2186-24-5Cc1ccc(OCC2CO2)cc1CUFXMPWHOWYNSO-UHFFFAOYSA-NCresyl glycidyl ether is a colorless liquid. Sinks and mixes with water. (USCG, 1999)
1.09 at 68 °F (USCG, 1999) - Denser than water; will sink
1.14 at 25 °C
less than 200 °F (NTP, 1992)
200 °F (Open Cup)
498 °F at 760 mmHg (approx.) (USCG, 1999)
170 to 195 °C at 100 mbar
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Warning
H315: Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P272, P273, P280, P302+P352, P318, P321, P332+P317, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Warning
H315: Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P272, P273, P280, P302+P352, P318, P321, P332+P317, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.
Cresyl glycidyl ether: Does not have an individual approval but may be used under an appropriate group standard
A skin and eye irritant; May cause skin sensitization; [HSDB] Forms explosive peroxides in air; A skin and eye irritant; May cause skin sensitization; [CAMEO] A skin irritant; May cause skin sensitization; [eChemPortal: ERMA; ESIS] An strong irritant; May cause skin sensitization; [MSDSonline] See o-Cresyl glycidyl ether and m-Cresyl glycidyl ether. See GLYCIDYL ETHERS.
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importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, ((methylphenoxy)methyl)- is included on this list.
o-Cresyl glycidyl ether was converted rapidly to the corresponding diol compounds when incubated with guinea pig liver homogenate in vitro. /o-Cresyl glycidyl ether/
Studies in preparations of microsomal and cytosolic fractions of liver and lung derived from human, rat, and mouse showed that o-cresyl glycidyl ether is a good substrate for glutathione tranferase, with mice being the most efficient in enzymatic glutathione conjugation. Overall, enzymatic hydrolysis of the epoxide group is the most important route of in vitro biotransformation of o-cresyl glycidyl ether, with the highest activity located in the microsomes. Human samples generally had a higher efficiency for hydrolysis than mice or rats. /o-Cresyl glycidyl ether/
The urinary metabolite profile of o-cresyl glycidyl ether in rats, following ip administration of single doses up to 164 mg/kg, indicated that glutathione (GSH) conjugation and epoxide hydrolysis were key biotransformation pathways of o-cresyl glycidyl ether. At low dose levels GSH conjugation and epoxide hydrolysis accounted each for about 25% of urinary metabolites; however at higher doses epoxide hydrolysis became the most prominent route of detoxification (40%). /o-Cresyl glycidyl ether/
The urinary metabolite profiles of phenyl-glycidyl-ether (PGE) and its structural analogue ortho-cresyl-glycidyl-ether (oCGE) were determined in male Wistar-rats. Quantitative analytical methods were used to investigate the metabolites of PGE and oCGE, their dose excretion relationships and urinary excretion kinetics. Rats were dosed intraperitoneally with PGE or oCGE in doses ranging from 0.033 to 1.0 mmol/kg. ...Rats treated with oCGE excreted oCGEMA, COLA, and NAPS, showing that the metabolite profiles of PGE and oCGE were comparable. The quantitative methods developed to determine the urinary mercapturic-acid metabolites of PGE and oCGE offered enough selectivity and sensitivity for their determination as low as 0.033mmol/kg. The authors conclude the method can be used for humans with low potential exposures. Human excretion of lactic-acid and the novel serine metabolites of these glycidyl ethers should be further investigated, as possible inactivation of these epoxides may be by epoxide hydrolysis mediated routes.
... During skin penetration, all GE were extensively metabolized to their corresponding (bis-)diols. Virtually no YX4000, and only very small amounts of C12GE and BADGE, penetrated the skin unchanged, but significant amounts of HDDGE and o-CGE penetrated the skin unchanged. For o-CGE, but none of the other GE, the percentage of the applied dose that penetrated the skin unchanged increased over time. The large variation in response observed with the five selected GE indicates that GE should not be considered as a single class of compounds but rather on the basis of their individual properties.
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2186-24-5、26447-14-3DTXSID3024863CHEMBL3249573Cresyl glycidyl ether is a colorless liquid. Sinks and mixes with water. (USCG, 1999)
Clear colorless liquid; [HSDB]
colourless liquid
A phenol and epoxide. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.
Skin Irrit. 2 (99.7%)
Germ cell mutagenicity - category 2
Skin irritation - category 2
Skin corrosion/irritation - Category 2
Skin corrosion/irritation - Category 2
Muta. 2
Contact with skin and eyes causes irritation.
/Glycidyl ethers/ are primary skin and eye irritants and may cause sensitization. /Glycidyl ethers/
/Cresyl glycidyl ether and o-cresyl glycidyl ether/ are moderate to severe skin irritants and potent skin sensitizers ... slightly irritating to the eye.
Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl & diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl & diglycidyl ethers/
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.
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
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.
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.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 67(SRC), determined from a structure estimation method(2), indicates that cresyl glycidyl ether is expected to have high mobility in soil(SRC). Volatilization of cresyl glycidyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.6X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(4) through neutral, acid, or base-mediated reactions(5). Cresyl glycidyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-2 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2006).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 67(SRC), determined from a structure estimation method(2), indicates that cresyl glycidyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important environmental fate process(3) based upon an estimated Henry's Law constant of 7.6X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 9(SRC), from an estimated log Kow of 2.2(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(7) through neutral, acid, or base-mediated reactions(8). Hydrolysis products are usually the corresponding diol and sometimes re-arranged products(8). While data specific to cresyl glycidyl ether were not located(SRC, 2006), the hydrolysis half-life for an analogous compound glycidyl alcohol is 28 days at pH 7(7). Biodegradation data were not available(SRC, 2006). However, a 33% theoretical BOD using the Japanese MITI test for analogous phenyl glycidyl ether(9) suggests that biodegradation of cresyl glycidyl ether may occur in aquatic environments(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cresyl glycidyl ether, which has an estimated vapor pressure of 4.3X10-2 mm Hg at 25deg C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cresyl glycidyl ether is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 11 hrs(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of cresyl glycidyl ether can be estimated to be 67(SRC). According to a classification scheme(2), this estimated Koc value suggests that cresyl glycidyl ether is expected to have high mobility in soil.
/HUMAN EXPOSURE STUDIES/ Epoxy resin systems (ERSs) are a frequent cause of occupational allergic contact dermatitis. Sensitization occurs not only to the resins, but also to hardeners and reactive diluents. However, only a fraction of the ERS components currently in use are available for patch testing. With the multicentre study EPOX 2002, we attempted to improve diagnostics in this field by patch testing with components currently used in ERSs. During the first study period (October 2002 to July 2003), in addition to commercially available ERS patch test substances, 16 study substances (1 resin, 9 hardeners and 6 reactive diluents) were patch tested in 70 patients with suspected contact allergy due to ERSs and 22 patients with a prior positive patch test reaction to epoxy resin (ER) in the standard series. Most frequently, allergic reactions to ER based on diglycidyl ether of bisphenol A and F were observed (55.2% and 43.7%, respectively). Agreement between positive reactions to both resins, which can be explained by immunological cross-sensitization and/or coexposure, was substantial [Cohen's kappa 0.65 (95% CI: 0.49-0.80)]. Among the reactive diluents, 1,6-hexanediol diglycidyl ether (1,6-HDDGE) and 1,4-butanediol diglycidyl ether (1,4-BDDGE) were the most frequent allergens, with 19.5% and 18.4% positive reactions, respectively. Although agreement between positive reactions to 1,6-HDDGE and 1,4-BDDGE was even better than with the 2 resins, the sample size is considered too small to decide reliably whether 1,6-HDDGE alone could serve as a marker allergen for both. Allergic reactions to p-tert-butylphenyl glycidyl ether and to phenyl glycidyl ether (PGE) occurred in 11.5% of the patients tested, with only moderate agreement. All patients positive to cresyl glycidyl ether (6.8%) also reacted to PGE. Of the hardeners tested, m-xylylene diamine was the most frequent allergen (13.8%), followed by isophorone diamine (5.7%). No reactions were observed to several substances, the test concentration of which may have been too low and will be increased in the future.
/SIGNS AND SYMPTOMS/ Cresyl glycidyl ether is a mild irritant and may cause dermatitis.
/SIGNS AND SYMPTOMS/ Cresyl glycidyl ether and o-cresyl glycidyl ether are potent skin sensitizers in humans.
/CASE REPORTS/ A case of contact urticaria due to epoxy resin and reactive diluents was described. A 23 year old male with a 6 month history of pruritis and urticarial weals on the face and upper limbs, occasionally accompanied by angioderma of the lips and tongue, and transient laryngeal constriction was evaluated. He reported being employed for 2 years as a part fitter in an aircraft factory where he was regularly exposed to epoxy products and solvents such as naphtha (8030306) and 1,1,1-trichloroethane (71556). His symptoms would develop within 20 minutes of exposure to epoxy compounds and were worse when he was working within a closed section of fuselage. The symptoms resolved within about 2 hours after exposure ended. Patch testing was performed with the European standard allergen series and epoxy, acrylate, isocyanates, and plastics and glues series. The patient was also tested with a special series of 15 epoxy compounds, hardeners, and solvents which he used at work. The patches were read after 30 minutes and 4 days. Urticarial reactions were observed after 30 minutes to epoxy resin and the reactive diluents phenylglycidyl-ether (122601) and cresylglycidyl-ether (26447143). No delayed reactions were seen at the 4 day reading. The patient agreed to be retested with the three substances. Retesting produced similar urticarial lesions, which were also accompanied by pharyngeal tingling and hoarseness. Oral treatment with 10 milligrams loratadine (79794755) cleared the lesions within 60 minutes. The author notes that contact urticaria caused by epoxy compounds has been infrequently reported. However, this is the first reported case of contact urticaria being caused by reactive diluents.
AEROBIC: Biodegradation data for cresyl glycidyl ether were not available(SRC, 2006). However, a 33% theoretical BOD using the Japanese MITI test for analogous phenyl glycidyl ether(1) suggests that biodegradation of cresyl glycidyl ether may occur in aquatic environments(SRC).
An estimated BCF of 9 was calculated for cresyl glycidyl ether(SRC), using an estimated log Kow of 2.2(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).
The Henry's Law constant for cresyl glycidyl ether is estimated as 7.6X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that cresyl glycidyl ether is not expected to volatilize from water surfaces(2). Cresyl glycidyl ether's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Cresyl glycidyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-2 mm Hg(SRC), determined from a fragment constant method(3).
/LABORATORY ANIMALS: Acute Exposure/ Undiluted o-Cresyl glycidyl ether produced severe skin irritation at 24 hr, which progressed to necrosis by 14 days. Following a 4-hr semioccluded exposure o-cresyl glycidyl ether caused slight irritation to the skin with a complete recovery of the irritant effects within 7 days. /o-Cresyl glycidyl ether/
/LABORATORY ANIMALS: Acute Exposure/ Signs of /acute oral/ toxicity /in rats/ included dyspnea and lacrimation, and congested liver was observed at necropsy ...
/LABORATORY ANIMALS: Acute Exposure/ Signs of intoxication /in rats/ were ataxia and general depression. Dermal exposure resulted in severe dermal irritation. /o-Cresyl glycidyl ether/
/LABORATORY ANIMALS: Acute Exposure/ /Cresyl glycidyl ether/ is a moderate skin irritant in rabbits ...
For more Non-Human Toxicity Excerpts (Complete) data for CRESYL GLYCIDYL ETHER (21 total), please visit the HSDB record page.
The rate constant for the vapor-phase reaction of cresyl glycidyl ether with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC), using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Glycidyl ethers, such as cresyl glycidyl ether, can react readily with water and with nucleophiles such as proteins and nucleic acids(2). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(3) through neutral, acid, or base-mediated reactions(4). Hydrolysis products are usually the corresponding diol and sometimes re-arranged products(4). While data specific to cresyl glycidyl ether were not located(SRC, 2006), the hydrolysis half-life for an analogous compound glycidyl alcohol is 28 days at pH 7(3).
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. Oxirane, ((methylphenoxy)methyl)- is included on this list.
In vitro skin penetration studies with dermatomized human and rat skin and whole mouse skin indicated that o-cresyl glycidyl ether has a potential to penetrate the skin. Permeability was in the order: mouse>rat>human. o-Cresyl glycidyl ether is rapidly hydrolyzed after penetration into the skin; however, a minimum of 10% of the applied dose may be present as unchanged material after absorption through the skin. /o-Cresyl glycidyl ether/
Glycidyl ethers (GE), an important class of industrial chemicals, are considered to be potentially mutagenic in vivo because some GE have been shown to be direct mutagens in short-term in vitro tests. The percutaneous penetration and metabolism of representatives of different classes of GE was studied in the fresh, full-thickness C3H mouse, and dermatomed human and Fisher 344 rat skin to determine the apparent permeability constants, lag times and metabolic profiles. Five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabelled analogues were synthesized with a 14C-label using [U-14C]-epichlorohydrin. There was a large variation (four orders of magnitude) in percutaneous penetration between the five GE. In general, penetration through full-thickness mouse skin was higher than through dermatomed rat skin, whereas dermatomed human skin was the least permeable. The permeability increased in the order YX4000 < BADGE < C12GE < o-CGE < HDDGE. The relative skin permeability of the five GE could be explained for a significant part by the lipophilicity, expressed as log P(o/w), in combination with the molecular weight of the compounds.
Used as a reactive diluent for epoxy resin systems; [HSDB]
Plastic Composites Manufacturing [Category: Industry]
..As a reactive diluent for viscosity reduction of liquid epoxy resin systems, to increase the level of filler loading of such systems, and to reduce the tendency of the resins to crystallize
(1986) 10 thousand-500 thousand pounds[US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Oxirane,
(1994) 10 thousand-500 thousand pounds[US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Oxirane,
(1998) 10 thousand-500 thousand pounds[US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Oxirane,
개요Cresyl glycidyl ether is a reactive diluent added in epoxy res ins of the Bisphenol A type.
일반 설명Colorless liquid. Sinks and mixes with water.
For more Human Toxicity Excerpts (Complete) data for CRESYL GLYCIDYL ETHER (7 total), please visit the HSDB record page.