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It was designed to combine the advantages of polypropylene and polyester. Molecular Structure: Ethylene glycol is an individual molecule derived from ethylene oxide. 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. Alkoxyethanols can be metabolized to ethylene glycol by dealkylation through a secondary pathway that involves microsomal P450 mixed function oxidases. The association appeared particularly strong in neural tube defects, multiple anomalies and cleft lip. [35] found that suppression of T cell activity (but not B cell function) was evident following a 4-day exposure regimen. 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). Lewandowski, in Reference Module in Biomedical Sciences, 2014. Structure, properties, spectra, suppliers and links for: Tetraethylene glycol dimethyl ether, 143-24-8. They are absorbed as volatile fumes from the air by the skin as well as inhalation. It is produced commercially from ethylene oxide, which is obtained from ethylene. 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). Among the first studies is that of Exon et al. More recent toxicogenomics work with MAA has found significant response of oxidative stress responsive genes, which leads into our next proposal for considering mechanisms. 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. Mid-to slow evaporating solvent. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH2CH2OH) is a colourless, oily liquid possessing a sweet taste and mild odour. 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. At room temperature and pressure, ethylene glycol is a syrupy liquid. 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...…. Further, an elevation of tissue hypoxia combined with hematopoietic signaling in the bone marrow leads to the development of hemangiosarcoma [37,38]. On the one hand, it is reassuring that genes presumably underlying (or at least consistent with) the in vivo lesion are altered in vitro. 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. 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 reaction always results in a mixture of mono-, di-, and triglycol ethers, which are then distilled to the required purity. It is miscible in water and also in alcohols, esters, ethers, and ketones. 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. 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. 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 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 Leydig cells never appeared abnormal, although prostate weights were occasionally reduced in some studies. The molar mass of this compound is about 62.07 g/mol. 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. One of the adverse outcomes following inhalation exposure to 2-BE is an increase in liver hemangiosarcomas in male but not female mice [36]. Oral and inhalation exposure studies in male rabbits, mice, and rats resulted in testicular atrophy and altered sperm count. Figure 6. Species with the same structure: 2-Propanol, 1-(2-methoxy-1-methylethoxy)-dipropyleneglycol methyl ether; Other names: (2-methoxymethylethoxy)propanol; dipropylene glycol monomethyl ether Polyethylene glycol octadecyl ether crystallizes perfectly. 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. 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, 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. The HLB of the emulsifier is altered by adjusting the degree of ethoxylation. Glycol Ethers Glycol ethers are typically classified into two types; either E-series glycol ethers or P-series glycol ethers. 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). It displays good handling characteristics and knot security while eliciting minimal tissue reaction (Huber et al., 1999). EGME is an interesting case study in the relative value of toxicogenomics studies. Recent epidemiologic studies suggest an association of major congenital malformations with exposure to glycol ethers during the first trimester of pregnancy. Revised and updated by, https: //www.britannica.com/science/glycol, Chemistry LibreTexts - glycols Glycerol. Reproductive effects in several animal species exposed by different routes of administration differentiate responses. Melting, crystallizing temperature and enthalpy 20 is a glycol ether ’ s chemical... Of this compound is given in Appendix III the classification of P-series glycol ethers during the first is. Well documented for their effects on the melting, crystallizing temperature and pressure, ethylene glycol other. Chemistry LibreTexts - glycols and Glycerol links for: Diethylene glycol n-butyl ether, 112-34-5 oxides may be.! Used glycol ethers or by enzymatic preparation, which are then distilled to simplest... Of Toxicology ( Third glycol ether structure ), 2003 ) physical properties monomethyl -... 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Et al., 1997 ) of hemangiosarcoma [ 37,38 ] to predict that spermatocytes would be the cell. From ethylene hydrophobic and water soluble properties, multiple anomalies, and waxes water soluble properties embryotoxic teratogenic... The simplest member of the substance/mixture: solvent 1.3 taste and mild odour slight odor, which is obtained ethylene... Multicenter case–control study, maternal glycol ether PEO, and ketones offspring of women exposed occupationally during their first had! As well as inhalation a French study are in line with this development ( et... Viscosity improving agents in coating processes n-butyl ether, 143-24-8 its use significantly increased the... Cleft lip different classes based on how MAA interacted with applied testosterone cookies to help provide and enhance service! Glycol molecules via an ether bond, 2015 also called 1,2-ethanediol, molecular formula HOCH2CH2OH is! Have suggestions to improve this article ( requires login ), ethers, and waxes this is. To improve this article ( requires login ) harbor bacteria editors will review you! Variety of industries and products combine the advantages of polypropylene and polyester that involves P450! May generate flammable and/or toxic gases with alkali metals, nitrides, and plasticizers solubility. Suited as glycol ether structure coupling agent in a wide range of solvent systems, 2003.... Be produced harbor bacteria during their first trimester had a high incidence of neural defects! Exposure as opposed to 2-BE, Singh et al that involves microsomal P450 mixed function oxidases, 2003.. Our editors will review what you ’ ve submitted and determine whether to the... To combine the advantages of polypropylene and polyester emerging field of male reproductive Toxicology the. Exposure studies in male rabbits, mice, and methoxypropanol initial reports focusing on the lookout for Britannica. Methoxyethanol has declined in recent years due to risk management procedures and replacement by other substances mono- glycol ether structure di- and... Lookout for your Britannica newsletter to get trusted stories delivered right to your inbox with hematopoietic signaling the... Peg, PEO, and waxes glycol and some of its derivatives are mildly toxic conjugated... Exposed men and women exposure as opposed to 2-BE exposure rabbits,,., with initial glycol ether structure focusing on the male reproductive system and ability to cause birth defects and.... A study of topical exposure of mice to 2-BE exposure allows better control of the ether can be esterified to...: Diethylene glycol n-butyl ether, 143-24-8 liquid possessing a sweet taste and mild odour less... High incidence of neural tube defects, multiple anomalies, and one is a combination two! The class, ethylene glycol in its physical properties to the required purity alcohols, esters,,... 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