Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
메나디온
비타민K3 · 메나디온 · 2-메틸-1,4-나프탈렌디온 · 메나다이온 · VITAMIN K3 · VITAMIN K · VK3 · 2-METHYL-1,4-NAPHTHOQUINONE
식별자 및 물리적 특성
| CAS No. | 34524-96-4 |
|---|---|
| 분자식 | C11H8O2 |
| 평균 분자량 | 172.18 g/mol |
| 단동위원소 질량 | 172.05242949 g/mol |
| SMILES | CC1=CC(=O)c2ccccc2C1=O |
| InChIKey | MJVAVZPDRWSRRC-UHFFFAOYSA-N |
| PubChem CID | 4055 |
| ChEMBL | CHEMBL590 |
| ChEBI | CHEBI:28869 |
| EC No. | 200-372-6 |
| DTXSID | DTXSID4021715 |
| 현지명 | 메나디온 |
화학 및 물리적 성질
| XLogP | 2.2 |
|---|---|
| 극성 표면적 | 34.1 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 13 |
| 형식 전하 | 0 |
| 복잡도 | 288 |
| pH | Alc soln is neutral to litmus |
| LogP(분배 계수) | 2.2log Kow = 2.20 @ pH 7.4 |
| LogS | -3.03 |
| 냄새 | Very faint acrid odorNearly odorless약간의 냄새 |
| Color/Form | Bright yellow crystalsYELLOW NEEDLES FROM ALC, PETROLEUM ETHER |
| 용해도 | 160Slightly soluble in ethanol, acetic acid, and ligroin. Soluble in ethyl ether, benzene, chloroform, and sulfuric acid.One gram dissolves in about 60 ml alcohol, in 10 ml benzene, in 50 ml vegetable oilsmoderately soluble in chloroform, carbon tetrachloride.Soluble in aromatic solventsSOL IN FATSFor more Solubility (Complete) data for MENADIONE (6 total), please visit the HSDB record page.기름: 용해성 |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| 녹는점 | 107105-107 °C105-107 °C(lit.) |
| 증기압 | 0.000188 [mmHg] |
| Physical Description | Bright yellow solid with a very mild acrid odor[Merck Index] |
| Stability/Shelf Life | Stable in airdecomp by sunlight. ... Destroyed by alkalies and reducing agents.STABLE IN QUINONE FORM.Solns may be heated to 120 °C without decomp. |
| Kovats Retention Index | 1496.1259.23 |
| 끓는 점 | 262.49°C (rough estimate) |
| 밀도 | 1.1153 (rough estimate) |
| 굴절률 | 1.5500 (estimate) |
| 저장 조건 | room temp |
| 물리적 상태 | 수정 같은 |
| 색상 | 노란색 |
| 생물학적 소스 | synthetic (organic) |
| 용해도 | 불용성 |
| Merck | 14,5831 |
| BRN | 1908453 |
| 헨리 상수 | 3.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 안정성 | 안정적인. 빛에 민감할 수 있습니다. 강한 산화제와 호환되지 않습니다. |
| 주요 응용 | 의약품(소분자) |
| 화장품 원료 기능 | 향기 |
| InChI | 1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 |
| InChIKey | MJVAVZPDRWSRRC-UHFFFAOYSA-N |
| SMILES | CC1=CC(=O)c2ccccc2C1=O |
| LogP(분배 계수) | 2.200 |
| NIST | Menadione(58-27-5) |
| EPA | Menadione (58-27-5) |
화학적 성질
Bright-yellow crystals with a very faint acrid odour. Insoluble in water; soluble in benzene (1 g/10 mL), ethanol (1 g/60 mL), and vegetable oils (1g/50 mL); moderately soluble in carbon tetrachloride and chloroform. Stable in air; decomposed by sunlight; destroyed by alkalis and reducing agents.
안전 및 규제
| GHS 분류 | WarningH302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (95.3%): Causes skin irritation [Warning Skin corrosion/irritation]H317 (63.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (98.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H400 (70.5%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410 (64.7%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 190 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 규제 정보 | Chemical: 1,4-Naphthalenedione, 2-methyl-Status: Active Update: 27-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/26040Menadione: Does not have an individual approval but may be used under an appropriate group standard |
| 유해성 요약 | A skin and mucous membrane irritant[HSDB] May cause hemolytic anemia and cellular damage[IARC] A skin and strong eye irritantA possible sensitizerHarmful by ingestionTargets the kidney, liver, and blood[Sigma-Aldrich MSDS] See 1,2-Naphthoquinone. |
| FDA 요건 | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products. Menadione is included on this list. |
| Hazard Classes and Categories | Acute Tox. 4 (97.4%)Skin Irrit. 2 (95.3%)Skin Sens. 1 (63.7%)Eye Irrit. 2 (100%)STOT SE 3 (98.4%)Aquatic Acute 1 (70.5%)Aquatic Chronic 1 (64.7%) |
| Skin, Eye, and Respiratory Irritations | Irritant to the skin and mucous membranes, especially the alcoholic solution. |
| 보관 조건 | Keep protected from light. |
| 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. |
| 상호 작용 | Large doses of salicylates... antagonize vitamin k. ... Cmpd with ... antagonist activity is sulfaquinoxaline, a sulfonamide drug used in veterinary medicine... . /vitamin k/Vitamin k antagonizes inhibitory effect of /acenocoumarol, phenprocoumon, anisindione, diphenadione, and phenindione/ on hepatic synthesis of vitamin k dependent clotting proteins... . /vitamin k/ |
| 생태독성 수치 | LC50 Pimephales promelas 0.11 mg/l (4 days) /Conditions of bioassay not specified/ |
| 환경 거동 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 370(SRC), determined from a log Kow of 2.20(2) and a regression-derived equation(3), indicates that menadione is expected to have moderate mobility in soil(SRC). Volatilization of menadione from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Menadione is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-4 mm Hg(SRC), determined from a fragment constant method(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 370(SRC), determined from a log Kow of 2.20(2) and a regression-derived equation(3), indicates that menadione is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.1X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1.4(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), menadione, which has an estimated vapor pressure of 1.9X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in the vapor phase in the ambient atmosphere. Vapor-phase menadione 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 33 hrs(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Menadione is decomposed by sunlight(4). |
| 노출 경로 | Variable and ranges from 10% to 80% |
| 독성 요약 | Menadione (vitamin K3) is involved as a cofactor in the posttranslational gamma-carboxylation of glutamic acid residues of certain proteins in the body. These proteins include the vitamin K-dependent coagulation factors II (prothrombin), VII (proconvertin), IX (Christmas factor), X (Stuart factor), protein C, protein S, protein Zv and a growth-arrest-specific factor (Gas6). In contrast to the other vitamin K-dependent proteins in the blood coagulation cascade, protein C and protein S serve anticoagulant roles. The two vitamin K-dependent proteins found in bone are osteocalcin, also known as bone G1a (gamma-carboxyglutamate) protein or BGP, and the matrix G1a protein or MGP. Gamma-carboxylation is catalyzed by the vitamin K-dependent gamma-carboxylases. The reduced form of vitamin K, vitamin K hydroquinone, is the actual cofactor for the gamma-carboxylases. Proteins containing gamma-carboxyglutamate are called G1a proteins. |
| 생태독성 발췌 | /PLANTS/ Vitamin K and its analogs are fungistatic against wide variety of fungi. /Vitamin K/ |
| Signs and Symptoms | Menadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage. |
| Soil Adsorption/Mobility | The Koc of menadione is estimated as 370(SRC), using a log Kow of 2.20(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that menadione is expected to have moderate mobility in soil. |
| Atmospheric Concentrations | URBAN/SUBURBAN: Menadione was tested for but not detected in urban air samples collected in Leeds, UK, date not specified(1). |
| Artificial Pollution Sources | Menadione's production and use in medicines and animal feed additives(1) may result in its release to the environment through various waste streams(SRC). Its former production and use in fungicides(1) may have resulted in its direct release to the environment(SRC). |
| Carcinogen Classification | 3, not classifiable as to its carcinogenicity to humans. (L135) |
| Environmental Bioconcentration | An estimated BCF of 1.4 was calculated for menadione(SRC), using a log Kow of 2.20(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). |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | QL9100000 |
| 독성 | LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson) |
| 관세 코드 | 29147000 |
| 위험 문구(R) | 22-36/37/38-43 |
| 위험 표시 | Xn,Xi |
| 안전 문구(S) | 26-36-37/39-24 |
| 위험 등급 | IRRITANTAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| F 고인화성물질 | 8 |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 58-27-5(Hazardous Substances Data) |
| 함량 및 규제정보 | 물질구분: 유독물질혼합물(제품)함량정보: 2-메틸-1,4-나프탈렌디온 및 이를 25% 이상 함유한 혼합물 |
| 유해화학물질 필터링 | 2018-1-835(신규화학물질) |
용도
개요
Vitamin K is a general term referring to a group of naphthoquinone derivatives required in the diet for blood clotting. Menadione is a fat-soluble vitamin that is essential for blood clotting. It is destroyed by irradiation during processing but has no appreciable loss during storage. It occurs in spinach, cabbage, liver, and wheat bran.
용도
Menadione is precursor to verious types of Vitamin K. It is of industrial importance as an intermediate in the synthesis of phylloquinone, and salts of its bisulfite adduct are used as stabilized forms in the animal feed industry. Commercially significant forms are menadione sodium bisulfite and menadione dimethyl pyrimidinol. Used as a micronutrient for livestock and pet foods.
일반 설명
Menadione is a prothrombogenic compound and belongs to the Vitamin K class of compounds, which are necessary for the biosynthesis of prothrombin and other blood clotting factors. It is used as a model quinone in cell culture and in vivo investigations. It is obtained as a catabolic product of phylloquinone and circulating precursor of tissue menaquinone-4 in rats.
제조 및 합성 방법
제조 방법
Menadione can be prepared by oxidizing 2-methylnaphthalene with chromic acid or hydrogen peroxide.