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Vitamin K4 (Acetomenaphthone)

Alias: Vitamin K4 (VK4); Acetomenaphthone; NSC 403062; NSC-403062; NSC403062
Cat No.:V5302 Purity: ≥98%
Vitamin K4 (also known as Acetomenaphthone),a synthetic hydrophilic menadione compound, is clinically used as hemostasis medicine.
Vitamin K4 (Acetomenaphthone)
Vitamin K4 (Acetomenaphthone) Chemical Structure CAS No.: 573-20-6
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Vitamin K4 (also known as Acetomenaphthone), a synthetic hydrophilic menadione compound, is clinically used as hemostasis medicine. Vitamin K4 also has anticancer activities by inducing tumor cytotoxicity in human prostate carcinoma PC-3 cells via the mitochondria-related apoptotic pathway. VK4 dose-dependently inhibited cell proliferation in PC-3 cells with an IC50 value of about 20.94 microM. Hoechst 33258 Staining results showed that VK4 caused DNA fragmentation in PC-3 cells. PI staining results indicated that VK4-induced PC-3 cell cycle arrest at the S phase. Further mechanistic studies revealed that VK4-mediated induction of apoptosis in PC-3 cell is associated with disruption of mitochondrial membrane potential, down-regulation of Bcl-2, and up-regulation of Bax, release of cytochrome c from mitochondria, and activation of caspase-3 and PARR Thus, VK4 might be useful in prostate cancer chemotherapy.
Vitamin K4 (CAS# 573-20-6), also known as Acetomenaphthone or Menadiol Diacetate, is a synthetic, chemically stabilized form of Vitamin K. It is a member of the naphthalenes class and is the diacetate form of the provitamin Vitamin K3 (menadione). With a molecular formula of C₁₅H₁₄O₄ and a molecular weight of 258.27, it plays an important role in the normal blood coagulation system.
Biological Activity I Assay Protocols (From Reference)
Targets
As a Vitamin K analog, Vitamin K4 targets the same pathway as other K vitamins. It serves as a precursor to menaquinone (Vitamin K2) in the body, which is an essential cofactor for the enzyme γ-glutamyl carboxylase. This enzyme is responsible for the post-translational carboxylation of glutamate residues on several proteins, including the coagulation factors II, VII, IX, X, and proteins C and S, which is critical for their biological activity.
ln Vitro
In vitro, Vitamin K4 has demonstrated anti-cancer functionality. Studies have shown that it induces apoptosis in prostate carcinoma cells. It inhibits the proliferation of PC3 prostate cancer cells with an IC₅₀ of 20.94 µM. At concentrations of 20 and 40 µM, it induces cell cycle arrest at the S phase and mitochondrial apoptosis in these cells.
ln Vivo
In vivo, as a Vitamin K analog, Vitamin K4 would be expected to support normal blood coagulation and bone metabolism. Its primary role is to ensure the proper functioning of the coagulation cascade. However, its specific effects in vivo are less well-characterized compared to other Vitamin K forms, as it is often used as a stable precursor.
Enzyme Assay
In vitro binding assays for Vitamin K4 are not standard, as it acts as a cofactor rather than a direct receptor ligand. However, its activity can be assessed in a functional assay measuring the γ-carboxylation of a peptide substrate by γ-glutamyl carboxylase. The enzyme is incubated with the substrate, Vitamin K4, and other cofactors, and the degree of carboxylation is measured to assess the compound's activity.
Cell Assay
In vitro cell-based assays for Vitamin K4 have been performed on cancer cell lines like PC3 prostate cancer cells. Cells are treated with varying concentrations of Vitamin K4 (e.g., up to 40 µM) for a defined period. Cell proliferation is then measured using assays like MTT, and apoptosis is assessed by measuring caspase activity or by flow cytometry after Annexin V/PI staining.
Animal Protocol
In vivo animal studies for Vitamin K4 would typically involve using a rat model of Vitamin K deficiency. Animals are fed a Vitamin K-deficient diet and then administered Vitamin K4 to assess its ability to restore normal blood coagulation, measured by the prothrombin time (PT). However, specific protocols are not detailed in the provided literature.
ADME/Pharmacokinetics
Specific pharmacokinetic data for Vitamin K4 are not extensively detailed in the provided literature. As a Vitamin K analog, it is likely to be absorbed from the gastrointestinal tract and transported to the liver, where it is converted to its active hydroquinone form. It is a synthetic compound intended for research use.
Toxicity/Toxicokinetics
As a synthetic Vitamin K, Vitamin K4 is generally well-tolerated at therapeutic doses. However, high doses of Vitamin K analogs can cause toxicity. The compound is not intended for human or veterinary use. Safety precautions should be followed when handling this compound.
References
Pharmazie. 2013 Jun;68(6):442-8.
Additional Infomation
Acetomenaphthone is a type of naphthalene compound.
Vitamin K4 is a synthetic and chemically stable form of Vitamin K. It is also known as Acetomenaphthone and Menadiol Diacetate. It is used as a research tool to study Vitamin K biology and as a potential anti-cancer agent. This product is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H14O4
Molecular Weight
258.2693
Exact Mass
258.089
CAS #
573-20-6
PubChem CID
11310
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
388.9±30.0 °C at 760 mmHg
Melting Point
113 °C
Flash Point
195.1±23.0 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.580
LogP
2.67
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
19
Complexity
352
Defined Atom Stereocenter Count
0
SMILES
O(C(C([H])([H])[H])=O)C1=C(C([H])([H])[H])C([H])=C(C2=C([H])C([H])=C([H])C([H])=C21)OC(C([H])([H])[H])=O
InChi Key
RYWSYCQQUDFMAU-UHFFFAOYSA-N
InChi Code
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
Chemical Name
1,4-Naphthalenediol, 2-methyl-, diacetate
Synonyms
Vitamin K4 (VK4); Acetomenaphthone; NSC 403062; NSC-403062; NSC403062
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~387.19 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.68 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (9.68 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (9.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.8719 mL 19.3596 mL 38.7192 mL
5 mM 0.7744 mL 3.8719 mL 7.7438 mL
10 mM 0.3872 mL 1.9360 mL 3.8719 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02309489 COMPLETEDWITH RESULTS Behavioral: Partner involvement Postpartum Period London School of Hygiene and Tropical Medicine 2015-01 Not Applicable
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