Menadione sodium bisulfite Chemical Properties

Melting point:

121-124°C

storage temp. 

-20°C

solubility 

H2O: ≥50mg/mL, clear, colorless to faintly yellow

form 

Solid

color 

White to off-white

InChI

InChI=1S/C11H10O5S.Na.H/c1-11(17(14,15)16)6-9(12)7-4-2-3-5-8(7)10(11)13;;/h2-5H,6H2,1H3,(H,14,15,16);;

InChIKey

JWNUEPMMANLFQO-UHFFFAOYSA-N

SMILES

O=C1C(CC(=O)C2=CC=CC=C12)(C)S(O)(=O)=O.[NaH]

EPA Substance Registry System

Menadione sodium bisulfite (130-37-0)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36-50/53-36/38

Safety Statements 

26-61-60-24/25

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

Menadione sodium bisulfite Usage And Synthesis

Detection method

Menadione sodium bisulfite was detected under the following separation conditions: uncoated fused silica capillary (55 cm × 75 μnm), background electrolyte 40 mmol/L phosphate + 50 mmol/L sodium dodecylsulfate (SDS) (pH 7.5), operation voltage 15 kV and UV detection wavelength 231 nm. The experimental results show that menadione sodium bisulfite in injection was quantified with pyridoxal 5-phosphate as the internal standard, which means that the determination of menadione sodium bisulfite was very simple, feasible and satisfactory.

Description

Menadione sodium bisulfite (MSB, also known as vitamin K3), is a crucial growth regulator mediating plant defense response. This substance is used clinically in China to treat hemorrhagic diseases caused by vitamin K deficiency and globally as a vitamin K supplement. This compound and its complex (MSBC) are water-soluble compounds. Menadione and the menadione sodium bisulfite complex are the sources of vitamin K activity in commercial laboratory rodent diets. Menadione possesses high biological activity, but its absorption depends on the amount of fat in the diet. Compared with Menadione, the menadione sodium bisulfite complex is more readily absorbed and is almost as active on a molar basis as phylloquinone. XTT, a tetrazolium salt, could converted to formazan in the presence of an electron coupling reagent such as menadione sodium bisulfite. The formed formazan does not need to be solubilized. Hence, the XTT test, a cytotoxicity evaluation method, is quicker and safer compared with MTT[1-2].

Chemical Properties

white powder

Originator

Kavitol,Lannacher Heilmittel

Uses

Menadione sodium bisulfite has been used:

• as a priming agent in tomato for improving salt tolerance
• to induce reactive oxygen species (ROS) in human lung epithelium BEAS-2B microtissues
• to induce endogenous superoxide production in mouse C17.2 neural stem cells

Definition

ChEBI: An organic sodium salt that is the monosodium salt of menadione sulfonate. A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation i vivo.

Manufacturing Process

The 2-naphthalenesulfonic acid, 1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-, sodium salt, trihydrate can be prepared by mixing the 2-methyl-1,4- naphthoquinone with the bisulphite salt in the presence of water. Ordinarily gentle warming of the aqueous mixture is preferred to facilitate solution. The mixture of 2-methyl-1,4-naphthoquinone (250 mg; 1 molar equivalent); sodium bisulphite (149 mg; 1 molar equivalent); distilled water (250 ml) or 2- methyl-1,4-naphthoquinone (250 mg; 1 molar equivalent); potassium bisulphate (349 mg; 2 molar equivalent); distilled water 250 ml may be used. These examples representing preferred ratios of ingredients are merely illustrative and are not to be interpreted as limiting.
The bisulphite addition compounds have been found to be stable in sunlight and also to be heat stable. Tests, for example, carried out in ampoules have shown aqueous solutions of the compounds not to be decomposed after exposure to a month's sunlight, while other tests have shown the solutions of such compounds to retain their original potency (a) when stored in an oven at 60°C for 15 days or (b) when sterilized at 15 pounds for 0.5 hour in an autoclave at about 122°C. These properties emphasize the radical differences between the stable salts and the properties of 2-methyl-1,4-naphthoquinone, the characteristic instability of which is illustrated by its sensitivity, i. e., decomposition, when exposed to light.
The bisulphite addition compounds have a vitamin K activity equal to that of the 2-methyl-1,4-naphthoquinone contained in the molecule. The compounds, although suitable for oral administration, are particularly adaptable in aqueous solution for parenteral administration in the treatment of hemorrhagic conditions.

brand name

Hykinone (Abbott); Klotogen (Abbott).

Therapeutic Function

Prothrombogenic vitamin

Biochem/physiol Actions

Menadione sodium bisulfite is a water-soluble form of menadione, which belongs to the Vitamin K class of compounds. These are necessary for the biosynthesis of prothrombin and other blood clotting factors. Menadione is a prothrombogenic compound and is used as a model quinone in cell culture and in vivo investigations. Menadione has been shown to affect gap-junctional intercellular communication by mediation of tyrosine phosphorylation. Menadione has demonstrated cytotoxic activity against a variety of cell lines and can induce apoptosis in cultured cells, such as osteoclasts and osteoblasts, via elevation of peroxide and superoxide radical levels.An HPLC method for detection of menadione sodium bisulfite in multivitamin formulations has been published. A chemiluminescence assay for menadione sodium bisulfite in pharmaceutical preparations and biological fluids has been reported.

Contact allergens

1

Side effects

Inflammation of the walls of a vein
Facial flushing
Cardiovascular collapse
Severe shock-like reactions
Sweating Injection site reactions
Chest constriction
Pain
Shortness of breath
Bluish discoloration of the skin

References

[1] Zhang Y, et al. Menadione sodium bisulfite inhibits the toxic aggregation of amyloid-β(1-42). Biochimica et Biophysica Acta (BBA) - General Subjects, 2018; 1862: 2226-2235.
[2] Lustgarten M, et al. An Objective Appraisal of the Free Radical Theory of Aging. Handbook of the Biology of Aging, 2011; 177-202.

Menadione sodium bisulfite(130-37-0)Related Product Information

• Sodium chloride
• B12 VITAMIN B12
• Sodium bisulfite
• Sodium bicarbonate
• Sodium hydroxide
• Sodium acetate
• Sodium benzoate
• Sodium metabisulfite
• Hydrogen Sulfide
• Hydrogen
• Diclofenac sodium
• Ammonium bisulfite
• Tocopheryl acetate
• DL-METHIONINE METHYLSULFONIUM CHLORIDE
• D-Biotin
• Vitamin K1
• Ascorbyl Palmitate
• Vitamin D3