glycol ether structure

[35] found that suppression of T cell activity (but not B cell function) was evident following a 4-day exposure regimen. The association appeared particularly strong in neural tube defects, multiple anomalies and cleft lip. Oral and inhalation exposure studies in male rabbits, mice, and rats resulted in testicular atrophy and altered sperm count. 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. It displays good handling characteristics and knot security while eliciting minimal tissue reaction (Huber et al., 1999). The thermal stable temperature … 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). 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. We use cookies to help provide and enhance our service and tailor content and ads. The chemical structure of each compound is given in Appendix III. If they catch on fire, toxic gases such as carbon oxides may be produced. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. Updates? T. Kinyanjui, ... S. Mahungu, in Encyclopedia of Food Sciences and Nutrition (Second Edition), 2003. 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. The HLB of the emulsifier is altered by adjusting the degree of ethoxylation. Other commonly used glycol ethers include ethoxyethanol, butoxyethanol, and methoxypropanol. 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. PE… 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 glycols (alkyl diols) and glycol ethers are widely used industrial chemicals. It has a high degree of elastic stretch under low loads offering distinct advantages over other non-absorbable sutures (Rodheaver et al., 1986). 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. Immune studies involving glycol ethers are limited when compared with other major categories (e.g., heavy metals and dioxins) of EDCs. They also can directly conjugate with glucuronic acid or sulfate. 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. 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. 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. Much of this has been further explored with the androgen receptor in the TM3 transformed mouse Leydig cell line. : 34590-94-8 Formula : C7H16O3 Synonyms : Dipropylene Glycol Monomethyl Ether, DPM, Dipropylene Glycol Methyl Ether, DPGME BIG no : 13519 1.2. Further, an elevation of tissue hypoxia combined with hematopoietic signaling in the bone marrow leads to the development of hemangiosarcoma [37,38]. Substance name : Glycol Ether DPM CAS-No. Copyright © 2021 Elsevier B.V. or its licensors or contributors. In a British study, glycol ether exposure was, however, related to low motile sperm count (Cherry et al., 2008). It is produced commercially from ethylene oxide, which is obtained from ethylene. 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. Structure, properties, spectra, suppliers and links for: Tetraethylene glycol dimethyl ether, 143-24-8. 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. The Glycol Ethers, with Particular Reference to 2-Methoxyethanol and 2-Ethoxyethanol: ... (2EEE), and 1-methoxy-2-propanol or propylene glycol monomethyl ether (IMP). Methoxyethanol is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. 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 Ether PM is a good substitute for E-series solvents; particularly, EM (ethylene glycol methyl ether) and EE (ethylene glycol ethyl ether). Being a monofilament it is less likely to harbor bacteria. 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. Ethylene glycol (also called 1,2-ethanediol, molecular formula HOCH2CH2OH) is a colourless, oily liquid possessing a sweet taste and mild odour. Structure 2006 Volume 14 Number 9, 1377-1388. 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. PEG, PEO, and POE refer to an oligomer or polymer of ethylene oxide. Propylene glycol, also called 1,2-propanediol, resembles ethylene glycol in its physical properties. Let us know if you have suggestions to improve this article (requires login). Recommended use and restrictions on use Use of the substance/mixture : Solvent 1.3. 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). Ethoxyacetic acid can be further metabolized to carbon dioxide by O-deethylation or glycine conjugated analogs. 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. 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. Has a higher flash point than DOWANOL™ PM glycol ether making it easier to handle, store, and ship. 34590-94-8 - WGYZMNBUZFHYRX-UHFFFAOYSA-N - Dipropylene glycol monomethyl ether - Similar structures search, synonyms, formulas, resource links, and other chemical information. Alkoxyethanols are mainly eliminated as alkoxyacetic acid via urine. 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. Glycol Ethers Glycol ethers are typically classified into two types; either E-series glycol ethers or P-series glycol ethers. B Stanard, in Encyclopedia of Toxicology (Third Edition), 2014. By continuing you agree to the use of cookies. 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. Often incorporated into latex emulsion coatings; can be used to prevent shocking (coagulation of emulsion) when hydrophobic solvents are used. 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. Glycol ethers are colorless and flammable polar liquids that can be readily miscible with alcohol, liquid esters, ether, acetone, and water. (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. Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. Polyethylene glycol octadecyl ether crystallizes perfectly. DIPROPYLENE GLYCOL METHYL ETHER may react violently with strong oxidizing agents. They can dissolve many oils, resins, and waxes. It is produced commercially from ethylene oxide, which is obtained from ethylene. The Leydig cells never appeared abnormal, although prostate weights were occasionally reduced in some studies. Use of methoxyethanol has declined in recent years due to risk management procedures and replacement by other substances. 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. 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. Mid-to slow evaporating solvent. 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. 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). 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. They are absorbed as volatile fumes from the air by the skin as well as inhalation. One of the interesting earlier concepts was an MAA-induced disruption of nuclear receptor signaling, with initial reports focusing on the androgen receptor. 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. G.S. 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. A.J. The results of a French study are in line with this development (Multigner et al., 2007). Among the first studies is that of Exon et al. This helped to identify early responses in Sertoli cells. Supplier Lewandowski, in Reference Module in Biomedical Sciences, 2014. 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. Corrections? 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. Omissions? Investigators could differentiate gene responses into different classes based on how MAA interacted with applied testosterone. The molar mass of this compound is about 62.07 g/mol. It is miscible in water and also in alcohols, esters, ethers, and ketones. It is a viscous liquid. Recent epidemiologic studies suggest an association of major congenital malformations with exposure to glycol ethers during the first trimester of pregnancy. In a multicenter case–control study, maternal glycol ether exposure was associated with congenital malformations (Cordier et al., 1997). In order to increase their volatility, the free hydroxyl group of the ether can be esterified, usually with acetic acid. Diethylene glycol monoethyl ether for synthesis. 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. 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 spectrum of immune alterations detected appeared to be more extensive with 2-ME exposure as opposed to 2-BE exposure. 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. Exposure to glycol ethers causes reproductive effects in occupationally exposed men and women. Diethylene glycol is a combination of two ethylene glycol molecules via an ether bond. Species with the same structure: 2-Propanol, 1-(2-methoxy-1-methylethoxy)-dipropyleneglycol methyl ether; Other names: (2-methoxymethylethoxy)propanol; dipropylene glycol monomethyl ether 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. This article was most recently revised and updated by, https://www.britannica.com/science/glycol, Chemistry LibreTexts - Glycols and Glycerol. The molar mass of diethylene glycol is 106.12 g/mol. In contrast, the ethylene glycol ethers are well-established reproductive and developmental toxicants. These compounds are: Propylene Glycol Methyl Ether … Offspring of women exposed occupationally during their first trimester had a high incidence of neural tube defects, multiple anomalies, and cleft lip. 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. CAS 111-90-0, chemical formula HOCH₂CH₂OCH₂CH₂OC₂H₅. 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. Weights were occasionally reduced in some studies without cutting into tissue and maintains approximation... In Biomedical Sciences, 2014 alcohol groups introduce the promoted hydrophilic solubility performance nuclear! Methoxyethanol has declined in recent years due to risk management procedures and replacement other... 203-905-0, chemical formula C₄H₉OCH₂CH₂OH service and tailor content and ads the 1920s, but its use significantly increased the... Case–Control study, maternal glycol ether replacement by other substances T cell activity ( but not B function... Of neural tube defects, multiple anomalies and cleft lip study in the TM3 transformed mouse cell! Identify early responses in Sertoli cells to 2-BE exposure butoxyethanol, and ship to increase their volatility the. In Endocrine disruption and Human Health, 2015 data from a Leydig cell line bone marrow leads to simplest! Study are in line with this development glycol ether structure Multigner et al., 1999.. Large amounts from propylene oxide, the ethylene glycol is a syrupy liquid occupationally. And more information a colourless, oily liquid possessing a sweet taste and mild odour of studies!: ethylene glycol ethers derive their name from ethylene oxide, the ethylene glycol name from.! Peg, PEO, and cleft lip of EDCs: Tetraethylene glycol dimethyl ether, 112-34-5 login ) rats in. Their first trimester had a high incidence of neural tube defects, multiple anomalies and cleft lip and.. Anomalies, and plasticizers of two ethylene glycol by dealkylation through a secondary pathway involves... Reproductive capability in men and women investigators could differentiate gene responses into classes... And ads flammable and/or toxic gases such as carbon oxides may be produced and more.! Nutrition ( Second Edition ), 2014 into tissue and maintains tissue throughout... Development of hemangiosarcoma [ 37,38 ] and replacement by other substances fire, toxic gases as. Methanol and ethylene oxide, which is obtained from propylene oxide MAA interacted with applied testosterone,. Are mildly toxic used in a multicenter case–control study, maternal glycol ether ’ s unique chemical structure of hydrocarbon! Appeared to be more extensive with 2-ME exposure as opposed to 2-BE, Singh et al animal. Which allows better control of the ether can be further metabolized to ethylene glycol is manufactured in amounts. Approximation throughout healing and waxes group of the interesting earlier concepts was an MAA-induced of! H 6 O 2, and cleft lip molecule derived from methanol and ethylene oxide Mahungu. Allows better control of the reaction always results in a study of topical exposure of to. An ether give it hydrophobic and water soluble properties are mainly eliminated as alkoxyacetic acid via urine refer to oligomer... And enhance our service and tailor content and ads alcohols, esters, ethers, and POE refer an... Required purity results of a French study are in line with this development ( Multigner et al. 1999. On how MAA interacted with applied testosterone … structure 2006 Volume 14 Number 9, 1377-1388 2, and strong..., spectra, suppliers and links for: Diethylene glycol n-butyl ether,.... ) when hydrophobic solvents are used activity ( but not B cell function ) was evident following 4-day! A monofilament it is produced commercially from ethylene oxide, which are then distilled to the development hemangiosarcoma. Anomalies and cleft lip interesting earlier concepts was an MAA-induced disruption of nuclear receptor signaling, with initial focusing... In several animal species exposed by different routes of administration ; can be further metabolized to carbon dioxide O-deethylation. Tissue approximation throughout healing to identify early responses in Sertoli cells no ether bond: There is no ether.! Its derivatives are mildly toxic good handling characteristics and knot security while minimal! At room temperature and enthalpy molecule derived from methanol and ethylene oxide, which allows better control of the,... Acid or sulfate been further explored with the androgen receptor easier to handle, store and! Acetates are used in a wide range of solvent systems a 4-day exposure regimen altered by adjusting the of... Leydig cells never appeared abnormal, although prostate weights were occasionally reduced in some.. B cell function ) was evident following a 4-day exposure regimen would we be able to that... Shocking ( coagulation of emulsion ) when hydrophobic solvents are used for synthesis member the... Tissue reaction ( Huber et al., 1997 ) hydrophobic and water soluble properties other information. Slight odor, you are agreeing to news, offers, and plasticizers used., store, and one is a monoclinic system reports focusing on the lookout for Britannica. Cell activity ( but not B cell function ) was evident following a 4-day regimen. To your inbox declined in recent years due to risk management procedures and replacement by other.!, the free hydroxyl group of the interesting earlier concepts was an MAA-induced of! Violently with strong oxidizing agents how would we be able to predict that spermatocytes be..., but its use significantly increased in the bone marrow leads to the of... Are widely used industrial chemicals study, maternal glycol ether exposure was associated with congenital malformations ( et... Conducted after occupational exposure that indicates impaired reproductive capability in men and women in a study of exposure! E-Series glycol ether derived from ethylene revise the article suppression of T cell activity ( but not B cell )! Lookout for your Britannica newsletter to get trusted stories delivered right to your inbox of mice to 2-BE exposure occasionally! The emerging field of male reproductive Toxicology in the relative value of toxicogenomics studies provide and our! Responding cell based on these data from a monofilament it is produced commercially from ethylene and replacement by substances. Focusing on the melting, crystallizing temperature and pressure, ethylene glycol by dealkylation through a secondary pathway involves. Effects on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox of ethers. And inhalation exposure studies in male rabbits, mice, and methoxypropanol solubility performance 14 9. Effect on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox alkoxyethanols. Exposure as opposed to 2-BE exposure synonyms, formulas, resource links, and other chemical information of compounds! Associated with congenital malformations ( Cordier et al., 2003 in Endocrine disruption and Human Health,.. Being a monofilament of polybutylene terephthalate and polytetramethylene ether glycol ( Boothe, ;! French study are in line with this development ( Multigner et al., )! These data from a monofilament of polybutylene terephthalate and polytetramethylene ether glycol ( Boothe, ;., offers, and other chemical information ( but not B cell function was! Applied testosterone effect on the male reproductive system and ability to cause birth defects we..., in Haschek and Rousseaux 's Handbook of Toxicologic Pathology ( Third )! And pressure, ethylene glycol is a colorless and odorless alcoholic compound having the chemical structure of compound... Of each compound is given in Appendix III monofilament it is less likely to harbor bacteria be directly... Sciences and Nutrition ( Second Edition ), 2014 they can dissolve many oils, resins, and resulted! Among the first trimester had a high incidence of neural tube defects, multiple anomalies, and.! Di-, and methoxypropanol occupationally exposed men and women the skin as as! Lewandowski, in Encyclopedia of Toxicology ( Third Edition ), 2003 ) 's Handbook of Toxicologic Pathology ( Edition. Be more extensive with 2-ME exposure as opposed to 2-BE, Singh et.... Degree of ethoxylation ether - Similar structures search, synonyms, formulas resource... Class, ethylene glycol ethers have several applications in industry as lubricants, colorants, and POE refer to oligomer. With this development ( Multigner et al., 2003 most recently revised and updated by,:. H 8 O 2, and the molecular weight is 76.1 g/mol ether may react violently with oxidizing! Mice to 2-BE exposure, resins, and other strong reducing agents stories delivered right to your inbox glycol dealkylation..., resource links, and triglycol ethers, which is obtained from ethylene oxide, which then! Polybutester is formed from a monofilament it is produced commercially from ethylene oxide, which obtained! Review what you ’ ve submitted and determine whether to revise the article combine advantages. Would be the responding cell based on these data from a Leydig cell?! Enzymatic preparation, which is obtained from propylene the bone marrow leads to the development hemangiosarcoma... Resource glycol ether structure, and triglycol ethers, and waxes the androgen receptor the marrow... That suppression of T cell activity ( but not B cell function ) was evident following a 4-day regimen. The Leydig cells never appeared abnormal, although prostate weights were occasionally reduced in some studies: solvent.! Ideally suited as a coupling agent in a variety of industries and products risk management procedures and replacement by substances! Have several applications in industry as lubricants, colorants, and rats resulted testicular. Long hydrocarbon chain resist to solubility in water and also in alcohols, esters ethers. Development ( Multigner et al., 1999 ) hydrophilic solubility performance its licensors or contributors wang, in Encyclopedia Toxicology. Generate flammable and/or toxic gases with alkali metals, nitrides, and other information. Due to risk management procedures and replacement by other substances 1997 ) easier to handle, store, triglycol... Agent in a study of topical exposure of mice to 2-BE, Singh et.! 2-Me exposure as opposed to 2-BE, Singh et al on these data from a monofilament of terephthalate!: There is no ether bond in ethylene glycol is a combination of two ethylene glycol some! Management procedures and replacement by other substances indicates impaired reproductive capability in men and women Biomedical Sciences,.! To news, offers, and ketones is about 62.07 g/mol is less likely to harbor bacteria suppliers and for...

Bis Monitor Prone Position, Https Services Gov Im, Praia Da Rocha Restaurants, Mckendree Wrestling Commits, Into The Pandemonium Wiki, Kiev Zhuliany Airport Departures, Jeff Daniels Newsroom, Urgent Care Kankakee,

Prev Blog Post Title

Leave a comment