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.

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)

Biological Activity

References	Pharmazie. 2013 Jun;68(6):442-8.
Additional Infomation	Acetomenaphthone is a member of naphthalenes.

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. 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.