2-Methoxy-ethanol

2-Methoxyethanol

HCID 8019CAS 109-86-4

Grundinformationen

Standard-SMILES
COCCO
InChIKey
XNWFRZJHXBZDAG-UHFFFAOYSA-N
Summenformel
C3H8O2
Durchschnittliche Molmasse
76,09 g/mol
Monoisotopische Masse
76,05242949

Namen und Bezeichner

Bevorzugter Name
2-Methoxyethanol
IUPAC
2-methoxyethanol
Lokaler Name
2-Methoxy-ethanol
Englischer Name
2-Methoxyethanol
Summenformel
C3H8O2
Molmasse
76.09

Namen und Synonyme

2-METHOXYETHANOL109-86-4Methyl cellosolveEthylene glycol monomethyl etherEthanol, 2-methoxy-Methyl oxitol2-Methoxy-1-ethanolDowanol EMMethylglykolEGMEMethoxyhydroxyethane3-Oxa-1-butanol
Weitere Namen anzeigen
H2OAMYL ALCOHOLMETHOXYETHANOLDISTILLED WATEREthylene glycol methyl etherEGM
Monomethyl glycolGlycol ether EMPristGlycol monomethyl ether1-Hydroxy-2-methoxyethaneJeffersol EMMECSMetil cellosolve

Datenbank-Bezeichner

CAS
109-86-4、32718-54-0
PubChem CID
8019
DTXSID
DTXSID5024182
ChEMBL
CHEMBL444144
ChEBI
CHEBI:46790
UNII
EK1L6XWI56
EC Number
203-713-7、251-174-1
Nikkaji
J2.442B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,8
Polarare Oberfläche (TPSA)
29,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
5

Experimentelle und physikochemische Eigenschaften

LogP · 3 Einträge

-0.77

log Kow = -0.77

-0.503

Odor · 2 Einträge

Mild agreeable odor

Ether-like odor

TasteBitter
Density · 6 Einträge

0.966 at 68 °F (USCG, 1999) - Less dense than water; will float

0.9647 g/cu cm at 20 °C

Bulk density: 8.0 lb/gal

Relative density (water = 1): 0.96

0.96

1.4 @ 20°C

Color/FormColorless liquid
Solubility · 6 Einträge

greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)

1000000

Miscible with water

Miscible with alcohol, ether, acetone, dimethylformamide

Miscible with hydrocarbons, alcohols, ketones, glycols

Solubility in water: miscible

Physikochemische Eigenschaften

Schmelzpunkt
-85 °C · -85 °C
Siedepunkt
124 · 124-125 °C(lit.)
Dichte
0.965 g/mL · 0.965 g/mL at 25 °C(lit.)
Dampfdichte
2.62 · 2.62 (vs air)
Dampfdruck
6.17 mm · 6.17 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.402(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids];H302: Harmful if swallowed [Warning Acute toxicity, oral];H312: Harmful in contact with skin [Warning Acute toxicity, dermal];H332: Harmful if inhaled [Warning Acute toxicity, inhalation];H360FD: May damage fertility; May damage the unborn child [Danger Reproductive toxicity]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P318, P321, P330, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Ethanol, 2-methoxy-

Hazard Traits - Developmental Toxicity; Reproductive Toxicity;Authoritative List - CA TACs; EC Annex VI CMRs - Cat. 1B; OEHHA RELs; Prop 65;Report - regardless of intended function of ingredient in the product

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanol, 2-methoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-methoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

S - indicates a substance that is identified in a final Significant New Use Rule.

Status: Active Update: 02-09-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/14919

Other Safety InformationIMAP assessments - Alkoxyethanols (C1-C2) and their acetates: Human health tier II assessment;IMAP assessments - Ethanol, 2-methoxy-: Environment tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:;HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. CAUTION: Ethanol (UN1170) can burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.) Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. (ERG, 2024)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;CAUTION: Ethanol (UN1170) can burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.);· Vapors may form explosive mixtures with air.;· Vapors may travel to source of ignition and flash back.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapor explosion hazard indoors, outdoors or in sewers.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Runoff to sewer may create fire or explosion hazard.;· Containers may explode when heated.;· Many liquids will float on water.

Flammable. Above 39 °C explosive vapour/air mixtures may be formed.

Fire PotentialFlammable
Health Hazards · 2 Einträge

Irritation of skin and eyes. Chronic exposure may also cause weakness, sleepiness, headache, gastrointestinal upset, weight loss, change of personality. (USCG, 1999)

· Inhalation or contact with material may irritate or burn skin and eyes.;· Fire may produce irritating, corrosive and/or toxic gases.;· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.;· Runoff from fire control or dilution water may cause environmental contamination.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: For fire involving UN1170, UN1987 or UN3475, alcohol-resistant foam should be used. CAUTION: Ethanol (UN1170) can burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.).;SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam.;LARGE FIRE: Water spray, fog or alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· All equipment used when handling the product must be grounded.;· Do not touch or walk through spilled material.;· Stop leak if you can do it without risk.;· Prevent entry into waterways, sewers, basements or confined areas.;· A vapor-suppressing foam may be used to reduce vapors.;· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.;· Use clean, non-sparking tools to collect absorbed material.;Large Spill;· Dike far ahead of liquid spill for later disposal.;· Water spray may reduce vapor, but may not prevent ignition in closed spaces.

First Aid · 3 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· Wash skin with soap and water.

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Water flush promptly - If this chemical contacts the skin, flush the contaminated skin with water promptly. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water promptly. If irritation persists after washing, get medical attention.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageFireproof. Separated from strong oxidants and food and feedstuffs. Keep in the dark. Cool.
Exposure Control and Personal Protection · 3 Einträge

· Wear positive pressure self-contained breathing apparatus (SCBA).;· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

Biological Exposure Indices (BEI) [ACGIH] - 2-Methoxyacetic acid in urine = 1 mg/g creatinine; end of shift at end of workweek; [ACGIH]

1.0 [ppm], sum of concentrations of CAS 109-86-4 and its acetate in air[German Research Foundation (DFG)]

Toxikologische Informationen

Interactions · 5 Einträge

... A single exposure of mice to 125 ppm /2-methoxyethanol/ for 4 hr potentiated the hypnotic effects of barbiturates; at 500 ppm for 4 hr, spontaneous motor activity decreased.

The iv LD50 of serratia marcescens endotoxin in mice was 17 mg/kg. However, when the endotoxin was followed immediately by 950 mg iv methyl cellosolve, the LD50 dropped to 0.25 mg/kg. Ip methyl cellosolve also caused potentiation as did the pre-incubation of methyl cellosolve and endotoxin prior to injection.

In adult female SPF Sprague-Dawley rats exposed for 2 hr to 1600 ppm 2-methoxyethanol (ME) the blood level of ME was considerably increased after pretreatment with ethanol (20 mmol/kg, ip). The blood level of ME remained nearly constant after the co-administration of ME (10 mm/kg, ip) with ethanol (20 mmol/kg), as long as ethanol levels in the blood remained above 3 mmol/l. Repeated ip dosing (five times one injection per hour) with ME (5mmol/kg) plus ethanol (8 or 10 mmol/kg) each resulted in an almost complete accumulation of ME. The prolonged retention of ME is due to an inhibition of its degradation via competition with ethanol for alcohol dehydrogenase.

Ethylene glycol monomethyl ether (EGME) was administered to young male rats at doses varying from 50 to 500 mg/kg/day for 11 days. At sequential times animals were killed and testicular histology examined. The initial and major site of damage was restricted to the primary spermatocytes undergoing post zygotene meiotic maturation and division. When animals were treated with inhibitors of alcohol metabolism followed by a testicular toxic dose of EGME (500 mg/kg) an inhibitor of alcohol dehydrogenase (pyrazole) offered complete protection. However pretreatment with aldehyde dehydrogenase inhibitors disulfiram or pargyline did not ameliorate the testicular toxicity of EGME.

For more Interactions (Complete) data for 2-METHOXYETHANOL (14 total), please visit the HSDB record page.

Target Organs · 2 Einträge

Reproductive

Eyes, respiratory system, central nervous system, blood, kidneys, reproductive system, hematopoietic system

Ecotoxicity Values · 5 Einträge

LC50; Species: Lepomis macrochirus (bluegill); Conditions: /Static bioassay in fresh water at 23 °C, mild aeration applied after 24 hr/; Concentration: >10,000 ppm for 96 hr

LC50; Species: Menidia beryllina (inland silverside); Conditions: Static bioassay in synthetic seawater at 23 °C, mild aeration applied after 24 hr; Concentration: >10,000 mg/L for 96 hr

LC50; Species: Guppy (Poecilia reticulata); Concentration: 17,400 mg/L for 7 days /Conditions of bioassay not specified in source examined/

LC50; Species: Leuciscus idus (ide); Conditions: static; Concentration: >10000 mg/L for 48 hr

For more Ecotoxicity Values (Complete) data for 2-METHOXYETHANOL (12 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a log Kow of -0.77(2) and a regression-derived equation(3), indicates that 2-methoxyethanol is expected to have very high mobility in soil(SRC). Volatilization of 2-methoxyethanol from moist soil surfaces is expected to be an environmental fate process(SRC) given a Henry's Law constant of 3.3X10-7 atm-cu m/mole(4). The potential for volatilization of 2-methoxyethanol from dry soil surfaces may exist(SRC) based upon a vapor pressure of 9.5 mm Hg(5). Utilizing the Japanese MITI test, 83% of the Theoretical BOD was reached in 2 weeks(6) indicating that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a log Kow of -0.77(2) and a regression-derived equation(3), indicates that 2-methoxyethanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may occur(4) based upon a Henry's Law constant of 3.3X10-7 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 97 days and 700 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 83% of the Theoretical BOD was reached in 2 weeks(7) indicating that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methoxyethanol, which has a vapor pressure of 9.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methoxyethanol 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 31 hours(SRC), calculated from its rate constant of 1.25X10-11 cu cm/molecule-sec at 25 °C(3). 2-Methoxyethanol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse Effects · 2 Einträge

Neurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.;Aplastic anemia - The presence of increased methemoglobin in the blood; the compound is classified as primary toxic effect.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Neurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.;Aplastic anemia - The presence of increased methemoglobin in the blood; the compound is classified as primary toxic effect.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Exposure Routes · 2 Einträge

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Regulatorische Informationen

Regulatory Information · 6 Einträge

Chemical: Ethanol, 2-methoxy-

Hazard Traits - Developmental Toxicity; Reproductive Toxicity;Authoritative List - CA TACs; EC Annex VI CMRs - Cat. 1B; OEHHA RELs; Prop 65;Report - regardless of intended function of ingredient in the product

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanol, 2-methoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-methoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

S - indicates a substance that is identified in a final Significant New Use Rule.

Status: Active Update: 02-09-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/14919

FDA RequirementsEthylene glycol monomethyl ether is an indirect food additive for use only as a component of adhesives.
FIFRA Requirements · 1 Eintrag

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Methoxyethanol is found on List C. Case No: 3036; Pesticide type: fungicide, antimicrobial; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): methoxyethanol; Data Call-in (DCI) Date(s): 09/30/1992; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Atmospheric Standards · 1 Eintrag

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Ethylene glycol monomethyl ether is produced, as an intermediate or a final product, by process units covered under this subpart.

Sicherheitsdaten

F
10
OEB
C
OEL
TWA: 0.1 ppm (0.3 mg/m3) [skin]
wgk
3
IDLA
200 ppm
tsca
TSCA listed

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 5 Einträge

Cell death was analyzed in neurulating mouse embryos after in vivo doses of 2-methoxyethanol (2-ME) that produce anterior neural tube defects. Characterization of 2-ME-induced cell death was performed by evaluating: (1) vital fluorochrome staining in whole embryos applying confocal laser scanning microscopy; (2) characteristics of cell debris in conventional histological sections revealed by light microscopy; and (3) Apoptag in situ immunohistochemical staining for apoptosis using light microscopy. ...Physiological cell death in control embryos primarily occurred in the neural crest region during neural fold elevation. Embryos exposed to 2-ME had expanded areas of cell death in the neural crest and also new areas of cell death in medial regions of the anterior neural tube. Both physiological and 2-ME-induced embryonic cell death had morphological, immunohistochemical, and fluorochrome staining characteristics of apoptosis. When fluorescence data from confocal microscopic analysis of vital fluorochrome-stained embryos were analyzed, a dose-dependent increase was found in embryos exposed to 2-ME. Similar results were obtained when cell death was analyzed in either conventional histological sections or sections prepared for immunohistochemical detection of apoptosis.

A mechanistic role for Ca2+ has been promoted. .../It was/ observed that a Ca2+ channel blocker afforded protection against 2-ME induced pachytene spermatocyte cell death. /It was/ hypothesized that 2-ME induces spermatocyte apoptosis in both the rat and guinea pig, and activates or induces an endogenous endonuclease. An increase in intracellular Ca2+ is thought by many to be the trigger for endonuclease activation/induction and subsequent apoptotic cell death.

Metabolites /of ethylene glycol monoethyl ether/ such as 2-methoxyethanol (2-ME) ...induce testicular toxicity. They may cause testicular atrophy, decreased sperm motility, and an increased incidence of abnormal sperm. Most likely, the metabolism of monoalkyl glycol ethers occurs via alcohol and aldehyde dehydrogenases, leading to the formation of methoxyacetic acid (MAA). MAA is believed to be the ultimate toxic metabolite of 2-ME. However, methoxyacetaldehyde (MALD), an intermediate metabolite of 2-ME,can also produce testicular lesions. Although the site of action was thought to be upon the late spermatocyte, it now appears that the Sertoli cells are the prime target for 2-ME. It is unclear whether the mechanism of testicular toxicity of 2-ME induces germ cell death by interfering with interregulating signal transduction pathways within either Sertoli cells or germ cells, causing a disruption of cell-to-cell communication.

Once oxidized to 2-methoxyacetic acid (2-MAA), 2-ME is teratogenic in all species tested. Upon single administration at 0800 hr, gestation day (gd) 8 (copulation plug + = gd 0) was most sensitive to induction of /exencephaly/. In this study, the effects of 2-ME/2-MAA on brain differentiation were assessed soon after gd 8 treatment. Physiological cell death (CD) in control embryos and chemically-enhanced CD were compared by Nile blue sulfate staining (4, 8, 12 hr after 2-ME; 0, 250 or 325 mg/kg). Its intensity in fore-, mid- and hindbrain was scored as scattered, moderate or intense. These CD patterns were confirmed by propidium iodide fluorescence staining. The most consistent CD staining was observed 8 hr after 325 mg 2-ME/kg. In controls, scattered CD was apparent in the pros-, mes- and rhombencephalon, while moderate to intense CD appeared uniformly in the caudal rim of the open forebrain and along its midline when closure was occurring. In 2-ME exposed embryos, CD patterns in the forebrain were comparable to those in controls. However, CD in the mid- and hindbrains was markedly increased. Moderate to intense CD in about half of the embryos was observed in the mes- and rhombencephalon. Rhombomeres 1-3 and the dorsal lateral neural tube were particularly remarkable in their staining intensity. Neural tube closure status and brain morphology (250 mg 2-ME/kg) were evaluated on gd 9.25 and gd 10.25. The mean somite number was unaffected by 2-ME treatment. However, in control embryos the neuropores were closed in all but 1 of 119 embryos, while in 23% (35 of 142; 82% of litters) of 2-ME embryos they were patent, and 8% (11 of 133; 36% of litters) still had that condition on gd 10.25. For comparison other pregnancies progressed to gd 18 when 12% of the live fetuses (in 40% of litters) had EX. There were also numerous morphological differences from developmental-age-matched controls consistent with 2-MAA-induced embryotoxicity, which caused developmental delay. Its inci

For more Mechanism of Action (Complete) data for 2-METHOXYETHANOL (16 total), please visit the HSDB record page.

Biological Half-Life · 5 Einträge

...Ethylene glycol methyl ether was found equally distributed in brain, plasma, lung, and liver 1 hr after administration and ...the half-life in the body was approx 1 to 2 hr, unless dose levels were near the lethal level. In inhalation studies the plasma levels of ethylene glycol methyl ether increased nearly linearly from exposures of 1, 2, 4, and 6 hr to 3317 ppm. When the exposure was extended to 8 hr, the concentration in the plasma was more than double that found after the 6-hr exposure, suggesting that metabolic and/or excretory mechanisms were saturated.

The human elimination half-time for the 2-methoxyacetic acid arising from the catabolism of EGME was 66 to 89 hours. /2-methoxyacetatic acid/

... . The conversion in plasma of /2-methoxyethanol/ (2-ME) to /methoxyacetic acid/ (MAA) is rapid, with a half-life of 0.6 hr in rats, ...

The role of metabolism in 2-methoxyethanol (ME)-induced testicular toxicity has been investigated with Sprague-Dawley rats. Following administration of [(14)C]ME (250 mg/kg, ip) to a group of animals, there was evidence of testicular damage, ... Radioactivity detected in urine over 48 hr after treatment accounted for 55% of the dose. ... Analysis of plasma revealed a rapid conversion of ME to MAA (t1/2 for disappearance of ME = 0.6 +/- 0.03 hr) and gradual clearance of radioactivity (t1/2 = 19.7 +/- 2.3 hr). ... Analysis of plasma revealed almost complete inhibition of the conversion of ME to MAA (t1/2 for disappearance of ME = 42.6 +/- 5.6 hr, clearance of radioactivity t1/2 = 51.0 +/- 7.8 hr). ...

For more Biological Half-Life (Complete) data for 2-METHOXYETHANOL (7 total), please visit the HSDB record page.

Metabolism/Metabolites · 5 Einträge

The metabolic transformation of /2-methoxyethanol/ (2-ME) gives two primary metabolites: /methoxyacetic acid/ (MAA) and 2-methoxyacetyl glycine. Metabolism to carbon dioxide represents a secondary, minor route. The conversion in plasma of 2-ME to MAA is rapid, with a half-life of 0.6 hr in rats, but the excretion of MAA is slow, with a half-life of about 20 hr in the rat and 77 hr in man.

The role of metabolism in 2-methoxyethanol (ME)-induced testicular toxicity has been investigated with Sprague-Dawley rats. Following administration of [(14)C]ME (250 mg/kg, ip) to a group of animals, there was evidence of testicular damage, identified as depletion of the spermatocyte population. Radioactivity detected in urine over 48 hr after treatment accounted for 55% of the dose. The major urinary metabolites were identified by HPLC and isotope dilution analysis, as methoxyacetic acid (MAA) and methoxyacetylglycine (accounting for 50 to 60% and 18 to 25%, respectively, of urinary radioactivity). Analysis of plasma revealed a rapid conversion of ME to MAA (t1/2 for disappearance of ME = 0.6 +/- 0.03 hr) and gradual clearance of radioactivity (t1/2 = 19.7 +/- 2.3 hr). Pretreatment of animals with pyrazole (400 mg/kg, ip) 1 hr prior to [(14)C]ME dosing gave complete protection against the testicular toxicity of ME. Radioactivity detected in the urine from the pyrazole-pretreated groups over 48 hr (18%) was significantly lower than in the ME-only group. The major radioactive peak co-chromatographed with ME (30 to 36% of the total urinary radioactivity). MAA and methoxyacetylglycine were not major metabolites. Analysis of plasma revealed almost complete inhibition of the conversion of ME to MAA (t1/2 for disappearance of ME = 42.6 +/- 5.6 hr, clearance of radioactivity t1/2 = 51.0 +/- 7.8 hr). The results demonstrate that metabolic activation is required for 2-methoxyethanol to exert toxicity to the male reproductive system.

The secondary metabolite of dimethoxyethyl phthalate (DMEP) methoxyacetic acid (MAA), but not the diester or its primary metabolites monomethoxyethyl phthalate and methoxyethyanol (ME) interfered with normal growth and development of organogenesis phase rat embryos in culture. These in vivo observations suggested that the teratogenicity of DMEP in vivo was due to enzymic cleavage of the diester to ME, followed by oxidation of the latter to MAA in the maternal compartment. /Metabolites of dimethoxyethyl phthalate/

When human volunteers inhaled 5 ppm EGME for 4 hours, 76% of the inspired /ethylene glycol monomethyl ether/ (EGME) was retained and 85% of the absorbed dose appeared in the urine as 2-methoxyacetic acid. The human elimination half-time for the 2-methoxyacetic acid arising from the catabolism of EGME was 66 to 89 hours.

For more Metabolism/Metabolites (Complete) data for 2-METHOXYETHANOL (20 total), please visit the HSDB record page.

MeSH Pharmacological Classification · 2 Einträge

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

An agent that causes the production of physical defects in the developing embryo.

Absorption, Distribution and Excretion · 5 Einträge

The material /2-methoxyethanol/ was detected in rat urine 30 min after an ip administration of 1.0 mg/kg and remained present for a total of 7 hr after the injection, 3 hr after it was last seen in the blood.

Male Fischer 344 rats were given a single oral dose of approx 1 or 8.7 mmol/kg of (14)C-ethylene glycol monomethyl ether. Approx 50 to 60% of the admin (14)C was excreted in urine, and about 12% was eliminated as (14)CO2 within 48 hr.

The uptake of /ethylene glycol monomethyl ether/ (EGME) and the urinary excretion of its major metabolite /methoxyacetic acid/ (MAA) was studied in seven male volunteers during experimental exposure to EGME at rest. The exposure concentration was set at 16 mg/cu m, the present Threshold Limit Value. A high retention (0.76) remained unchanged during the 4-hr exposure period. In combination with a constant pulmonary ventilation and a fixed exposure concentration this resulted in an uptake rate that showed no significant variation in time. The total amount of EGME inhaled corresponded to a dose of only 0.25 mg/kg. During and up to 120 hr after the start of the exposure, MAA was detected in the urine. The elimination half-life was on average 77.1 hr. The total amount of MAA excreted was calculated by extrapolation and averaged 85.5% of the inhaled EGME. ...

...The current study evaluated the metabolism of (14)C-labeled 2ME and the distribution of methoxyacetic acid (MA) in maternal and fetal tissues of pregnant Sprague-Dawley rats either exposed to RF radiation at 10 mHz or sham conditions. Additionally, adduct formation for both plasma and fetal protein was tested as a possible biomarker for the observed 2ME/RF teratogenicity. Rats were administered (ethanol-1,2-(14)C)-2ME (150 mg/kg, 161 uCi/rat average) by gavage on day 13 of gestation immediately before RF radiation body temperature elevation to 42 °C/30 min. Concurrent sham and RF rats were sacrificed at 3, 6, 24 or 48 hr for harvest of maternal blood, urine, fetuses and embryonic fluid. Tissues were either digested for determination of radioactivity or deproteinized with /Trichloroacetic Acid/ (TCA) and analyzed by HPLC for quantification of 2ME metabolites. Results show the presence of 2ME and seven metabolites, with the major metabolite, MA, peaking at 6 hr in the tissues tested. MA, the proximal teratogen, was detectable in maternal serum, urine, fetus and embryonic fluid 48 hr after dosing. Clearance of total body (14)C was significantly reduced for the RF animals (p>0.05) for the 24-48 hr period, but MA values for serum, fetus and embryonic fluid were similar for both sham and RF rats. Additionally, no difference was noted for 2ME metabolite profiles in urine or tissue for sham or RF rats thus eliminating an effect of RF radiation on MA production as a possible explanation for the reported RF/2ME synergism. Subsequently, serum and fetus protein-bound adducts were evaluated by analysis of covalently bound radioactivity. Serum protein binding was significantly higher for sham than RF rats at 3- and 6-hr -- highest for sham rats at 6 hr (519 +/- 95 ug as parent 2ME/g of protein) whereas RF serum values were highest at 24 hr (266 +/- 79 ug/g protein). Fetal protein binding was significantly higher for sham rats at 6 hr, but binding was highest for both groups at

For more Absorption, Distribution and Excretion (Complete) data for 2-METHOXYETHANOL (18 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: 2-Methoxyethanol

Used as a solvent for many different purposes, (e.g., varnishes, dyes, and resins) and as a jet deicing additive; [ACGIH] Used in the Asian microelectronics industry in photoresist formulations and in manufacturing copper-laminate circuit boards; [JOEM 2004;46:707-713]

Semiconductor Manufacturing [Category: Industry];Painting (Solvents) [Category: Paint];Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

For 2-methoxyethanol (USEPA/OPP Pesticide Code: 042202) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The active ingredient is no longer contained in any registered products ... "cancelled."

Solvent for nitrocellulose, ... solvent mixtures, lacquers, ... perfume fixative, ... jet fuel deicing additive.

U.S. Exports · 3 Einträge

(1978) 3.63X10+9 G

(1982) 3.47X10+9 G

(1985) 1.17X10+10 g

U.S. Imports · 3 Einträge

(1978) 2.33X10+8 G

(1982) 2.29X10+8 G

(1985) 2.33X10+8 g

U.S. Production · 6 Einträge

2023: 1,000,000 - <5,000,000 lb;2022: 1,000,000 - <5,000,000 lb;2021: 1,000,000 - <5,000,000 lb;2020: 1,000,000 - <5,000,000 lb

(1978) 5.19X10+10 G

(1982) 4.05X10+10 G

(1985) 3.78X10+10 g

Ethanol, 2-methoxy- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

For more U.S. Production (Complete) data for 2-METHOXYETHANOL (7 total), please visit the HSDB record page.

Consumption Patterns · 1 Eintrag

Jet fuel antiicing additive (military & general aviation aircraft only), 47%; solvent for resins used in the electronics industry, 15%; chemical intermediate, 12%; general solvent & carrier for dyes, 8%; solvent for coatings & inks, 7%; exports, 11% (1983)

Consumer UsesNot Known or Reasonably Ascertainable;Solvent;Fuel agents
Anwendungen · 2 Einträge

Beschreibung2-Methoxyethanol (2-ME), also known as ethylene glycol monomethyl ether, is a glycol ether that has been known since the 1920s, but its use significantly increased in the 1970s. Methoxyethanol is an E-series glycol ether derived from methanol and ethylene oxide. Other commonly used glycol ethers include ethoxyethanol, butoxyethanol, and methoxypropanol.

Verwenden2-Methoxyethanol is considered a non-comedogenic raw material. It is used as a solvent in nail products and as a stabilizer in cosmetic emulsions. It is able to penetrate the skin and may cause skin irritation.

Darstellung

synthetischeFrom Methanol Plus Ethylene glycol, by heating under pressure.

Ergänzende Hinweise

DefinitionChEBI: 2-methoxyethanol is a hydroxyether that is ethanol substituted by a methoxy group at position 2. It has a role as a protic solvent and a solvent.

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