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2-(2-Ethoxyethoxy)ethyl acetate

HCID 8165
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Grundinformationen

CAS
112-15-2
Standard-SMILES
CCOCCOCCOC(C)=O
InChIKey
FPZWZCWUIYYYBU-UHFFFAOYSA-N
Summenformel
C8H16O4
Durchschnittliche Molmasse
176,21 g/mol
Monoisotopische Masse
176,10485899

Überblick

Diethylene glycol ethyl ether acetate is a colorless liquid. (USCG, 1999)

Namen und Bezeichner

Bevorzugter Name
2-(2-Ethoxyethoxy)ethyl acetate
IUPAC
2-(2-ethoxyethoxy)ethyl acetate
Englischer Name
2-(2-Ethoxyethoxy)ethyl acetate
Summenformel
C8H16O4
Molmasse
176.21024

Namen und Synonyme

2-(2-ETHOXYETHOXY)ETHYL ACETATE112-15-2Carbitol acetateDiethylene glycol monoethyl ether acetateEktasolve de acetateEthoxydiglycol acetateKarbitolacetatGlycol ether de acetate2-(2-Ethoxyethoxy)ethanol acetateEthanol, 2-(2-ethoxyethoxy)-, acetateDiglycol monoethyl ether acetateDiethylene glycol ethyl ether acetate
Weitere Namen anzeigen
Karbitolacetat [Czech]Acetic acid 2-(2-ethoxyethoxy)ethyl esterNSC 8702DTXSID6026905HSDB 5555W5EIM81UBXEINECS 203-940-12-(2-Ethoxyethoxy)ethylester kyseliny octove

Datenbank-Bezeichner

CAS
112-15-2
PubChem CID
8165
DTXSID
DTXSID6026905
ChEMBL
CHEMBL3185106
UNII
W5EIM81UBX
EC Number
203-940-1
Nikkaji
J22.125B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,2
Polarare Oberfläche (TPSA)
44,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
8
Schwere Atome
12
Formalladung
0
Komplexität
114

Experimentelle und physikochemische Eigenschaften

SolventsSolvents -> Glycol Ethers (E Series)
CosmeticsSolvent
SpringerMaterials PropertiesBoiling point
OdorCharacteristic: quality: sweet; hedonic tone: pleasant to unpleasant.
TasteBITTER
Density · 4 Einträge

1.0114 at 68 °F (USCG, 1999) - Denser than water; will sink

1.0096 g/cu cm at 20 °C

1.0114

1.0096 @ 20°C

Viscosity0.0279 cP at 20 °C
Color/FormColorless liquid
Solubility · 3 Einträge

Miscible with water, alcohol, ether, most oils

Very soluble in acetone, ethyl ether, ethanol

In water, 1.0X10+6 mg/L at 20 °C /miscible/

Flash Point · 3 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 2.9% (27 of 924) of reports.

Warning

H315 (12.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 924 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Ethanol, 2-(2-ethoxyethoxy)-, acetate

Ethanol, 2-(2-ethoxyethoxy)-, 1-acetate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-(2-ethoxyethoxy)-, 1-acetate 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)

REACH registered substance: 2-(2-ethoxyethoxy)ethyl acetate (EC: 203-940-1)

2-(2-Ethoxyethoxy) ethyl acetate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Ethanol, 2-(2-ethoxyethoxy)-, acetate: Human health tier I assessment
Fire HazardsSpecial Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire. (USCG, 1999)
Fire PotentialCombustible when exposed to heat ...
Health HazardsExposure can cause irritation of eyes, nose and throat. (USCG, 1999)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Tris(2-chloroethyl) phosphate (TRCP) ... produces a dose-, sex-, and species-dependent lesion in the hippocampal region of the brain following subchronic oral administration. This lesion is more common and more severe in female F344 rats than in male F344 rats, and is not observed in B6C3F1 mice. The present investigation of the metabolism of TRCP was designed to detect sex and species variations that might account for differences in toxicity. Elimination of TRCP-derived radioactivity was more rapid in mice, which excreted greater than 70% of an oral dose of 175 mg/kg in urine in 8 hr vs approximately 40% for male or female rats. However, the metabolic profile of TRCP-derived radioactivity in urine was similar for both species. The major metabolite in female rat urine was identified as bis(2-chloroethyl) carboxymethyl phosphate. This metabolite co-chromatographed with the major metabolite found in both male rat and mouse urine. Two additional metabolites identified in female rat urine were bis(2-chloroethyl) hydrogen phosphate and the glucuronide of bis(2-chloroethyl) 2-hydroxyethyl phosphate. These metabolites also cochromatographed with metabolites found in male rat and mouse urine. TRCP metabolism in rats was not induced or inhibited by nine daily 175 mg/kg doses. Toxicity, as evidenced by seizures, was potentiated in male rats pretreated with inhibitors of aldehyde dehydrogenase.

These esters are apparently saponified (eg, hydrolyzed) in the body to the glycol ether (= carbitol) & an organic acid. /Carbitol esters/

Absorption, Distribution and Excretion · 1 Eintrag

The present investigation has examined the metabolism, elimination, and regional brain distribution of (14C)- tris(2-chloroethyl) phosphate (TRCP) in male and female rats. [14C]TRCP was administered by gavage (0, 175, 350, or 700 mg/kg) and urine, feces, exhaled volatiles, CO2, and selected tissues were collected. Regional brain distribution of 14C was determined 2 hr following single doses of TRCP to male and female rats, and 24 hr after a single dose and the last of 14 daily doses of TRCP to female rats. Results of these studies indicate that TRCP is readily absorbed from the gastrointestinal tract, distributed to all brain regions, and that metabolism and excretion are nearly complete in 72 hr. Most of the TRCP-derived radioactivity was excreted in urine (up to 85%), with feces, volatiles, and CO2 combined accounting for less than 10% of the dose. Predominant signs of toxicity associated with TRCP administration (350 and 700 mg/kg) were seizures within 2 hr of treatment, when most of the TRCP-derived radioactivity present in brain tissue was in the form of the parent compound. Traces of inextractable 14C were detected at later times, but this material was not concentrated in brain relative to other tissues.

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230 °F (USCG, 1999)

241 °F (116 °C) OC

230 °F

Boiling Point · 4 Einträge

423.32 °F at 760 mmHg (USCG, 1999)

218.5 °C

423.32 °F

218.5 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits acrid smoke and fumes.

Physikochemische Eigenschaften

Schmelzpunkt
-25 °C · -25 °C
Siedepunkt
218.5 °C · 218.5 °C
Dichte
1.0096 g/cm3 · 1.0096 g/cm3
Hazards SummaryIrritating to skin and eyes; [HSDB] An eye, nose, and throat irritant; [CAMEO] May form explosive peroxides; An irritant; [MSDSonline] See GLYCOL ETHERS.
FDA RequirementsDiethylene glycol monoethyl ether acetate is an indirect food additive for use only as a component of adhesives.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special ReportsOECD; SIDS Initial Assessment Report for SIAM 21. Washington, DC, 18-21 October 2005
TSCA Requirements · 2 Einträge

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethanol, 2-(2-ethoxyethoxy)-, acetate is included on this list. Effective date 9/30/91; Sunset date: 6/30/98.

Reactivity Profile · 1 Eintrag

DIETHYLENE GLYCOL ETHYL ETHER ACETATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

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. Diethylene glycol monoethyl ether acetate is produced, as an intermediate or a final product, by process units covered under this subpart.

Sicherheit und Schutzausrüstung

Fire FightingFire Extinguishing Agents Not to Be Used: Water.
First AidGet medical attention.
Fire Fighting ProceduresTo fight fire, use alcohol foam, water, CO2, dry chemical.
Disposal Methods · 1 Eintrag

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 1 Eintrag

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Protective Action Criteria (PAC) · 3 Einträge

2.2 [mg/m3]

24 [mg/m3]

140 [mg/m3]

Personal Protective Equipment (PPE)Full impervious protective clothing, including boots and gloves. Where splashing is possible wear full face shield or chemical safety goggles. Use approved respirator to protect against vapors. (USCG, 1999)

Toxikologische Informationen

Ecotoxicity ValuesLC50; Species: Pimephales promelas (Flathead minnow, fresh water); Conditions: static bioassay; Concentration: 110 mg/L for 96 hr
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from an assigned value for water solubility of 1X10+6 mg/L (miscible)(2) and a regression-derived equation(3), indicates that diethylene glycol monoethyl ether acetate is expected to have very high mobility in soil(SRC). Volatilization of 2-(2-ethyoxyethoxy)ethyl acetate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 9.89X10-2 mm Hg(4), and assigned value for water solubility(2). Diethylene glycol monoethyl ether acetate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Utilizing the Japanese MITI test, 98-103% of the theoretical BOD was reached over a 4 week incubation period using an activated sludge and an initial chemical concentration of 100 mg/L(5), indicating that biodegradation in soil is an important environmental fate process(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from an assigned value for water solubility of 1X10+6 mg/L (miscible)(2) and a regression-derived equation(3), indicates that diethylene glycol monoethyl ether acetate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.3X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 9.89X10-2 mm Hg(4), and assigned value for water solubility(2). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Estimated hydrolysis half-lives of 300 and 30 days at pHs 7 and 8, respectively(8), suggest that hydrolysis is only expected to be an important process under alkaline conditions(SRC). Utilizing the Japanese MITI test, 98-103% of the theoretical BOD was reached over a 4 week incubation period using an activated sludge and an initial chemical concentration of 100 mg/L(9), indicating that biodegradation in soil is an important environmental fate process(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol monoethyl ether acetate, which has a vapor pressure of 9.89X10-2 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol monoethyl ether acetate 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 13 hours(SRC), calculated from its rate constant of 2.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Diethylene glycol monoethyl ether acetatecontains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Soil Adsorption/Mobility · 1 Eintrag

The Koc of diethylene glycol monoethyl ether acetate is estimated as 10(SRC), using an assigned value for water solubility of 1X10+6 mg/L (miscible)(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethylene glycol monoethyl ether acetate is expected to have very high mobility in soil.

Human Toxicity Excerpts · 4 Einträge

/HUMAN EXPOSURE STUDIES/ Diethylene glycol monoethyl ether acetate (DGEEA) ... produces only a mild irritation when tested on humans.

/SIGNS AND SYMPTOMS/ Human patch tests, using undiluted material, resulted in limited number of people developing mild skin irritation.

/SIGNS AND SYMPTOMS/ Symptomatology: 1. Central nervous depression... 3. Nausea, vomiting, & sometimes diarrhea. 4. ...Headache. Later abdominal & lumbar pain & costovertebral angle tenderness. 5. Transient polyuria & then oliguria, progressing to anuria. 6. Acute renal failure... /Diethylene glycol & its ether-esters/

/SIGNS AND SYMPTOMS/ Symptomatology: 7. Less critical pathological lesions may appear in brain, lungs, liver, meninges & heart. /Diethylene glycol & its ether-esters/

Artificial Pollution SourcesDiethylene glycol monoethyl ether acetate's production and use as a solvent for cellulose esters, gums, resins, coatings and lacquers, and printing inks(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

AEROBIC: Diethylene glycol monoethyl ether acetate, present at 100 mg/L, reached 98 to 103% of its theoretical BOD after 4 weeks using an activated sludge seed at an concentration of 30 mg/L in the Japanese MITI test(1). In a biodegradation study of diethylene glycol monoethyl ether acetate using a settled sewage seed and an initial chemical concentration of 2.5 ppm, diethylene glycol monoethyl ether acetate reached 23.1, 44.0, 82.4, 90.1, 94.6, and 100% of its theoretical BOD after 5, 10, 15, 20, 30, and 40 days, respectively(2). A theoretical BOD of 61% for diethylene glycol monoethyl ether acetate was reached over a period of 10 days in a biodegradation study employing dispersed seed aeration(3).

Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 3 was calculated in fish for diethylene glycol monoethyl ether acetate(SRC), using an estimated log Kow of 0.32(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for diethylene glycol monoethyl ether acetate is estimated as 2.3X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 9.89X10-2 mm Hg(1), and assigned value for water solubility of 1X10+6 mg/L (miscible)(2). This Henry's Law constant indicates that diethylene glycol monoethyl ether acetate is expected to be essentially nonvolatile from water surfaces(3). Diethylene glycol monoethyl ether acetate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Acute Exposure/ Results of an Organization for Economic Cooperation and Development (OECD) Guideline 406 study in guinea pigs indicate that diethylene glycol ethyl ether acetate caused skin irritation but was not sensitizing

/LABORATORY ANIMALS: Acute Exposure/ Undiluted test material (0.1 ml) was placed in the left eye (under the lid) of 6 male small White Russian, Chbb-SPF rabbits. The right eye was the control. Eyes were washed with warm salt water after 72 hours contact with the test material. They were evaluated 1, 24, 72 hours and 6, 8, 10, 13, 17 and 21 days after treatment. The injury was given a grade of 29.4/110. One animal had irreversible damage to the cornea (defined as not recovering to normal after 21 days).The results at 72 hours were described as moderately irritating.

/LABORATORY ANIMALS: Acute Exposure/ Three male, small White Russian rabbits (2.3- 2.7 g) were used in the study. est material (0.5 ml) was applied to the skin, covered with cloth, and wrapped with an elastic bandage. The dressings were removed after 4 hours and the remaining test material was rinsed away with warm water. The skin reaction was scored 1, 24, 48 and 72 hours and 6, 8, and 10 days after removing the dressing. The maximum possible 1) erythema and eschar and 2) edema scores were 4 each. Erythema scores of 1 (very slight) were obtained in 2 animals at 1, 24, and 48 hours. One of these animals also had an erythema score of 1 at 72 hours and 6 days. One animal had an edema score of 1 (very slight) at 1 hour. Edema was not found in at any other time point. The irritation index was 0.67 /8, which was between the values assigned for a designation of slightly irritating (0.6 - 3.0).

/LABORATORY ANIMALS: Acute Exposure/ Rats & guinea pigs exposed to essentially saturated atmospheres at room temperature for 8 hr all survived, but gross autopsy revealed injury to the lungs & kidneys.

/GENOTOXICITY/ In Ames test Salmonella typhimurium TA98, TA100, TA1535, TA1537, TA1538 at 8 - 5000 micrograms/plate, no significant increases in the number of revertant colonies were observed following treatment with the test material, either in the absence or presence of S-9. Test material was not toxic at up to 5000 micrograms/plate.

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of diethylene glycol monoethyl ether acetate with photochemically-produced hydroxyl radicals has been estimated as 2.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.26 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 300 and 30 days at pH values of 7 and 8, respectively(2). Diethylene glycol monoethyl ether acetate contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 1 Eintrag

NIOSH (NOES Survey 1981-1983) has statistically estimated that 18,136 workers (4,675 of these were female) were potentially exposed to diethylene glycol monoethyl ether acetate in the US(1). Occupational exposure to diethylene glycol monoethyl ether acetate may occur through inhalation and dermal contact with this compound at workplaces where diethylene glycol monoethyl ether acetate is produced or used. Use data indicate that the general population may be exposed to diethylene glycol monoethyl ether acetate via dermal contact with products containing diethylene glycol monoethyl ether acetate(SRC).

Regulatorische Informationen

FDA RequirementsDiethylene glycol monoethyl ether acetate is an indirect food additive for use only as a component of adhesives.
TSCA Requirements · 2 Einträge

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethanol, 2-(2-ethoxyethoxy)-, acetate is included on this list. Effective date 9/30/91; Sunset date: 6/30/98.

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. Diethylene glycol monoethyl ether acetate is produced, as an intermediate or a final product, by process units covered under this subpart.

Verwendung und Herstellung

Uses · 4 Einträge

Used as solvent for cellulose esters, gums, resins, coatings, lacquers, and printing inks; [Hawley]

Painting (Solvents) [Category: Paint]

Solvent for cellulose esters, gums, resins; coatings and lacquers; printing inks.

Solvent, eg, for latex paints, lacquers and printing inks

U.S. Production · 5 Einträge

2023: 1,000,000 - <2,500,000 lb

(1979) Probably greater than 4.54X10+6 g

(1981) Probably greater than 4.54X10+6 g

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5432]

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5433]

Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 3 Einträge

Ethylene glycol esters are produced from reaction of ethylene oxide and an appropriate acid and are used also as solvents. Use of a suitable catalyst can influence the outcome of the reaction so as to produce monoesters (sodium acetate) or diesters (sulfuric acid). Glycol monoethers can be converted to the corresponding ether esters by the usual methods. /Ethylene glycol esters/

Produced by esterification of diethylene glycol monoethyl ether.

Reaction of diethylene glycol monoethyl ether with acetic acid

Formulations/PreparationsGrade: Technical
Use ClassificationCosmetics -> Solvent
General Manufacturing Information · 2 Einträge

Not Known or Reasonably Ascertainable

Ethanol, 2-(2-ethoxyethoxy)-, 1-acetate: ACTIVE

Anbieter100 Anbieter

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