130-37-0

Basic information

• Product Name: Menadione sodium bisulfite
• Synonyms: 1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonicacidsodiumsalt;1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonicacisodiumsalt;2,3-dihydro-2-methyl-1,4-naphthoquinone-2-sulfonatesodium;2-methyl-1,4-naphthoquinonesodiumhydrogensulfite;2-methylnaphthoquinonesodiumhydrogensulfite;2-Naphthalenesulfonicacid,1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-,sodiumsalt;golagenk;hemoklot
• CAS NO: 130-37-0
• Molecular Formula: C11H9NaO5S
• Molecular Weight: 276.24
• EINECS: 204-987-0
• Product Categories: Pharmaceutical intermediates
• Mol File: 130-37-0.mol

Chemical Properties

• Melting Point: 121-124°C
• Appearance: Crystalline powder
• Storage Temp.: −20°C
• Solubility: H2O: ≥50mg/mL, clear, colorless to faintly yellow
• CAS DataBase Reference: Menadione sodium bisulfite(CAS DataBase Reference)
• NIST Chemistry Reference: Menadione sodium bisulfite(130-37-0)
• EPA Substance Registry System: Menadione sodium bisulfite(130-37-0)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36-50/53-36/38
• Safety Statements: 26-61-60-24/25
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 130-37-0(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Originator

Kavitol,Lannacher Heilmittel

Uses

Menadione sodium bisulfite has been used:as a priming agent in tomato for improving salt toleranceto induce reactive oxygen species (ROS) in human lung epithelium BEAS-2B microtissuesto 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.

InChI:InChI=1/C11H10O5S.Na/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);/q;+1/p-1

Synthetic route

menadione (58-27-5) → Hykinone (130-37-0)

Conditions	Yield
With sodium hydrogensulfite In ethanol; water at 75℃; Temperature;	78%
With sodium hydrogensulfite In chloroform; water at 20 - 40℃; for 2h;

2-Methylnaphthalene (91-57-6) → Hykinone (130-37-0)

Conditions	Yield
With sodium hydrogen sulfite In water; toluene at 25℃; for 2h; Product distribution / selectivity;	17.1%

Hykinone (130-37-0) → menadione (58-27-5)

Conditions	Yield
With sodium hydroxide In chloroform; water at 20℃; Product distribution / selectivity;	100%
With water; sodium carbonate at 25℃; for 120h; Time;

Hykinone (130-37-0) + thiourea (17356-08-0) → 5-Hydroxy-4-methyl-naphth<2,1-d>1,3-oxathiol-2-on (74677-72-8)

Conditions	Yield
With hydrogenchloride In acetic acid for 1h; Cyclization; Heating;	93%

Hykinone (130-37-0) + aqueous NaOH-solution → menadione (58-27-5)

water (7732-18-5) + semicarbazide hydrochloride (563-41-7) + sodium acetate (127-09-3) + Hykinone (130-37-0) → sodium-salt of/the/ 1-oxo-4-semicarbazono-2-methyl-1.2.3.4-tetrahydro-naphthalene-sulfonic acid-(2)

Conditions	Yield
analoge Reaktionen mit Phenylhydrazin und mit 4-Nitro-phenylhydrazin;

piperazine (110-85-0) + Hykinone (130-37-0) → bis(1,2,3,4-tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonate)hexahydropyrazine

Conditions	Yield
With hydrogenchloride In water at 20℃; for 1.5h;

Upstream product

• 58-27-5 menadione 
• 91-57-6 2-Methylnaphthalene 
• 71-43-2 benzene 
• 1590-08-5 2-methyl-1-tetralone 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 90-15-3 α-naphthol 

Downstream Products

• 58-27-5 menadione 

Related news

Detection of Menadione sodium bisulfite (cas 130-37-0) (vitamin K 3 ) by reversed-phase high performance liquid chromatography with series dual-electrode amperometric detector09/29/2019

A reversed-phase high-performance liquid chromatography with series dual glassy carbon electrodes for the amperometric detection of water-soluble menadione is described. The complex post-column derivatization reaction and the high background currents were avoided. The menadione sodium bisulfit...detailed

Chemiluminescence analysis of Menadione sodium bisulfite (cas 130-37-0) and analgin in pharmaceutical preparations and biological fluids09/28/2019

A novel chemiluminescence (CL) flow system for two sulfite-containing drugs, namely, menadione sodium bisulfite (MSB) and analgin is described. It is based on the weak chemiluminescence induced by the oxidation of sulfite group in drugs with dissolved oxygen in the presence of acidic Rh6G. Tween...detailed

Study on the electrochemiluminescent behavior of Menadione sodium bisulfite (cas 130-37-0) in presence of luminol10/01/2019

Menadione sodium bisulfite (MSB) is a stable water-soluble derivative of Vitamin K 3 , which is found to be able to enhance the ECL of luminol at potential of 0.88V in phosphate buffer solution. The conditions for the enhanced ECL, such as the selection of the type of buffer solution, ap...detailed

Study on sensitized photochemical fluorescence of Menadione sodium bisulfite (cas 130-37-0) and its application in pharmaceutics analysis09/27/2019

Menadione sodium bisulfite (MSB), vitamin K 3 , a non-fluorescent compound, was converted into an intensive fluorescent compound (λ e x /λ e m =340 nm/465 nm) on irradiation with ultraviolet radiation in an anaerobic alkaline medium, and acetone showed a strong ...detailed

Amperometric monitoring of redox activity in living yeast cells: comparison of menadione and Menadione sodium bisulfite (cas 130-37-0) as electron transfer mediators09/25/2019

An amperometric method was applied for real-time monitoring of intracellular redox enzyme activity. Baker's yeast (Saccharomyces cerevisiae) cells were immobilized on platinum microband electrodes and mediated anodic currents were measured. The currents were observed in the absence and in the pr...detailed

Relevant articles and documents

New route to vicasol, a water-soluble form of vitamin K3

A procedure was suggested for preparing vicasol in an approximately 85% yield in a two-phase system consisting of concentrated (5 6 M) aqueous solution of NaHSO3 and a solution of 2-methyl-1,4-naphthoquinone in an incombustible organic solvent

Preparation method of menadione sodium hydrogen sulfite

The invention provides a preparation method of menadione sodium hydrogen sulfite. The preparation method comprises the following steps of: by taking alpha-methyl-gamma-butyrolactone and benzene as raw materials, preparing 2-methyl-3, 4-dihydro-1 (2H)-naphthalenone through Friedel-Crafts reaction; carrying out halogenation reaction on the 2-methyl-3, 4-dihydro-1 (2H)-naphthalenone and a halogenation reagent at the ortho position of carbonyl, and carrying out alkali elimination to prepare 2-methyl-1-naphthol; oxidizing the 2-methyl-1-naphthol through air to obtain 2-methyl-1, 4-naphthoquinone; and carrying out addition reaction on the 2-methyl-1, 4-naphthoquinone and sodium hydrogen sulfite to prepare the menadione sodium hydrogen sulfite. According to the method, the raw materials are cheap, easily available and low in cost; the process operation is safe, simple and convenient, less process wastewater is generated, and the method is green and environment-friendly; and the stability of the raw materials and intermediate products is high, high reaction activity and selectivity are high, reaction conditions are easy to realize, side reactions are few, the purity and yield of the product are high, and industrial production of the menadione sodium bisulfite can be facilitated.

Green preparation method of menadione sodium bisulfite

The invention provides a preparation method of menadione sodium bisulfite. The method comprises the following steps of: by using cheap and easily available 3, 4-dihydro-1 (2H)-naphthalenone as a raw material, carrying out halogenation-elimination to obtain 1-naphthol; carrying out methylation reaction to generate 2-methyl-1-naphthol; carrying out air oxidation on the 2-methyl-1-naphthol to obtain 2-methyl-1, 4-naphthoquinone; and carrying out addition reaction on the 2-methyl-1, 4-naphthoquinone and sodium hydrogen sulfite so as to obtain the menadione sodium bisulfite. The method has the advantages of cheap and easily available raw materials, low cost, safe, simple and convenient process operation, less process wastewater generation, green and environment-friendly performance, high stability of raw materials and intermediate products, high reaction activity and selectivity, easy realization of reaction conditions, few side reactions and high product purity and yield, and can facilitate the industrial production of the menadione sodium bisulfite.

A method for continuous preparation of menadione sodium bisulfite (by machine translation)

The invention discloses a tubular method for continuous preparation of menadione sodium bisulfite, the method comprises the steps of: preheating to 50-80 °C β-menadione of the solution with the sodium metabisulfite solution through the metering pump, respectively, is mixed by the mixer, the mixed material from entering into the tubular reactor for reaction, control reaction solution temperature is 50-80°C, in the tubular reactor the reaction residence time in 1-15min; a reactor outlet the cooling crystallization materials, centrifugal separation of the solid product, washing, drying by menadione sodium bisulfite. This invention adopts the tubular reactor to produce the menadione sodium bisulfite, production cycle is shortened, the product yield is high, stable quality; easy control of reaction conditions, the operation is simple and safe, easy automation control; the continuous production can be realized, the industry requires only a small amount of investment in large-scale production can be realized. (by machine translation)

Method for producing 2-methyl-1,4-naphthoquinone

[PROBLEM TO BE SOLVED]: To provide a method for easily collecting high pure 2-methyl-1,4-naphthoquinone in the shape to converts easily to hydrosulfite in a high yield from hydrogen peroxide oxidation reaction mixture of 2-methylnaphthalene in aliphatic carboxylic acid. [SOLUTION]: The method for collecting 2-methyl-1,4-naphthoquinone into aromatic hydrocarbon layer characterized by concentrating the oxidation reaction mixture obtained by liquid phase oxidizing 2-methylnaohthalene in aliphatic carboxylic acid so that the density of the reaction product may become 30-80 wt% by distillation, and by touching with aromatic hydrocarbon solvent and water for the layer separation.