ビタミン K3
2-メチル-1,4-ナフトキノン · カレオン · ビタミンK3 · カッパキシン · 2-メチルナフタレン-1,4-ジオン · パノシン · プロカイビット · カノン
識別子と物理属性
| CAS No. | 34524-96-4 |
|---|---|
| 分子式 | C11H8O2 |
| 平均分子量 | 172.18 g/mol |
| 単同位体質量 | 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 |
| 現地名 | ビタミン K3 |
化学・物理的性質
| XLogP | 2.2 |
|---|---|
| 極性表面積 | 34.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 288 |
| pH | Alc soln is neutral to litmus |
| LogP（分配係数） | 2.2log Kow = 2.20 @ pH 7.4 |
| LogS | -3.03 |
| 臭い | Very faint acrid odorNearly odorlessわずかな臭い |
| Color/Form | Bright yellow crystalsYELLOW NEEDLES FROM ALC, PETROLEUM ETHER |
| 溶解度 | 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.油：溶ける不溶性 |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| 融点 | 107105-107 °C105-107 °C(lit.) |
| 蒸気圧 | 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 |
| 沸点 | 262.49°C (rough estimate) |
| 密度 | 1.1153 (rough estimate) |
| 屈折率 | 1.5500 (estimate) |
| 貯蔵条件 | room temp |
| 外観・状態 | 結晶性 |
| 色 | 黄色 |
| 由来生物 | synthetic (organic) |
| Merck | 14,5831 |
| BRN | 1908453 |
| ヘンリー定数 | 3.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。光に敏感な場合があります。強力な酸化剤とは相容れない。 |
| 主な用途 | 医薬品（低分子化合物） |
| 化粧品成分の機能 | 香料 |
| 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（分配係数） | 2.200 |
| CAS データベース | 58-27-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Menadione(58-27-5) |
| EPAの化学物質情報 | Menadione (58-27-5) |
化学的特性
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.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| 有害性の概要 | 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 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products. Menadione is included on this list. |
用途
用途
ビタミンKの前駆体ではあるが、先進国ではサプリメントとしては用いられない。 低プロトロンビン血症の治療にも用いられる。
説明
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.
使用
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.
一般的な説明
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.
製法・合成法
製造方法
Menadione can be prepared by oxidizing 2-methylnaphthalene with chromic acid or hydrogen peroxide.
純化方法
Recrystallise it from 95% EtOH, or MeOH after filtration. It forms bright yellow crystals which are decomposed by light. Its solubility in EtOH is 1.7% and in *C6H6 it is 10%. It IRRITATES mucous membranes and skin. [Fieser J Biol Chem 133 391 1940, Beilstein 7 IV 2430.]