HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Menadion
VITAMIN K3 · VITAMIN K · VK3 · 2-METHYL-1,4-NAPHTHOQUINONE · Menadion · Aquinone · 2-METHYL-1,4-NAPHTHAQUINONE · Aquakay
Identifikatoren & physikalische Daten
| CAS No. | 34524-96-4 |
|---|---|
| Summenformel | C11H8O2 |
| Durchschnittliche Molmasse | 172,18 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | Menadion |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 34,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 288 |
| pH | Alc soln is neutral to litmus |
| LogP (Verteilungskoeffizient) | 2.2log Kow = 2.20 @ pH 7.4 |
| LogS | -3.03 |
| Geruch | Very faint acrid odorNearly odorless |
| Color/Form | Bright yellow crystalsYELLOW NEEDLES FROM ALC, PETROLEUM ETHER |
| Löslichkeit | 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.oil: solubleINSOLUBLE |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 107105-107 °C105-107 °C(lit.) |
| Dampfdruck | 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 |
| Siedepunkt | 262.49°C (rough estimate) |
| Dichte | 1.1153 (rough estimate) |
| Brechungsindex | 1.5500 (estimate) |
| Lagerbedingungen | room temp |
| Aggregatzustand | crystalline |
| Farbe | yellow |
| Geruch | Slight odor |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,5831 |
| BRN | 1908453 |
| Henry-Konstante | 3.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. May be light sensitive. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | pharmaceutical (small molecule) |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCE |
| 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 (Verteilungskoeffizient) | 2.200 |
| CAS Datenbank | 58-27-5(CAS DataBase Reference) |
| NIST chemische Informationen | Menadione(58-27-5) |
| EPA chemische Informationen | Menadione (58-27-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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. |
|---|---|
| Regulatorische Informationen | 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 |
| Gefahrenübersicht | 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-Anforderungen | 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. |
| Lagerbedingungen | Keep protected from light. |
| Entsorgungsverfahren | 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. |
| Wechselwirkungen | 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/ |
| Ökotoxizitätswerte | LC50 Pimephales promelas 0.11 mg/l (4 days) /Conditions of bioassay not specified/ |
| Umweltverhalten | 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). |
| Expositionspfade | Variable and ranges from 10% to 80% |
| Toxizitätsübersicht | 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. |
| Ökotoxizitätsauszüge | /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). |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29147000 |
| RTECS-Nr. | QL9100000 |
| R-Sätze (R) | 22-36/37/38-43 |
| Toxizität | LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson) |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 26-36-37/39-24 |
| Gefahrenklasse | IRRITANTAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 58-27-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.
Herstellung & Synthese
synthetische
Menadione can be prepared by oxidizing 2-methylnaphthalene with chromic acid or hydrogen peroxide.