메탄술폰산에틸에스테르

Ethyl Methanesulfonate

HCID 6113CAS 62-50-0

기본 정보

표준 SMILES
CCOS(C)(=O)=O
InChIKey
PLUBXMRUUVWRLT-UHFFFAOYSA-N
분자식
C3H8O3S
평균 분자량
124.16 g/mol
단동위원소 질량
124.01941512

개요

Ethyl Methanesulfonate can cause cancer according to an independent committee of scientific and health experts.

이름 및 식별자

우선 이름
Ethyl Methanesulfonate
IUPAC
ethyl methanesulfonate
현지명
메탄술폰산에틸에스테르
영어명
Ethyl methanesulfonate
분자식
C3H8O3S
분자량
124.16

이름 및 동의어

ETHYL METHANESULFONATE62-50-0Ethyl mesylateEthyl methanesulphonateHalf-myleranMethanesulfonic acid, ethyl esterethylmethanesulfonateEthyl methansulphonateMethylsulfonic acid, ethyl esterNSC 26805Ethyl ester of methylsulfonic acidEthyl ester of methanesulfonic acid
이름 더 보기
메탄술폰산에틸에스테르에틸메테인설포네이트에틸 메테인설포네이트EMSMETHANESULFONIC ACID ETHYL ESTERCB 1528ethylesterofmethylsulfonicacidethylesterofmethanesulfonicacidethylesterofmethylsulphonicacidethylesterofmethanesulphonicacid
Methanesulphonic acid ethyl esterEthyl ester of methylsulphonic acidEthyl ester of methanesulphonic acidENT 26396DTXSID6025309Ethylester kyseliny methansulfonoveEthyl methansulfonate9H154DI0UP

데이터베이스 식별자

CAS
62-50-0
PubChem CID
6113
DTXSID
DTXSID6025309
ChEMBL
CHEMBL338686
ChEBI
CHEBI:23994
UNII
9H154DI0UP
EC Number
200-536-7
Nikkaji
J1.927E

물성

구조 계산 물성

XLogP
0
극성 표면적
51.8 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
2
무거운 원자 수
7

실험 및 물리화학적 성질

Chemical Classes · 2건

Other Classes -> Sulfur Compounds

Carcinogens

Density · 3건

1.1452 at 72 °F (NTP, 1992) - Denser than water; will sink

Specific gravity: 1.1452 at 22 °C/4 °C

1.1452 @ 22°C

Color/FormColorless liquid
Solubility50 to 100 mg/mL at 81 °F (NTP, 1992)
Flash Point212 °F (NTP, 1992)
Boiling Point · 3건

415 to 416 °F at 761 mmHg (NTP, 1992)

213-213.5 °C at 761 mm Hg

213 °C @760 [mm Hg]

물리화학적 성질

녹는점
25 °C · <25 °C
끓는 점
85 · 85-86 °C/10 mmHg (lit.)
밀도
1.206 g/mL · 1.206 g/mL at 20 °C
증기압
0.27 hPa · 0.27 hPa (25 °C)
굴절률
20 · n20/D 1.418(lit.)
인화점
100 °C · 100 °C

화학적 성질

colourless liquid

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Danger

유해성 정보

Regulatory Information · 6건

Chemical: Methanesulfonic acid, ethyl ester

Hazard Traits - Carcinogenicity

Regulation (EC) No 1107/2009 (amended)

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

Ethyl methanesulphonate: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Methanesulfonic acid, ethyl ester: Human health tier I assessment
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health Hazards · 1건

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, respiratory tract and mucous membranes, dermatitis, nausea, vomiting, central nervous system depression and fibrosis. It may cause decreased visual acuity. A related compound is corrosive to tissues.

Hazards Summary · 2건

A mutagen, tumorigen, and reproductive effector; [RTECS] A skin, eye, and mucous membrane irritant; May cause CNS depression; [CAMEO] An alkylating agent and developmental toxicant; [REPROTOX] An irritant; [MSDSonline]

The major hazards encountered in the use and handling of ethyl methanesulfonate stem from its toxicologic properties. Exposure to this colorless liquid may occur from its use as a mutagen in experimental biochemical research. Effects from exposure may include mutagenesis. Also, the International Agency for Research on Cancer (IARC) has designated ethyl methanesulfonate as a Group 2B carcinogen, meaning, "The agent is possibly carcinogenic to humans." Exhaust ventilation which employs a high-efficiency particulate arrestor (HEPA) or charcoal filter should be used to minimize airborne levels of this substance. In activities and situations where over-exposure may occur, wear a protective suit and a carefully fitted respiratory. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes and wash exposed skin thoroughly with soap and water. Smoking, eating, and drinking should be prohibited in ethyl methanesulfonate work areas. Ethyl methanesulfonate should be stored in a securely sealed container which is enclosed in a second, unbreakable, leakproof container. Ethyl methanesulfonate is a potential candidate for fluidized bed, rotary kiln, and liquid injection forms of incineration.

Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

안전 및 보호

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1건

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.

Storage Conditions · 1건

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Cleanup Methods · 1건

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal. ... The plastic bag should be sealed immediately. ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated. ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, 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 60-70% ethanol followed by washing with a 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.

Disposal Methods · 5건

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U197, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for ETHYL METHANESULFONATE (8 total), please visit the HSDB record page.

독성 정보

Interactions · 5건

The antimutagenic effects of vitamins C, E, and A, and derivatives of vitamin C on ethyl methanesulfonate induced 6TG resistant mutations in Chinese hamster V79 cells were examined. Vitamin C was most effective in inhibiting ethyl methanesulfonate cytotoxicity and 6TG resistant mutations. In the presence of vitamin C at a concentration of 100 micrograms/ml, ethyl methanesulfonate induced mutations were reduced to about one-third or one-forth of those in control cultures treated with ethyl methanesulfonate alone. Dehydro-vitamin C and iso-vitamin C also inhibited ethyl methanesulfonate induced mutations to about ... one-half or one-third of the control level. ... Vitamin C may react directly with ethyl methanesulfonate as a desmutagen and thus inactivate its mutation-inducing activity in Chinese hamster V79 cells. Vitamin E had an additive cytotoxic effect on EMS-induced cytotoxicity. This vitamin enhanced the frequencies of 6TG-resistant mutations induced by ethyl methanesulfonate. Pretreatment with vitamin E before treatment with ethyl methanesulfonate resulted in no detectable effect in modifying the ethyl methanesulfonate induced mutations. On the contrary, vitamin A markedly enhanced ethyl methanesulfonate induced mutation frequencies.

The 1,4-dihydropyridine derivative 2,6-dimethyl-3,5-diethoxycarbonyl-4-(sodium carboxylate)-1,4-dihydropyridine was studied for antimutagenic effect in the dominant lethal test and in the sex-linked recessive lethal test of Drosophila melanogaster. ... 1,4-dihydropyridine reduces the frequency of ethyl methanesulfate induced genetic damage (point mutations and chromosome breakage). A reduction of the mutation rate induced by ethyl methanesulfate in adults could be observed independently of the developmental stages (larvae or imago) pretreated with 1,4-dihydropyridine. The protective effect of this ... antimutagen against the alkylating agent depended on both the 1,4-dihydropyridine dose and the level of the ethyl methanesulfonate induced mutation rate. The effect of 1,4-dihydropyridine was more pronounced than that of /cysteine and cysteamine/.

Rat and canine hepatocyte suspensions were exposed to toxic concentrations of ethyl methanesulfonate (EMS) and ionophore A-23187 in the presence and absence of extracellular calcium (Ca2+) and alpha-tocopheryl succinate (alpha-TS). The exogenous administration of alpha-TS (25 microM) completely protected hepatocytes from chemically- induced toxicity when exposed to physiological free extracellular calcium concentrations (0.8-1.5 mM). ... Hepatocytes exposed to unesterified alpha- tocopherol (alpha-T, 25 microM) or alpha-tocopheryl acetate (alpha-TA, 25 microM), however, were not protected from the toxic effect of chemicals even though these treatments resulted in the marked accumulation of cellular alpha-T (2.65 nml/10(6) cells) and alpha-TA (2.3 nmol/10(6) cells), respectively. Finding suggest that the supplementation of endogenous stores of alpha-T or alpha-TA does not promote protection against chemical toxicity and that alpha-TS cytoprotection results not from the accumulation of alpha-T but rather from the cellular presence of the intact alpha-TS molecule. Thus alpha-TS appears to possess cytoprotective properties that differ from other vitamin E congeners.

The combination of EMS and aureomycin was highly cytotoxic, but EMS alone inhibited the mitosis in Vicia fabia.

For more Interactions (Complete) data for ETHYL METHANESULFONATE (7 total), please visit the HSDB record page.

Ecotoxicity Values · 2건

EC50; Species: Oryzias latipes (Medaka, high-eyes, embryo 66 hr postfertilization); Conditions: freshwater, static, 20 °C; Concentration: 66 mmol/L for 2 hr (95% confidence interval: 59.5-66.6 mmol/L); Effect: growth, abnormal

LC50; Species: Oryzias latipes (Medaka, high-eyes, embryo 66 hr postfertilization); Conditions: freshwater, static, 20 °C; Concentration: 72 mmol/L for 2 hr (95% confidence interval: 66.1-78.5 mmol/L)

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a structure estimation method(2), indicates that ethyl methanesulfonate is expected to have very high mobility in soil(SRC). Volatilization of ethyl methanesulfonate from moist soil surfaces may occur(SRC) given an estimated Henry's Law constant of 5.4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, hydrolysis of ethyl methanesulfonate is expected to be the major fate process in moist soil based on measured half-lives in water of 46(5) and 96 hours(6). Ethyl methanesulfonate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.206 mm Hg(4). Biodegradation data were not available(SRC, 2007).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a structure estimation method(2), indicates that ethyl methanesulfonate 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 5.4X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 and 60 days, respectively(SRC). However, the rapid hydrolysis of ethyl methanesulfonate, with half-lives of 46(8) and 96 hours(9), indicates that hydrolysis, and not volatilization, will be the major fate process for this compound in aquatic environments. According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.2(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl methanesulfonate, which has a vapor pressure of 0.206 mm Hg at 25 °C (2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl methanesulfonate 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 17 days(SRC), calculated from its rate constant of 9.6X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Ethyl methanesulfonate 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 EffectsNeurotoxin - Other CNS neurotoxin
Ecotoxicity Excerpts · 2건

/AQUATIC SPECIES/ The filamentous blue-green algae, Anabaena oryzae and Nostoc entophytum, were isolated from rice fields soil and clonal cultures were raised from a single filament. 10 mL suspensions of both algae were treated with 0.1 mL ethyl methanesulfonate (EMS) for 0, 15, 30 and 60 min. Observations were made for 14 days. EMS progressively decreased the fresh weight of Anabaena oryzae (except on 2nd day at 15 min time dose) over controls. Chlorophyll a decreased in all the days with increase in dose time. In Nostoc entophytum, growth rates in EMS treated cultures were significantly affected but the cells grew after a long lag-phase (as compared to controls). Chlorophyll a was consistently reduced (except on 4th and 6th day at 15 min time dose) over controls. Vegetative cell length and breadth for both algae were higher in treated cultures. Algae treated with 0.1 mL of EMS at pH 5 for 2 hr, grew after a much shorter lag phase than those treated at higher pH values (pH 6, 7, or 8). Breakage of filaments and cell lysis were observed in Anabaena oryzae at 30 and 60 min doses. Nostoc entophytum was even more strongly affected. The cells showed chlorosis and lysis with incr time doses. The filaments in control were greenish blue whereas in treated samples they were pale yellow.

/BIRDS and MAMMALS/ Juvenile Coturnix coturnix japonica males were injected intravenous with 2, 20 or 200 mg ethyl methanesulfonate/kg bw; and hematologic variables were measured at 0 (non-injected), 24 and 72 hr post-injection. Ethyl methanesulfate induced hemolytic anemia began within 24 hr post-injection. Recovery from anemia began within 72 hr post-injection of ethyl methanesulfate. Ethyl methanesulfate induced lymphocytopenia, monocytopenia and heterophilia. The anemia induced by ethyl methanesulfate was dissimilar from that induced by phenylhydrazine and that EMS affected leukopoiesis.

Effluent Concentrations · 1건

Tire leachate water, obtained from tire cores exposed to water for 40 days, did not contain ethyl methanesulfonate at concentrations greater than the detection limit of 1.0 ug/L(1). Ethyl methanesulfonate was not detected in four process waste streams (sweet syngas, turbine stack gas, incinerator stack gas, offgas from wastewater treatment) from the Dow syngas facility in Plaquemine, LA during 1991(2).

규제 정보

RCRA Requirements · 1건

U119; As stipulated in 40 CFR 261.33, when ethyl methanesulfonate as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802; The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
PB2100000
ridadr
2810
HS 번호
29041000
risk_code
46-22-40-36/37/38-45

화학 및 산업

약리 정보

Mechanism of Action · 1건

/GENOTOXICITY/ The relative importance of different sites of alkylation on DNA was determined by comparing two ethylating agents. 1-Ethyl-1-nitrosourea ethylates DNA with a higher proportion of total adducts on ring oxygens than ethyl methanesulfonate, which ethylates with a higher proportion of total adducts on the N-7 of guanine. ... To determine the importance in germ-line mutagenesis of the O6-G site relative to the N-7 of guanine, dose-response curves were constructed for both 1-ethyl-1-nitrosourea and ethyl methanesulfonate, where dose was measured as total adducts per deoxynucleotide and response as sex-linked recessive lethals induced in Drosophila melanogaster spermatozoa. For both mutagens the dose response curve was linear and extrapolated to the origin. ... 1-Ethyl-1-nitrosourea is 1.9 times more efficient per adduct in inducing sex-linked recessive lethals mutations than EMS. In vitro studies showed that 1-ethyl-1-nitrosourea induced 9.5% of its total adducts on O6-G while EMS induced 2.0% of its adducts on O6-G. If O6-G was the sole genotoxic site, then 1-ethyl-1-nitrosourea should be 4.8 times more efficient per adduct than ethyl methanesulfonate. ... While O6-G was the principal genotoxic site, N-7 G made a significant contribution to germ-line mutagenesis.

Biological Half-Life... HALF-LIFE IN RAT BLOOD SERUM ... 6.5 HR.
Metabolism/Metabolites... IS METAB ... BY REACTION WITH GLUTATHIONE TO GIVE ETHYLMERCAPTURIC ACID, & BY HYDROLYSIS TO ETHANOL ... .
MeSH Pharmacological Classification · 2건

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026)

Absorption, Distribution and Excretion... Is rapidly distributed in the mammalian system and increases the excretion of methylnicotinamide.

용도 및 제조

Uses · 4건

Used as experimental mutagen, teratogen, and brain carcinogen; [Merck Index]

BIOCHEMICAL RESEARCH

Experimentally as mutagen, teratogen and brain carcinogen.

... As catalysts for esterification, polymerizarion, and alkylation, and for the production of peroxycarboxylic acids from hydrogen peroxide and carboxylic acids. /Lower molecular mass alkanesulfonic acids/

U.S. Production · 2건

(1975) NOT PRODUCED COMMERCIALLY IN USA.

(1977) NOT PRODUCED COMMERCIALLY IN USA.

Methods of ManufacturingREACTION OF METHANESULFONIC ANHYDRIDE WITH ETHYL ALCOHOL.
General Manufacturing Information · 2건

Methanesulfonic acid, ethyl ester: ACTIVE

REVERSIBLE MALE CHEMOSTERILANT FOR INSECTS & MAMMALIAN PESTS. /MONOESTERS OF METHANESULFONIC ACID/

응용 분야

용도Ethyl methanesulfonate is used as mutagen for both mammalian and plant cells. It finds application as a model alkylating agent in the study of deoxyribonucleic acid (DNA) repair processes.

일반 설명Clear colorless liquid. Denser than water.

공급사50 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]

추가 설명

정의ChEBI: A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.

관련 반응

15건

연결된 노트

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