| Identification | More | [Name]
Menadiol diacetate | [CAS]
573-20-6 | [Synonyms]
1,4-DIACETOXY-2-METHYLNAPHTHALENE
2-methyl-1,4-naphthalenediol diacetate
2-METHYL-1,4-NAPHTHOHYDROQUINONE DIACETATE
ACETOMENAPHTHONE
MENADIOL DIACETATE
VITAMIN K4
VITAMIN K4 DIACETATE
1,4-Naphthalenediol,2-methyl-,diacetate
4-naphthalenediol,2-methyl-diacetate
Adaprin
Davitamon-K
Davitamon-K-oral
Kapilin
Kapilon
Kativpowder
Kayvite
Pafavit
Prokayvitoral
VitaminKdiacetate
VitavelK | [EINECS(EC#)]
209-352-1 | [Molecular Formula]
C15H14O4 | [MDL Number]
MFCD00021469 | [Molecular Weight]
258.27 | [MOL File]
573-20-6.mol |
| Chemical Properties | Back Directory | [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 | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 1 mg/ml | [Water Solubility ]
Insoluble in water | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319 | [Precautionary statements ]
P305+P351+P338 | [WGK Germany ]
WGK 3 | [RTECS ]
QJ5250000 | [HS Code ]
2936.29.5050 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Dam. 1 |
| Hazard Information | Back Directory | [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]
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 |
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