If they catch on fire, toxic gases such as carbon oxides may be produced. How would we be able to predict that spermatocytes would be the responding cell based on these data from a Leydig cell line? At room temperature and pressure, ethylene glycol is a syrupy liquid. They can dissolve many oils, resins, and waxes. 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). Women exposed have had increased risk of spontaneous abortion and impaired fertility. Structure 2006 Volume 14 Number 9, 1377-1388. 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. 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). Other commonly used glycol ethers include ethoxyethanol, butoxyethanol, and methoxypropanol. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. The glycols (alkyl diols) and glycol ethers are widely used industrial chemicals. They also can directly conjugate with glucuronic acid or sulfate. 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. Men had increased risk of negative effects on sperm count and sperm morphology. Supplier This helped to identify early responses in Sertoli cells. Being a monofilament it is less likely to harbor bacteria. Alkoxyethanols are mainly eliminated as alkoxyacetic acid via urine. Exposure to glycol ethers causes reproductive effects in occupationally exposed men and women. We use cookies to help provide and enhance our service and tailor content and ads. 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). Species with the same structure: 2-Propanol, 1-(2-methoxy-1-methylethoxy)-dipropyleneglycol methyl ether; Other names: (2-methoxymethylethoxy)propanol; dipropylene glycol monomethyl ether Seven of these compounds are ethylene glycol ethers, and one is a propylene glycol ether. 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. It is miscible in water and also in alcohols, esters, ethers, and ketones. 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. Immune studies involving glycol ethers are limited when compared with other major categories (e.g., heavy metals and dioxins) of EDCs. 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). While E-series glycol ethers derive their name from ethylene oxide, the classification of P-series glycol ethers is based on propylene oxide. The glycol ethers were also used as investigative toxicants in the emerging field of male reproductive toxicology in the early 1980s. It has a high degree of elastic stretch under low loads offering distinct advantages over other non-absorbable sutures (Rodheaver et al., 1986). Propylene glycol, also called 1,2-propanediol, resembles ethylene glycol in its physical properties. Alkoxyethanols can be metabolized to ethylene glycol by dealkylation through a secondary pathway that involves microsomal P450 mixed function oxidases. Methoxyethanol is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. T.A. Among the first studies is that of Exon et al. Glycol Ethers Glycol ethers are typically classified into two types; either E-series glycol ethers or P-series glycol ethers. Oral and inhalation exposure studies in male rabbits, mice, and rats resulted in testicular atrophy and altered sperm count. 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). Fatty acid polyglycol esters are good o/w emulsifiers. Recent epidemiologic studies suggest an association of major congenital malformations with exposure to glycol ethers during the first trimester of pregnancy. 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. It is produced commercially from ethylene oxide, which is obtained from ethylene. The glycol ethers are colorless liquids with a slight odor. Molecular Structure: Ethylene glycol is an individual molecule derived from ethylene oxide. Investigators could differentiate gene responses into different classes based on how MAA interacted with applied testosterone. The entire class of glycol ethers is well documented for their effects on the male reproductive system and ability to cause birth defects. Ether bond links the two ethylene glycol molecules. It is a viscous liquid. Fatty acids can be esterified directly to polyethylene glycol ethers or by enzymatic preparation, which allows better control of the reaction. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. In those studies where developmental effects were noted, significant maternal toxicity was also observed at or near the dose associated with developmental toxicity, suggesting that EG is at most only slight more toxic to the developing organism than the adult animal. 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 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. EGME is an interesting case study in the relative value of toxicogenomics studies. 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. The crystal structure of C18En for n ≥ 20 is a monoclinic system. Has 100% water solubility and is ideally suited as a coupling agent in a wide range of solvent systems. 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. Further, an elevation of tissue hypoxia combined with hematopoietic signaling in the bone marrow leads to the development of hemangiosarcoma [37,38]. 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. 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). 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. Polyethylene glycol octadecyl ether crystallizes perfectly. A.J. Copyright © 2021 Elsevier B.V. or its licensors or contributors. 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). Offspring of women exposed occupationally during their first trimester had a high incidence of 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. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. 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. Ethylene glycol and some of its derivatives are mildly toxic. 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. Diethylene glycol monoethyl ether for synthesis. 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. The molar mass of this compound is about 62.07 g/mol. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. 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Ethylene glycol monobutyl ether for synthesis. : 34590-94-8 Formula : C7H16O3 Synonyms : Dipropylene Glycol Monomethyl Ether, DPM, Dipropylene Glycol Methyl Ether, DPGME BIG no : 13519 1.2. 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. Structure, properties, spectra, suppliers and links for: Tetraethylene glycol dimethyl ether, 143-24-8. Updates? This elasticity provides clinical advantages because it allows substantial swelling without cutting into tissue and maintains tissue approximation throughout healing. T. Kinyanjui, ... S. Mahungu, in Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003. Ether Bond: There is no ether bond in ethylene glycol. The association appeared particularly strong in neural tube defects, multiple anomalies and cleft lip. PE… [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. With over 300 types of glycol ethers, customers are able to select the appropriate chemical with the flame resistance, solubility, and volatility they require. The spectrum of immune alterations detected appeared to be more extensive with 2-ME exposure as opposed to 2-BE exposure. Dart, in Comprehensive Biomaterials II, 2017. The number of repeat units has significant effect on the melting, crystallizing temperature and enthalpy. Species exposed by different routes of administration 100 % water solubility and is suited! 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