 H 10 O 2 The number of repeat units has significant effect on the melting, crystallizing temperature and enthalpy. 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 Substance name : Glycol Ether DPM CAS-No. Further, an elevation of tissue hypoxia combined with hematopoietic signaling in the bone marrow leads to the development of hemangiosarcoma [37,38]. Glycol ether’s unique chemical structure of an alcohol and an ether give it hydrophobic and water soluble properties. Recent epidemiologic studies suggest an association of major congenital malformations with exposure to glycol ethers during the first trimester of pregnancy. We use cookies to help provide and enhance our service and tailor content and ads. Propylene glycol fatty acid (C12, C14, C16, C18, and C18:1) monoesters (Figure 6) have been produced by lipase-catalyzed reactions. The reaction always results in a mixture of mono-, di-, and triglycol ethers, which are then distilled to the required purity. If they catch on fire, toxic gases such as carbon oxides may be produced. 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. 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. They can dissolve many oils, resins, and waxes. Investigators could differentiate gene responses into different classes based on how MAA interacted with applied testosterone. 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. 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 is widely used as antifreeze in automobile cooling systems and in the manufacture of human-made fibres, low-freezing explosives, and brake fluid. It displays good handling characteristics and knot security while eliciting minimal tissue reaction (Huber et al., 1999). Methoxyethanol is an E-series glycol ether derived from methanol and ethylene oxide. Ethylene glycol is a colorless and odorless alcoholic compound having the chemical formula C 2 H 6 O 2. 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 2006 Volume 14 Number 9, 1377-1388. The association appeared particularly strong in neural tube defects, multiple anomalies and cleft lip. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. URL: https://www.sciencedirect.com/science/article/pii/B9780123864543007296, URL: https://www.sciencedirect.com/science/article/pii/B9780702031762000128, URL: https://www.sciencedirect.com/science/article/pii/B9780123820327100724, URL: https://www.sciencedirect.com/science/article/pii/B9780123864543004103, URL: https://www.sciencedirect.com/science/article/pii/B9780124157590000595, URL: https://www.sciencedirect.com/science/article/pii/B9780128011393000144, URL: https://www.sciencedirect.com/science/article/pii/B9780123864543000208, URL: https://www.sciencedirect.com/science/article/pii/B9780128012383000246, URL: https://www.sciencedirect.com/science/article/pii/B012227055X004016, URL: https://www.sciencedirect.com/science/article/pii/B9780128035818101353, Treatment of Infertility with Chinese Medicine (Second Edition), 2013, Encyclopedia of Toxicology (Third Edition), 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), Occupational exposure to chemicals and reproductive health, Reproductive and Developmental Toxicology, Haschek and Rousseaux's Handbook of Toxicologic Pathology (Third Edition), Effects of Endocrine Disrupters on Immune Function and Inflammation, Developmental and Reproductive Toxicology, Encyclopedia of Food Sciences and Nutrition (Second Edition), Fatty acids can be esterified directly to polyethylene, Handbook of Toxicologic Pathology (Second Edition), Fundamentals of Air Pollution (Fourth Edition), Multifunctional Systems for Combined Delivery, Biosensing and Diagnostics. The chemical structure of each compound is given in Appendix III. CAS 111-90-0, chemical formula HOCH₂CH₂OCH₂CH₂OC₂H₅. One of the adverse outcomes following inhalation exposure to 2-BE is an increase in liver hemangiosarcomas in male but not female mice [36]. 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. Ether Bond: There is no ether bond in ethylene glycol. Let us know if you have suggestions to improve this article (requires login). From: Treatment of Infertility with Chinese Medicine (Second Edition), 2013, A. Shafiee, ... H. Nadri, in Encyclopedia of Toxicology (Third Edition), 2014. Cleaners: Low toxicity, surface tension reduction, and fast evaporation are some of the benefits of using Glycol Ether PM in cleaning formulations. 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. Glycol ethers are metabolized to the corresponding aldehyde and alkoxyacetic acid by cytosolic alcohol dehydrogenase (ADH; EC 1.1.1.1) and aldehyde dehydrogenase (ALDH; 1.2.1.3) and further metabolized to ethoxyacetic acid by ALDH, which is thought to be a toxic compound. 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. Updates? Much of this has been further explored with the androgen receptor in the TM3 transformed mouse Leydig cell line.