메틸아크릴레이트-D6

Methyl Acrylate

HCID 178796309CAS 71016-31-4

기본 정보

표준 SMILES
C=CC(=O)OC
InChIKey
BAPJBEWLBFYGME-UHFFFAOYSA-N
분자식
C4H6O2
평균 분자량
86.09 g/mol

개요

Methyl acrylate can cause cancer according to California Labor Code and the World Health Organization's International Agency for Research on Cancer (IARC).

이름 및 식별자

우선 이름
Methyl Acrylate
IUPAC
methyl prop-2-enoate
현지명
메틸아크릴레이트-D6
영어명
Methyl acrylate-d6
분자식
C4H6O2
분자량
86.09

이름 및 동의어

METHYL ACRYLATE96-33-3Methyl prop-2-enoate2-Propenoic acid, methyl esterMethyl propenoateMethyl 2-propenoateMethylacrylaatMetilacrilatoMethyl-acrylatMethoxycarbonylethyleneAcrylic acid, methyl esterAcrylate de methyle
이름 더 보기
메틸아크릴레이트-D6Methyl acrylate-d6Methyl Acrylate-d6 (stabilized with hydroquinone)
Curithane 103AcrylsaeuremethylesterMethyl propenateMethylester kyseliny akrylove2-propenoic acid methyl esterDTXSID0024183WC487PR91HNSC-24146

데이터베이스 식별자

CAS
71016-31-4
ChEMBL
CHEMBL9019
ChEBI
CHEBI:82482
UNII
WC487PR91H
EC Number
202-500-6
Nikkaji
J3.967E

물성

구조 계산 물성

XLogP
0.8
극성 표면적
26.3 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
2
무거운 원자 수
6

실험 및 물리화학적 성질

Chemical Classes · 2건

Flammable agents - 3rd degree

Volatile Organic Compound (VOC)

PolymersPlastics & Rubber -> (Meth)acrylates
CosmeticsFilm forming
SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS
LogP · 4건

log Kow = 0.80

0.80

0.8

0.74

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1195) of reports.

Danger

H225 (> 99.9%): Highly Flammable liquid and vapor [Danger Flammable liquids]

유해성 정보

Regulatory Information · 6건

Chemical: 2-Propenoic acid, methyl ester

Hazard Traits - Carcinogenicity

Regulation (EC) No 1935/2004 (amended)

2-Propenoic acid, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, methyl ester 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)

Status: Active Update: 11-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15313

2-Propenoic acid, methyl ester: HSNO Approval: HSR001189 Approved with controls

Other Safety InformationIMAP assessments - 2-Propenoic acid, methyl ester: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 3건

Special Hazards of Combustion Products: Irritating vapors are generated in fires.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Vapour/air mixtures are explosive.

Fire Potential · 2건

Flammable and combustible liquid

Dangerously flammable when exposed to heat, flame, or oxidizers.

Health Hazards · 2건

May irritate skin, eyes, respiratory system, and gastro- intestinal tract. Fumes cause tears. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious); polymerization hazard]:

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

First Aid Measures · 4건

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. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2건

· 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.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3건

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.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. See Chemical Dangers. Cooled. Keep in the dark. Well closed. Store only if stabilized.
Firefighting HazardsVapors are heavier than air and may travel to a source of ignition and flash back. Liquid floats on water and may travel to a source of ignition and spread fire. /Methyl acrylate, inhibited/

독성 정보

Interactions · 1건

Pretreatment of rats with triorthotolyl phosphate potentiated the lethal action of inhaled methyl and ethyl acrylate. Carboxylesterases are important in detoxification of methyl and ethyl acrylate and the exposure to inhibitors of carboxylesterase may potentiate the adverse effects of acrylate esters.

Target OrgansEyes, skin, respiratory system
Ecotoxicity Values · 3건

EC50; Species: Chlorococcales (Green algae order); Conditions: freshwater, static; Concentration: 55.0 mg/L for 24 hr; Effect: physiology, assimilation efficiency /formulation/

EC50; Species: Pseudokirchneriella subcapitata (Green algae) age 3-7 days; Conditions: freshwater, static, 24 °C, pH 6.3-9.3; Concentration: 15.53 mg/L for 96 hr (95% confidence interval: 0-46.78 mg/L); Effect: decreased population biomass

EC50; Species: Pseudokirchneriella subcapitata (Green algae, age 3-7 days); Conditions: freshwater, static, 24 °C, pH 7.19-9.05; Concentration: 18.57 mg/L for 96 hr (95% confidence interval: 3.74-33.41 mg/L); Effect: decreased population biomass

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a structure estimation method(2), indicates that methyl acrylate is expected to have very high mobility in soil(SRC). Volatilization of methyl acrylate from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 2.0X10-4 atm-cu m/mole(SRC) based upon its vapor pressure, 86.6 mm Hg(3), and water solubility, 49,400 mg/L(4). Methyl acrylate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Utilizing the Japanese MITI test, 37% of the Theoretical BOD was reached in 2 weeks indicating that biodegradation is an important environmental fate process in soil(5). The degradation rate of methyl acrylate in soil was 3.0X10-7/s based on calculations using a chemical pollution footprint methodology(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a structure estimation method(2), indicates that methyl acrylate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.0X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 86.6 mm Hg(4), and water solubility, 49,400 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 hours and 5 days, respectively(SRC). Hydrolysis half-lives of 8.5 and 0.85 years at pH values of 7 and 8, respectively, were estimated for methyl acrylate(2). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of 0.80(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Utilizing the Japanese MITI test, 37% of the Theoretical BOD was reached in 2 weeks indicating that biodegradation is an important environmental fate process in water(8). Degradation rates of methyl acrylate in water and sediment were 6.0X10-7/s and 6.6X10-8/s, respectively, based on calculations using a chemical pollution footprint methodology(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl acrylate, which has a vapor pressure of 86.6 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl acrylate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, ozone and nitrate radicals(SRC); the half-lives for these reactions in air are estimated to be 30 hours, 11 days and 334 days(SRC), calculated from its respective rate constants of 1.3X10-11, 1.05X10-18 and 1.0X10-16 cu cm/molecule-sec at 25 °C(3). Methyl acrylate contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). The degradation rate of methyl acrylate in air was 7.8X10-6/s based on calculations using a chemical pollution footprint methodology(5).

Food Survey ValuesMethyl acrylate has been reported to be a volatile component of pineapple concentrate(1).
Adverse EffectsDermatotoxin - Skin burns.

규제 정보

FDA RequirementsHomopolymers and copolymers of methyl acrylate are an indirect food additive for use only as a component of adhesives.
State Drinking Water Guidelines(FL) FLORIDA 210 ug/L

화학 및 산업

약리 정보

Metabolism/Metabolites · 5건

Conjugation with sulfhydryl groups appears to be an important detoxification process for methyl acrylate in the guinea-pig. The thioethers were identified as N-acetyl-S-(2- carboxyethyl)-L-cysteine and the corresponding monomethyl ester, with a ratio between the two metabolites of 20:1. In male rats exposed to methyl acrylate by inhalation, depletion of nonprotein sulfhydryl compounds was most pronounced in the lung, compared to liver, kidney and blood. After administration of methyl acrylate to Wistar rats, no hydroxymercapturic acid that might be derived from the epoxide of methyl acrylate was detected. It seems unlikely, therefore, that epoxidation of the acrylic esters occurs in vivo

/Researchers/ studied the biotransformation of methyl acrylate in rats. The total amount of thioesters in urine was low, with increased levels of two mercapturic acids (2-carboethylmercapturic and 2 alkoxycarbonyl ethyl mercapturic acids); this suggests the presence of unidentified sulfur-containing metabolites. These observation confirm findings of /another study/ that rats administered methyl acrylate intraperitoneally 5 days/week for 3 weeks produced significant amounts of mercapturic acids in urine; this was postulated to be due to a Michael-type reaction, such that during the biotransformation of methyl acrylate, glutathione is added to the ethylene group.

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity.

Methylacrylate is hydrolyzed to acrylic acid in rat liver, kidney, and lung homogenates. Disappearance in blood in vitro could be due at least in part to binding with nonprotein sulfhydryls in RBC rather than to hydrolysis.

For more Metabolism/Metabolites (Complete) data for Methyl acrylate (7 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 5건

It is readily absorbed by mucous membranes and through the intact skin.

Whole-body autoradiology was performed in the guinea pigs with 2,3-(14)C-labeled methyl acrylate. 2,3-(14)C-methyl acrylate quickly disappeared from guinea pigs after oral and, somewhat slower, after ip admin. After admin in a closed cup on skin a slow penetration in dermis occurred. Internal organs showed a slow rise in radioactivity.

Organ damage was observed in test animals when they were exposed to methyl and ethyl acrylate and methyl methacrylate vapors. This shows that acrylate compounds are absorbed from the lungs. Ethyl acrylate vapor was efficiently absorbed from the lungs of the rat (63% on an average); the proportion retained was the same at different concentration levels up to 1000 mg/cu m.

When guinea pigs were given radioactively labeled methyl acrylate intraperitoneally, about 35% of the dose was excreted in expired air as carbon dioxide in 3 days; the main part during the first few hours. Almost an equal proportion of the given dose was excreted in urine as thioethers in 3 days after administration.

For more Absorption, Distribution and Excretion (Complete) data for Methyl acrylate (10 total), please visit the HSDB record page.

Cellular LocationsCytoplasm

용도 및 제조

Uses · 6건

Acrylates and methacrylates are monomers that are combined with other monomers or polymers to produce plastics used in cosmetics, medicine, dentistry, and manufacturing industries. [Marks, p. 181] Workers in dental and surgical laboratories may be exposed; Used as a comonomer with acrylonitrile to produce acrylic and modacrylic fibers to make clothing and home furnishings; Also used to prepare paperboard, thermoplastic coatings, adhesives, sealants, surfactants, medical and dental prostheses, contact lenses, latex coatings, fabric finishes, and resins for purification of industrial effluents; [ACGIH]

Pulp and Paper Processing [Category: Industry]

Primary use is production of acrylic and modacrylic fibers; used as a comonomer with acrylonitrile in such fibers.

Methyl acrylate has been used in the preparation of thermoplastic coating, adhesives, sealants, and amphoteric surfactants for shampoos. It is used to produce medical and dental prostheses, contact lenses, and other specialty plastics such as latex coatings and floor and fabric finishes. It can serve as a resin in the purification of industrial effluents or aid in the timed release and disintegration of pesticides.

In dental, medical, and pharmaceutical sciences; utilized as monomer, polymer, or copolymer; as microencapsulation mixture component or for polymerization of radioactive waste; as resin in purification and decolorization of industrial effluents or aid in timed release and disintegration of pesticides.

The monomer in manufacturing leather finish resins, textile and paper coatings, and plastic films. Produces the hardest resin of the acrylate ester series.

ImpuritiesWater content-0.1% (max), acid content as acrylic acid-0.01% (max)
U.S. Exports(1972) 1.29 X 10+10 g
U.S. Imports · 3건

(1972) 4.54 X 10+7 g

(1975) 2.8 X 10+6 g

(1983) 1.36 X 10+9 g /Acrylates & Acrylic Acid/

U.S. Production · 6건

2023: 100,000,000 - <500,000,000 lb

(1972) 1.73 X 10+10 g

(1976) 2.04 X 10+10 g

2-Propenoic acid, methyl ester 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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#746]

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

Consumption Patterns · 4건

(All acrylate esters, of which n-butyl acetate is the largest volume): surface coatings 44%; adhesives/sealants 18%; textiles 15%, plastics additives 9%, paper 5%, other 9% (2000)

(All acrylic acid esters) 46% as a monomer for emulsion polymers and solution polymers in latex paints; 26% as a monomer for emulsion polymers in textile applications; 6% as a comonomer for acrylic fibers; 6% as a monomer for emulsion polymers in polishes; 6% as a monomer for emulsion polymers in paper applications; 4% as a monomer for emulsion polymers used in base coatings and surface impregnation of natural leather; 6% in misc applications (1973)

47% for surface coatings; 22% for textiles; 7% for paper; 7% for polishes; 3% for leather; 9% for acrylic fibers; and 5% for misc applications (1969) /All acrylic esters/

45% for coatings, 16% for textiles and leather finishes, 9% for paper coatings, 8% for adhesives, 6% for polyacrylates, 5% for polishes, 5% for acrylic fibers, 6% other (1983 est) /Acrylates and acrylic acid/

응용 분야

용도Methyl Acrylate-d6 (CAS# 71016-31-4) is a useful isotopically labeled research compound.

공급사4 곳

盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
成都思天德生物科技有限公司028-83243028 19136088901 · [email protected]
Clearsynth Labs Limited+91-22-26355700 · [email protected]

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