Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
메틸티오글라이콜레이트
메틸티오글라이콜레이트 · Methyl 2-mercaptoacetate · MTG · THIOGLYCOLIC ACID METHYL ESTER · METHYL MERCAPTOACETATE · Methyl sulfanylacetate · METG · methyl2-mercaptoacetate
식별자 및 물리적 특성
| CAS No. | 2365-48-2 |
|---|---|
| 분자식 | C3H6O2S |
| 평균 분자량 | 106.15 g/mol |
| 단동위원소 질량 | 106.00885043 g/mol |
| SMILES | COC(=O)CS |
| InChIKey | MKIJJIMOAABWGF-UHFFFAOYSA-N |
| PubChem CID | 16907 |
| ChEMBL | CHEMBL1341329 |
| EC No. | 219-121-7 |
| DTXSID | DTXSID0033673 |
| 현지명 | 메틸티오글라이콜레이트 |
화학 및 물리적 성질
| XLogP | 0.4 |
|---|---|
| 극성 표면적 | 27.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 6 |
| 형식 전하 | 0 |
| 복잡도 | 52.8 |
| 물질 분류 | Other Classes -> Thioglycolates |
| 화장품 | Cosmetic ingredients (Methyl Thioglycolate) -> CIR (Cosmetic Ingredient Review)Hair waving or straightening |
| SpringerMaterials Properties | Schoenflies notation |
| 끓는 점 | 148 °C42-43 °C/10 mmHg (lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of sulfoxides. |
| Physical Description | Colorless liquid with a stench[MSDSonline] |
| Dissociation Constants | pKa= 8.08 @ 25 °C |
| 녹는점 | -24 °C |
| 밀도 | 1.187 g/mL at 25 °C (lit.) |
| 굴절률 | n20/D 1.466(lit.) |
| 인화점 | 86 °F |
| 저장 조건 | Store below +30°C. |
| 용해도 | 40g/L |
| 물리적 상태 | 액체 |
| pKa(산도 계수) | 8.04±0.10(Predicted) |
| 색상 | 무색의 |
| 냄새 | Strong, unpleasant, garlic-like |
| 용해도 | 40g/L(20℃) |
| BRN | 506259 |
| 헨리 상수 | 1.6×100 mol/(m3Pa) at 25℃, HSDB (2015) |
| 화장품 원료 기능 | 헤어 웨이브 또는 스트레이트 |
| InChI | 1S/C3H6O2S/c1-5-3(4)2-6/h6H,2H2,1H3 |
| InChIKey | MKIJJIMOAABWGF-UHFFFAOYSA-N |
| SMILES | COC(=O)CS |
| NIST | Acetic acid, mercapto-, methyl ester(2365-48-2) |
| EPA | Acetic acid, mercapto-, methyl ester (2365-48-2) |
화학적 성질
CLEAR COLOURLESS LIQUID
안전 및 규제
| GHS 분류 | DangerH226 (72.2%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P272, P280, P301+P316, 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)Aggregated GHS information provided per 90 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| 규제 정보 | Chemical: Acetic acid, mercapto-, methyl esterStatus: Active Update: 22-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/18423Methyl thioglycolate: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | IMAP assessments - Acetic acid, mercapto-, methyl ester: Human health tier II assessment |
| 유해성 요약 | Causes somnolence and tremor in lethal-dose studies of rats[RTECS] An irritantToxic if swallowedMay be harmful by inhalation or skin absorption[MSDSonline] |
| Hazard Classes and Categories | Flam. Liq. 3 (72.2%)Specific target organ toxicity (repeated exposure) - category 2 |
| 처리 방법 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 환경 거동 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6.4(SRC), determined from a structure estimation method(2), indicates that methyl thioglycolate is expected to have very high mobility in soil(SRC). Volatilization of the undissociated form of methyl thioglycolate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.22X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, a pKa of 8.08(5) indicates methyl thioglycolate will exist mostly in the ionized form at pH values above 8 and therefore at these pHs, volatilization from moist surfaces is not expected to be an important fate process. The potential for volatilization of methyl thioglycolate from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 7.5 mm Hg(SRC), determined from a fragment constant method(4).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6.4(SRC), determined from an estimation method(2), indicates that methyl thioglycolate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6.22X10-6 atm-cu m/mole(SRC) for the unionized form, 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 4 and 48 days, respectively(SRC). A pKa of 8.08(8) indicates methyl thioglycolate will exist mostly in the ionized form at pH values above 8 and therefore volatilization from water surfaces at these pHs is not expected to be an important fate process. According to a classification scheme(5), an estimated BCF of 3.1(SRC), from an estimated log Kow of 0.32(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl thioglycolate, which has an estimated vapor pressure of 7.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl thioglycolate 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 3.5X10-13 cu cm/molecule-sec at 25 °C, determined using a structure estimation method(3). |
| 유해 작용 | Neurotoxin - Other CNS neurotoxin |
| 독성 요약 | Based on the available data, the CIR Expert Panel concluded that ... Methyl Thioglycolate is safe for use in hair straighteners, permanent waves, tonics, dressings, and so forth, wave sets, other non-coloring hair products, and hair dyes and colors, as described in this safety assessment, at concentrations up to 15.2% (as Thioglycolic Acid). Hairdressers should avoid skin contact and minimize consumer skin exposure.Safe for use in cosmetics, with qualifications |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl thioglycolate can be estimated to be 6.4(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl thioglycolate is expected to have very high mobility in soil. The pKa of methyl thioglycolate is 8.08(3), indicating that this compound will exist in the dissociated form in the environment at basic conditions and anions generally do not adsorb to organic carbon and clay more strongly than their neutral counterparts. |
| TSCA Test Submissions | Methyl mercaptoacetate (CAS # 2365-48-2) was evaluated for acute dermal toxicity in guinea pigs (strain unspecified) administered occluded applications (dosage, volume unspecified) to depilated abdominal skin for 24 hours. Treatment was associated with signs of "moderate" dermal irritation in 2/2 animals including slight to moderate erythema and edema, necrosis at 24 hours, and scars at 14 days post-exposure. In 6 guinea pigs, unspecified dermal doses administered by the same method produced mortality (4/6) consistent with a dermal LD50 of 0.5-1 ml/kg. No further information regarding method or results was provided.Methyl mercaptoacetate (CAS # 2365-48-2) was evaluated for subchronic oral toxicity in groups of 5 male rats (strain unspecified) fed 10, 100, and 300 mg/kg doses in corn oil by oral gavage on 5 days/week over a period of 15 days (11 treatments). After 2 doses of 300 mg/kg, 3/5 rats died, while the remaining 2 were sacrificed due to poor body condition. Clinical signs of toxicity included dehydration, hypoactivity, weakness, hypothermia, and poor body condition. No overt toxicity was noted among rats receiving 10 or 100 mg/kg doses, save a solitary 100 mg/kg male which exhibited transient inactivity after an initial dose only. In 100 mg/kg rats, the rate of weight gain during Days 1-4 and the terminal mean weight gain were significantly lower than those of controls. The 2 sacrificed rats of 300 mg/kg doses demonstrated depressed white cell and glucose levels, while aspartate aminotransferase, alanine aminotransferase, lactic dehydrogenase, and urea nitrogen values were elevated. Both hematological and clinical chemistry values were comparable to those of controls in rats fed 100 mg/kg doses. Upon necropsy of 300 mg/kg rats, gross lesions included hemorrhagic stomachs, unilateral testicular atrophy, adipose atrophy, discolored liver and spleen, and corneal opacity. Cellular changes were characterized by thymic lymphocytic necrosis, lipoid degeneration, hypertrophic hepatocytes and nuclear changes in the liverglomerular casts, cytoplasmic vacuolization, and degeneration of the proximal convoluted tubules in the kidneyserous atrophy of adipose tissuedegenerated spermatids or atrophied seminiferous epithelium of the testicle, and degenerated spermatids in the epididymis. Terminal necropsy of lower dosed rats identified only eosinophilic cytoplasmic changes in the liver at 100 mg/kg (4/5). Rats dosed with 10 mg/kg showed no toxicity by the criteria and methods of this study. |
| Artificial Pollution Sources | Methyl thioglycolate's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | An estimated BCF of 3.2 was calculated for methyl thioglycolate(SRC), using an estimated log Kow of 0.32(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low. |
| Volatilization from Water/Soil | The Henry's Law constant for methyl thioglycolate is estimated as 6.22X10-6 atm-cu m/mole(SRC) for the undissociated form using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl thioglycolate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 48 days(SRC). A pKa of 8.08(4) indicates methyl thioglycolate will exist mostly in the ionized form at pH values above 8 and therefore volatilization from water surfaces at these pHs is not expected to be an important fate process. Methyl thioglycolate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of methyl thioglycolate from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 7.5 mm Hg(SRC), determined from a fragment constant method(3). |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of methyl thioglycolate with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-13 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). A base-catalyzed second-order hydrolysis rate constant of 1.7 L/mole-sec(SRC) was estimated using a structure estimation method(2)this corresponds to half-lives of 48 and 5 days at pH values of 7 and 8, respectively(2). Methyl thioglycolate is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm). |
| Probable Routes of Human Exposure | Occupational exposure to methyl thioglycolate may occur through inhalation at workplaces where methyl thioglycolate is produced or used. (SRC) |
| Environmental Fate/Exposure Summary | Methyl thioglycolate's production and use as chemical intermediate may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 7.5 mm Hg at 25 °C indicates methyl thioglycolate will exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl thioglycolate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicalsthe half-life for this reaction in air is estimated to be 11 hrs. If released to soil, methyl thioglycolate is expected to have very high mobility based upon an estimated Koc of 6.4. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 6.22X10-6 atm-cu m/mole for the undissociated form. The pKa of methyl thioglycolate is 8.08 indicating that this compound will exist in the dissociated form in the environment at basic conditions and anions generally do not adsorb to organic carbon and clay more strongly than their neutral counterparts. Methyl thioglycolate may volatilize from dry soil surfaces based upon its vapor pressure. If released into water, methyl thioglycolate is not expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. A pKa of 8.08 indicates methyl thioglycolate will exist mostly in the ionized form at pH values above 8 and therefore at these pHs, volatilization from water surfaces is not expected to be an important fate process. Estimated volatilization half-lives for a model river and model lake are 4 and 48 days, respectively. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to methyl thioglycolate may occur through inhalation of this compound at workplaces where methyl thioglycolate is produced or used. (SRC) |
| Non-Human Toxicity Values | LD50 Rat oral 209 mg/kgLD50 Rat ip 252 mg/kgLD50 Mouse ip 100 mg/kg |
| 수질 위해 등급(WGK) | 1 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | AI7350000 |
| 운송 번호(UN) | UN 1992 3/PG 3 |
| 독성 | mouse,LD50,intraperitoneal,100mg/kg (100mg/kg),National Technical Information Service. Vol. AD277-689, |
| 관세 코드 | 29309070 |
| 위험 문구(R) | 10-20/22-36/37/38-25 |
| 위험 표시 | Xn,T |
| 안전 문구(S) | 26-36/37-45-36/37/39-28A |
| 포장분류 | III |
| 위험 등급 | 3Acute Tox. 3 OralAcute Tox. 4 InhalationEye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3 |
| 저장 분류 | 3 - Flammable liquids |
| 유해 물질 데이터 | 2365-48-2(Hazardous Substances Data) |
용도
용도
Methyl Thioglycolate is an derivative of Thioglycolic Acid (T350760), an organic compound containing both a thiol and a carboxylic acid functional groups. Thioglycolic Acid and its derivatives are oft en used in organic synthesis as a nucleophile in thioglycolysis reactions and is also used as a S transfer agent for sulfonyl chloride synthesis. Methyl Thioglycolate have been studied for the its inf luence on neocarzinostatin activation and expression of DNA damage.
일반 설명
Methyl thioglycolate reacts with nonprotein component of the antitumor antibiotic neocarzinostatin to form 1:1 adduct. It reacts with isothiocyanate to form Rhodanine.
제조 및 합성 방법
생산 방법
Adding thioglycollic acid with purity of between 70.0 and 96.0 percent and methanol with purity of between 95.0 and 99.9 percent into a reaction device according to the molar ratio of 1:1.3-4.0; subsequently, adding an activating agent into the reaction device, stirring and heating for reaction; and after the reaction is finished, carrying out separatory distillation on reaction products to obtain the methyl thioglycolate. The activating agent is a p-toluenesulfonic acid methanol solution with a mass concentration of between 20 and 30 percent, and the use amount is 0.5 to 1.0 percent of the total mass of relative input materials.