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말론산 디에틸
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식별자 및 물리적 특성
| CAS No. | 105-53-3 |
|---|---|
| 분자식 | C7H12O4 |
| 평균 분자량 | 160.17 g/mol |
| 단동위원소 질량 | 160.07355886 g/mol |
| SMILES | CCOC(=O)CC(=O)OCC |
| InChIKey | IYXGSMUGOJNHAZ-UHFFFAOYSA-N |
| PubChem CID | 7761 |
| ChEMBL | CHEMBL177114 |
| ChEBI | CHEBI:167785 |
| EC No. | 203-305-9 |
| DTXSID | DTXSID7021863 |
| 현지명 | 말론산 디에틸 |
화학 및 물리적 성질
| XLogP | 1 |
|---|---|
| 극성 표면적 | 52.6 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 6 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 125 |
| 물질 분류 | Other Classes -> Esters, OtherFlammable agents - 2nd degree |
| 화장품 | Cosmetic ingredients (Diethyl Malonate) -> CIR (Cosmetic Ingredient Review) |
| SpringerMaterials Properties | Boiling point |
| 향료 | Fragrance Ingredient (Diethyl malonate) -> IFRA transparency List |
| LogP(분배 계수) | log Kow = 0.96 |
| 냄새 | Sweet ester odorSlightly aromatic, pleasant odorAroma of ripe fruit, peach, cut grass달콤한 에스테르 냄새 |
| 맛 | Sweet and fruity taste with apple and pineapple nuances |
| 식품 첨가물 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 밀도 | 1.0551 g/cu cm at 20 °CDensity (at 20 °C): 1.06 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.001.053-1.0561.055 @ 20°C1.055 g/mL at 25 °C (lit.) |
| 향미제 | EU Flavoring substances |
| Viscosity | 1.86 centistokes at 25 °C |
| Color/Form | Colorless liquidClear, colorless liquid |
| 녹는점 | -51--50 °C (lit.) |
| 끓는 점 | 199 °C (lit.) |
| 증기 밀도 | 5.52 (vs air) |
| 증기압 | 1 mm Hg ( 40 °C) |
| 굴절률 | n20/D 1.413(lit.) |
| FEMA | 2375 | DIETHYL MALONATE |
| 인화점 | 212 °F |
| 저장 조건 | Store below +30°C. |
| 용해도 | 20.8g/l(외부 MSDS) |
| pKa(산도 계수) | 13.5(at 25℃) |
| 물리적 상태 | 액체 |
| 색상 | 무색 액체 |
| 생물학적 소스 | synthetic |
| 향취 유형 | 과일 같은 |
| 폭발한계 | 0.8-12.8%(V) |
| 용해도 | 에틸알코올, 에테르, 클로로포름, 벤젠과 혼합 가능. 물과 약간 섞임. |
| 비열 | Cp(liquid): 1.78 J/(g·K), at 25℃ |
| Merck | 14,3823 |
| JECFA Number | 614 |
| BRN | 774687 |
| 헨리 상수 | 3.9×100 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 유전율 | 7.9(21℃) |
| 안정성 | 안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다. |
| 주요 응용 | 향료 및 향 |
| 화장품 원료 기능 | 향수 |
| InChI | 1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3 |
| InChIKey | IYXGSMUGOJNHAZ-UHFFFAOYSA-N |
| SMILES | CCOC(=O)CC(=O)OCC |
| LogP(분배 계수) | 0.96 at 20℃ |
| NIST | Propanedioic acid, diethyl ester(105-53-3) |
| EPA | Diethyl malonate (105-53-3) |
화학적 성질
Diethyl malonate has a faint, pleasant, aromatic odor.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 2.7% (69 of 2532) of reports.WarningH319 (96.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)Aggregated GHS information provided per 2532 reports by companies from 18 notifications to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | Chemical: Propanedioic acid, diethyl esterRegulation (EC) No 1831/2003 (amended)Propanedioic acid, 1,3-diethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanedioic acid, 1,3-diethyl 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: 06-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5774Diethyl malonate: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| 화재 위험 | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Heating will cause rise in pressure with risk of bursting. |
| 화재 가능성 | Combustible liquid when exposed to heat or flame. |
| 유해성 요약 | A slight to moderate eye irritant based on animal studies[eChemPortal: SIDSUNEP] A mild skin irritant based on animal studies[MSDSonline] |
| Chemical Dangers | It reacts with strong oxidants. This generates fire and explosion hazard. |
| NFPA Hazard Classification | 1 - Materials that, under emergency conditions, can cause significant irritation.2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Eye Irrit. 2A (96.9%)Flammable liquids - Category 4Flammable agents - 2nd degree |
| Explosive Limits and Potential | Explosive limits , vol% in air: 0.8 - 12.8 |
| Skin, Eye, and Respiratory Irritations | Eye irritation in rabbits: moderately irritating.A skin irritant. |
| Critical Temperature and Pressure | Critical temperature: 653 K (estimated)Critical pressure: 2780 kPa (estimated) |
| Hazardous Reactivities and Incompatibilities | Conditions to avoid: Heat, flames and sparks. Incompatible materials: Acids, Bases, Oxidizing agents, Reducing agentscan react with oxidizing materials. |
| 소화 | Use carbon dioxide, dry powder, water spray, foam. In case of fire: keep drums, etc., cool by spraying with water. |
| 응급 조치 | Fresh air, rest. Seek medical attention if you feel unwell.Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Give one or two glasses of water to drink. Seek medical attention if you feel unwell. |
| 안전 보관 | Separated from strong oxidants. Ventilation along the floor. Store in an area without drain or sewer access. |
| 소화 절차 | Water may be used to blanket fire.To fight fire, use water to blanket fire, foam, CO2, dry chemical.Extinguishing media: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Further information: Use water spray to cool unopened containers. |
| 보관 조건 | Keep container tightly closed in a dry and well-ventilated place. |
| 정리 방법 | ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal. |
| 처리 방법 | SRP: 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product. |
| 누출 처리 | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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. |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | Evaporation at 20 °C is negligiblea nuisance-causing concentration of airborne particles can, however, be reached quickly when dispersed. |
| 상호 작용 | Because it inhibits dehydrochlorinase activity, diethyl malonate (10-40 ppm) increased the toxicity of DDT (2 ppm) to DDT-resistant mosquitoes Culex fatinans. |
| 생태독성 수치 | EC50Species: Pimephales promelas (Fathead Minnow) age 33 days, length 14 mm, weight 0.036 gConditions: freshwater, flow through, 25.4 °C (23.5-27.7 °C), pH 7.42 (7.35-7.45), hardness 44.0 mg/L CaCO3, alkalinity 45.0 mg/L CaCO3, dissolved oxygen 87.6 mg/L (73.7-102 mg/L)Concentration: 20900 ug/L for 24 hrEffect: behavior, loss of equilibrium /99% purity/Concentration: 15600 ug/L for 48 hrLC50Concentration: 23500 ug/L for 24 hr /99% purity/Concentration: 16600 ug/L for 48 hr /99% purity/For more Ecotoxicity Values (Complete) data for Diethyl malonate (7 total), please visit the HSDB record page. |
| 환경 거동 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that diethyl malonate is expected to have very high mobility in soil(SRC). Volatilization of diethyl malonate from moist soil surfaces may occur(SRC) given an estimated Henry's Law constant of 2.0X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.19 mm Hg(3), and water solubility, 2.0X10+4 mg/L(4). In chemical stimulant studies simulating chemical warfare agents, diethyl malonate deposited to dry soil and foliar surfaces was rapidly lost through volatilization processes with observed half-lives on soil of about 2 hours (fast) to 5-16 hours (residual material)(4)foliar half-lives ranged from 1 to 242 hours(5). Two screening studies found diethyl malonate to be readily biodegradable(6,7). An 86% of theoretical BOD in two weeks using activated sludge in the Japanese MITI test(6) suggests that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that diethyl malonate 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 2.0X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.19 mm Hg(4), and water solubility, 2.0X10+4 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 23 and 173 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of 0.96(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Two screening studies found diethyl malonate to be readily biodegradable(8,9). An 86% of theoretical BOD in two weeks using activated sludge in the Japanese MITI test(8) suggests that biodegradation is an important environmental fate process in water(SRC). Diethyl malonate hydrolyzes readily in neutral and alkaline water, but slowly in acidic water(10). Respective hydrolysis half-lives at pH 4, pH7 and pH 9 are <10% after 5 days (50 °C), 137.5 hr (25 °C) and <2.4 hr (50 °C)(10).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethyl malonate, which has a vapor pressure of 0.19 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethyl malonate 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 3.1 days(SRC), calculated from its rate constant of 3.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Diethyl malonate contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| 식품 조사 수치 | Diethyl malonate is reported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy port cider, sherry, and red wine, white and strawberry wines. It is used as a flavor additive in alcoholic beverages, baked goods, frozen dairy, gelatins, puddings, hard candy, non-alcoholic beverages and soft candy(1). |
| 독성 요약 | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgIDENTIFICATION AND USE: Diethyl malonate is used in chemical synthesis. It is also used in food, beverages, and in fragrances. HUMAN STUDIES: A maximization test was reported in 23 volunteers. 4% of the test substance in petrolatum produced no sensitization reactions. Tested at 4% in petrolatum it produced no irritation after a 48-hr closed-patch test on human subjects. ANIMAL STUDIES: Diethyl malonate causes moderate irritation to rabbit's eyes and is non-irritating to rabbit's skin. Application of 0.005 mL of undiluted diethyl malonate to the rabbit cornea caused severe burning. Diethyl malonate fed to rats for 90 days at more than 100 times the equivalent of the human daily dietary intake (averaging 35.93 mg/kg bw per day for males and 41.14 mg/kg bw per day for females) had no adverse effects. The maximum time for inhalation of the concentrated vapor of diethyl malonate by rats without deaths was found to be 8 hr. Mutagenicity test in Salmonella typhimurium TA98, TA 100, TA 1535, TA 1537, TA 1538 was negative with and without activation at concentrations of 8, 40, 200, 1000, 5000 ug/plate 5000 ug/plate (maximal concentration). |
| Average Daily Intake | Diethyl malonate average daily intake = 0.006101 mg/kg/day(1). |
| Signs and Symptoms | Cough.Redness.No acute symptoms expected. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of August 9, 2018: http://actor.epa.gov/dashboard/] |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of diethyl malonate can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that diethyl malonate is expected to have very high mobility in soil(SRC). |
| Natural Pollution Sources | Diethyl malonate is reportedly found in pineapple, bilberry, Cape gooseberrys, grapes and strawberries(1). Diethyl malonate is present in guava fruit, melon, concord grape, pineapple, and blackberry(2). The related diester (dimethyl malonate) occurs in pineapple, bananas and blackberries(3). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Tested at 4% in petrolatum it produced no irritation after a 48-hr closed-patch test on human subjects./HUMAN EXPOSURE STUDIES/ A maximization test was reported in 23 volunteers. 4% of the test substance in petrolatum produced no sensitization reactions. |
| 수질 위해 등급(WGK) | 1 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | OO0700000 |
| 독성 | LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg |
| 관세 코드 | 29171910 |
| 위험 문구(R) | 36/37/38-36 |
| 위험 표시 | Xi |
| 안전 문구(S) | 24/25-26 |
| 기존화학 물질 | KE-29265 |
| 위험 참고 사항 | Irritant |
| 자연 발화 온도 | 435 °C DIN 51794 |
| 위험 등급 | Eye Irrit. 2 |
| 저장 분류 | 10 - Combustible liquids |
| 유해 물질 데이터 | 105-53-3(Hazardous Substances Data) |
용도
용도
그것은 주로 고급 유기 합성에 사용되며 제조 아세트산을 대체합니다. 제약 산업에서 chloroquine, phenylbutazonein, barbital 및 기타 의약품을 합성합니다. 게다가, 그것은 또한 살충제, 페인트, 향신료 및 기타 산업에서 사용할 수 있습니다.
개요
Diethyl malonate is a diester derivative of malonic acid, a dicarboxylic acid with two carboxyl groups (-COO-) separated by one methylene group (-CH2-). Diethyl malonate is formed by the replacement of the hydroxyl groups (-OH) of malonic acid with ethoxy groups (-OCH2CH3). The hydrogen atoms on the methylene carbon between the two carboxyl groups make this compound acidic. Because of its unique structure, diethyl malonate is reactive and functions as a reagent for organic synthesis and to make products such as barbiturates, pigments, and agrochemicals. Volatile esters are known to have fruity scents and are often used as fragrances and flavorings. Diethyl malonate is a volatile diester that occurs naturally in fruits such as grapes, strawberries, guava, melon, pineapple, and blackberries.
출처
Reported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy, port, cider, sherry and red, white, strawberry and bilberry wines.
용도
Diethyl Malonate occurs naturally in grapes and strawberries. It is used in the preparation of barbiturates, artificial flavourings, vitamin B1, and vitamin B6 as well as in perfumes.
일반 설명
Diethyl malonate is diethyl ester of malonic acid. Acylation of diethyl malonate using magnesium chloride and triethylamine is reported. K2CO3-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones.
제조 및 합성 방법
제조 방법
Reacting chloroacetic acid to cyanoacetic acid using sodium cyanide and subsequent saponification; malonic acid is finally esterified by azeotropic distillation with ethanol in benzene