Menadiol diacetate CAS 573-20-6
Menadiol diacetate Basic information
| Product Name: | Menadiol diacetate |
| Synonyms: | 1,4-Naphthalenediol,2-methyl-,diacetate;Kayvite;Pafavit;Prokayvitoral;VitaminKdiacetate;VitavelK;ACETOMENAPHTHONE;MENADIOL DIACETATE |
| CAS: | 573-20-6 |
| MF: | C15H14O4 |
| MW: | 258.27 |
| EINECS: | 209-352-1 |
| Product Categories: | Vitamins and derivatives;Inhibitors;Biochemistry;Vitamins |
| Mol File: | 573-20-6.mol |
Menadiol diacetate Chemical Properties
| Melting point | 113 °C |
| Boiling point | 361.52°C (rough estimate) |
| density | 1.2105 (rough estimate) |
| refractive index | 1.4872 (estimate) |
| storage temp. | Sealed in dry,Room Temperature |
| Water Solubility | Insoluble in water |
| solubility | DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 1 mg/ml |
| form | powder to crystal |
| color | White to Almost white |
| InChI | InChI=1S/C15H14O4/c1-9-8-14(18-10(2)16)12-6-4-5-7-13(12)15(9)19-11(3)17/h4-8H,1-3H3 |
| InChIKey | RYWSYCQQUDFMAU-UHFFFAOYSA-N |
| SMILES | C1(OC(=O)C)=C2C(C=CC=C2)=C(OC(=O)C)C=C1C |
| CAS DataBase Reference | 573-20-6(CAS DataBase Reference) |
Safety Information
| WGK Germany | WGK 3 |
| RTECS | QJ5250000 |
| HS Code | 2936.29.5050 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Dam. 1 |
| Uses | Vitamin K4, is a chemically synthesized Vitamin K which plays an important role in the normal blood coagulation system. |
| Definition | ChEBI: Acetomenaphthone is a member of naphthalenes. |
| Biological Activity | Vitamin K4 elicits anti-cancer functionality and induces apoptosis in prostate carcinoma. |
| Synthesis | 58-27-5 108-24-7 573-20-6 General procedure for the synthesis of vitamin K4 from 2-methyl-1,4-naphthoquinone (20.0 g) and acetic anhydride (29.65 g): 2-methyl-1,4-naphthoquinone was first dissolved in ethyl acetate (200 g). Subsequently, acetic anhydride, 4-dimethylaminopyridine (DMAP, 1.42 g), and palladium/carbon catalyst (Pd/C, 0.6 g) were added to the solution. The reaction mixture was stirred at room temperature in a hydrogen atmosphere overnight. Upon completion of the reaction, the Pd/C catalyst was removed by filtration. The filtrate was washed with brine and the organic layer was separated. The organic layer was concentrated and recrystallized in a solvent mixture of water (60 g) and isopropanol (IPA, 80 g) to yield 28.0 g of vitamin K4 as white crystals (yield: 84.2%, HPLC purity: 99.8%). The structure of the compound was characterized by 1H-NMR with the following chemical shifts: δ 2.27 (s, 3H), 2.46 (s, 3H), 2.50 (s, 3H), 7.27 (s, 1H), 7.55-7.62 (m, 2H), 7.85-7.89 (d, 2H). |
| References | [1] Patent: WO2016/60670, 2016, A1. Location in patent: Paragraph 0036-0041 [2] Patent: TW2016/15603, 2016, A. Location in patent: Paragraph 0049-0051 [3] Journal of Crystallographic and Spectroscopic Research, 1989, vol. 19, # 2, p. 307 - 316 [4] Archiv der Pharmazie, 1973, vol. 306, # 4, p. 257 - 267 |
Menadiol diacetate Preparation Products And Raw materials
| Raw materials | Sodium acetate-->2-Methylnaphthalene-->Methylnaphthalene-->Menadione-->Acetic anhydride-->Palladium-->Hydrogen-->Ethyl acetate-->4-Dimethylaminopyridine |
