May initiate the polymerization of isocyanates and epoxides. 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. Omissions? 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 Ether PM is a good substitute for E-series solvents; particularly, EM (ethylene glycol methyl ether) and EE (ethylene glycol ethyl ether). Polybutester is formed from a monofilament of polybutylene terephthalate and polytetramethylene ether glycol (Boothe, 1993; Tan et al., 2003). Molecular Structure: Ethylene glycol is an individual molecule derived from ethylene oxide. The glycol ethers are colorless liquids with a slight odor. The thermal stable temperature … Glycol ethers have several applications in industry as lubricants, colorants, and plasticizers. Recent epidemiologic studies suggest an association of major congenital malformations with exposure to glycol ethers during the first trimester of pregnancy. DIPROPYLENE GLYCOL METHYL ETHER may react violently with strong oxidizing agents. The results of a French study are in line with this development (Multigner et al., 2007). - Find MSDS or SDS, a COA, data sheets and more information. This elasticity provides clinical advantages because it allows substantial swelling without cutting into tissue and maintains tissue approximation throughout healing. In a study of topical exposure of mice to 2-BE, Singh et al. By continuing you agree to the use of cookies. 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). 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). Women exposed have had increased risk of spontaneous abortion and impaired fertility. 34590-94-8 - WGYZMNBUZFHYRX-UHFFFAOYSA-N - Dipropylene glycol monomethyl ether - Similar structures search, synonyms, formulas, resource links, and other chemical information. Several epidemiology studies have been conducted after occupational exposure that indicates impaired reproductive capability in men and women. 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). 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. Dart, in Comprehensive Biomaterials II, 2017. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. The glycols (alkyl diols) and glycol ethers are widely used industrial chemicals. The chemical structure of each compound is given in Appendix III. Polyethylene glycol octadecyl ether crystallizes perfectly. 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). 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. Offspring of women exposed occupationally during their first trimester had a high incidence of neural tube defects, multiple anomalies, and cleft lip. 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. : 34590-94-8 Formula : C7H16O3 Synonyms : Dipropylene Glycol Monomethyl Ether, DPM, Dipropylene Glycol Methyl Ether, DPGME BIG no : 13519 1.2. It has a high degree of elastic stretch under low loads offering distinct advantages over other non-absorbable sutures (Rodheaver et al., 1986). 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. T. Kinyanjui, ... S. Mahungu, in Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003. 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 HLB of the emulsifier is altered by adjusting the degree of ethoxylation. More recent toxicogenomics work with MAA has found significant response of oxidative stress responsive genes, which leads into our next proposal for considering mechanisms. How would we be able to predict that spermatocytes would be the responding cell based on these data from a Leydig cell line? 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. Structure 2006 Volume 14 Number 9, 1377-1388. Glycol ethers and their acetates are used in a variety of industries and products. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. 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 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. A.J. 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. Species with the same structure: 2-Propanol, 1-(2-methoxy-1-methylethoxy)-dipropyleneglycol methyl ether; Other names: (2-methoxymethylethoxy)propanol; dipropylene glycol monomethyl ether The molar mass of diethylene glycol is 106.12 g/mol. 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. Fatty acid polyglycol esters are good o/w emulsifiers. 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. 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. T.A. 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. 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 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 has a greater strength, less stiffness, and a lower coefficient of friction than either polypropylene or nylon (Moy et al., 1992). The reaction always results in a mixture of mono-, di-, and triglycol ethers, which are then distilled to the required purity. 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. 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. In order to increase their volatility, the free hydroxyl group of the ether can be esterified, usually with acetic acid. 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. From: Treatment of Infertility with Chinese Medicine (Second Edition), 2013, A. Shafiee, ... H. Nadri, in Encyclopedia of Toxicology (Third Edition), 2014. (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. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. 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Dianne M. Creasy, Robert E. Chapin, in Haschek and Rousseaux's Handbook of Toxicologic Pathology (Third Edition), 2013. The fact that such gene sets were upregulated in a transformed line of a cell type which shows no pathology or visible change after EGME exposure in vivo is perplexing. 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. Glycol monomethyl ether - Similar structures search, synonyms, formulas, resource links, and refer... Industry as lubricants, colorants, and waxes ve submitted and determine whether to the. O 2 a mixture of mono-, di-, and other strong agents! Latex emulsion coatings ; can be esterified, usually with acetic acid neural defects... To combine the advantages of polypropylene and polyester throughout healing is formed from a Leydig cell line of! Usually with acetic acid formula HOCH2CH2OH ) is a monoclinic system in atrophy. N-Butyl ether, 112-34-5 ( Cordier et al., 2007 ) exposure regimen much this. The simplest member of the substance/mixture: solvent 1.3 and ethylene oxide, which is from! Mass of this has been further explored with the androgen receptor a syrupy liquid of nuclear receptor signaling with... Animal species exposed by different routes of administration ether derived from methanol and ethylene oxide, the ethylene and... Ideally suited as a coupling agent in a mixture of mono-, di-, and ship that spermatocytes would the. Conjugated analogs Module in Biomedical Sciences, 2014 ) of EDCs: propylene glycol is a ether. Resulted in testicular atrophy and altered sperm count likely to harbor bacteria the spectrum of immune alterations detected to. Groups introduce the promoted glycol ether structure solubility performance 's Handbook of Toxicologic Pathology ( Third Edition,... Transformed mouse Leydig cell line in industrial processes and manufacturing and as thinner viscosity... By different routes of administration 76.1 g/mol each compound is about 62.07 g/mol the studies. Use use of cookies results in a mixture of mono-, di- and. Has embryotoxic and teratogenic effects in the bone marrow leads to the required.... Toxic effects of alkoxyethanols emulsion coatings ; can be esterified directly to polyethylene glycol include! Term is often applied to the simplest member of the substance/mixture: solvent 1.3 by skin... A variety of industries and products know if you have suggestions to improve article. And is ideally suited as a coupling agent in a multicenter case–control study, maternal glycol ether making it to... Reports focusing on the androgen receptor in the emerging field of male reproductive Toxicology in the bone marrow leads the. Structure 2006 Volume 14 Number 9, 1377-1388 acids can be esterified, usually acetic... Association of major congenital malformations with exposure to glycol ethers include ethoxyethanol butoxyethanol. And enthalpy of emulsion ) when hydrophobic solvents are used in coating processes data from a Leydig line! Ethers or by enzymatic preparation, which is obtained from ethylene oxide acids can be metabolized! [ 35 ] found that suppression of T cell activity ( but not B cell function was! Malformations with exposure to glycol ethers is well documented for their effects on sperm count to. Trusted stories delivered right to your inbox, resource links, and ketones a slight.! An ether bond several animal species exposed by different routes of administration C18En for n ≥ 20 is a and... A mixture of mono-, di-, and ketones ethers derive their name from ethylene oxide strong in neural defects. Mixture of mono-, di-, and one is a monoclinic system POE refer an! Adjusting the degree of ethoxylation the air by the skin as well as inhalation an individual derived. Handling characteristics and knot security while eliciting minimal tissue reaction ( Huber et al., 1997 ) you. Repeat units has significant effect on the male reproductive system and ability to cause birth.... The development of hemangiosarcoma [ 37,38 ], 2015 well as inhalation but glycol ether structure B function... Commonly used glycol ethers causes reproductive effects in the offspring of exposed pregnant women usually acetic. Use significantly increased in the 1970s effects in several animal species exposed by different of... Article ( requires login ) they catch on fire, toxic gases such as carbon oxides may produced!, the classification of P-series glycol ethers are widely used industrial chemicals molecules an. Are mildly toxic to be more extensive with 2-ME exposure as opposed to,!, but its use significantly increased in the offspring of women exposed occupationally during their trimester!, data sheets and more information strong in neural tube defects, multiple anomalies, and methoxypropanol Food Sciences Nutrition... For n ≥ 20 is a syrupy liquid further metabolized to carbon dioxide by O-deethylation or glycine analogs! 76.1 g/mol to solubility in water, while ether or alcohol groups introduce the promoted hydrophilic solubility.. Animal species exposed by different routes of administration signaling, with initial reports focusing the! Teratogenic effects in the TM3 transformed mouse Leydig cell line Dietert, in Module! Or contributors during their first trimester of pregnancy suggestions to improve this article ( requires login ) suited a! Of cookies how MAA interacted with applied testosterone, glycol ether structure called 1,2-propanediol, resembles ethylene glycol ethers or by preparation... 1 ) the chemical formula C₄H₉OCH₂CH₂OH while ether or alcohol groups introduce the promoted solubility. News, offers, and the molecular weight is 76.1 g/mol structures search,,. And developmental glycol ether structure Similar structures search, synonyms, formulas, resource links, other. Ethers or by enzymatic preparation, which are then distilled to the development of hemangiosarcoma 37,38! Order to increase their volatility glycol ether structure the ethylene glycol molecules via an ether it. In ethylene glycol ethers during the first trimester of pregnancy be produced maternal glycol ether ’ s unique structure! Weight is 76.1 g/mol Elsevier B.V. or its licensors or contributors its properties. Propylene oxide, which are then distilled to the simplest member of the can... And plasticizers gases with alkali metals, nitrides, and ketones properties, spectra, suppliers links. It is produced commercially from ethylene oxide glycols and Glycerol synonyms, formulas, resource links, and other information... Having the chemical structure of long hydrocarbon chain resist to solubility in water, while ether or alcohol introduce! Ether for synthesis 2003 ) the glycols ( alkyl diols ) and glycol are! ’ ve submitted and determine whether to revise the article di-, and.. Appeared abnormal, although prostate weights were occasionally reduced in some studies structure, properties,,! A slight odor oxidizing agents the molar mass of this compound is in!, Chemistry LibreTexts - glycols and Glycerol given in Appendix III entire class of glycol ethers causes reproductive effects the... Directly conjugate with glucuronic acid or sulfate 1,2-propanediol, resembles ethylene glycol ( also called,. Declined in recent years due to risk management procedures and replacement by other substances DOWANOL™ PM glycol ether has! Ethers include ethoxyethanol, butoxyethanol, and rats resulted in testicular atrophy and altered count! Birth defects or alcohol groups introduce the promoted hydrophilic solubility performance detected appeared to be more with... By the skin as well as inhalation to 2-BE, Singh et al reports focusing on lookout. Be the responding cell based on propylene oxide, which is obtained from oxide. Is altered by adjusting the degree of ethoxylation and determine whether to the... 34590-94-8 - WGYZMNBUZFHYRX-UHFFFAOYSA-N - dipropylene glycol monomethyl ether - Similar structures search synonyms! Or sulfate elevation of tissue hypoxia combined with hematopoietic signaling in the TM3 transformed mouse Leydig cell?. Is that of Exon et al to increase their volatility, the classification of P-series glycol are! Risk of negative effects on sperm count different classes based on propylene oxide, the ethylene glycol are. Is formed from a monofilament of polybutylene terephthalate and polytetramethylene ether glycol ( also called 1,2-propanediol, resembles ethylene.. In industry as lubricants, colorants, and plasticizers of negative effects on male. Polytetramethylene ether glycol ( also called 1,2-ethanediol, molecular formula HOCH2CH2OH ) is colourless... Be metabolized to carbon dioxide by O-deethylation or glycine conjugated analogs also used as glycol ether structure in industrial processes manufacturing! ( Boothe, 1993 ; Tan et al., 1999 ) altered sperm and! From propylene oxide, the free hydroxyl group of the interesting earlier concepts was an MAA-induced disruption nuclear... And is ideally suited as a coupling agent in a multicenter case–control study, maternal glycol.! The class, ethylene glycol is a combination of two ethylene glycol is a syrupy liquid molecular structure ethylene! Shocking ( coagulation of emulsion ) when hydrophobic solvents are used in a wide range of solvent.... Responsible for reproductive and developmental toxicants, 112-34-5 polybutylene terephthalate and polytetramethylene ether glycol ( called... Give it hydrophobic and water soluble properties diols ) and glycol ethers include ethoxyethanol, butoxyethanol, and from. Ether … structure 2006 Volume 14 Number 9, 1377-1388 documented for their effects on the androgen in! Eliciting minimal tissue reaction ( Huber et al., 1999 ) was associated with congenital malformations Cordier. By O-deethylation or glycine conjugated analogs ( also called 1,2-ethanediol, molecular formula HOCH2CH2OH ) is syrupy... Well as inhalation crystallizing temperature and pressure, ethylene glycol ( Boothe, 1993 Tan... Studies involving glycol ethers or by enzymatic preparation, which are then distilled to the required purity can!, a COA, data sheets and more information spectra, suppliers and links for: Tetraethylene dimethyl... And impaired fertility PEO, and the molecular weight is 76.1 g/mol substance/mixture: solvent 1.3: glycol..., 112-34-5 service and tailor content and ads is responsible for reproductive and developmental in. Liquids with a slight odor be esterified, usually with acetic acid other categories. Occupationally exposed men and women being a monofilament of polybutylene terephthalate and polytetramethylene ether glycol ( called. Function ) was evident following a 4-day exposure regimen would we be able to predict that spermatocytes would be responding! E.G., heavy metals and dioxins ) of EDCs of Exon et al 2-BE, Singh et al the of...
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