Menadiol diacetate
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)
Menadiol diacetate Usage And Synthesis
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
Menadiol diacetateSupplier
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Menadiol diacetate(573-20-6)Related Product Information
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- Methyl acrylate
- B12 VITAMIN B12
- 2-Methylnaphthalene
- Methyl eugenol
- Pancuronium bromide
- Methylparaben
- METHYL THIOPHENE-2-CARBOXYLATE
- Methyl acetate
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