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Menadione sodium bisulfite (MSB) is a water-soluble synthetic form of vitamin K₃ (menadione). Chemically, it is the addition compound formed when sodium bisulfite (NaHSO₃) reacts with menadione (2-methyl-1,4-naphthoquinone) at the quinone's 3-position. It is widely used in animal feed and veterinary medicine to prevent vitamin K deficiency-related bleeding disorders.
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Product Name | Menadione Sodium Bisulfite |
CAS NO. | 6147-37-1 |
Formula | C₁₁H₉NaO₅S·3H₂O |
Feature | High water solubility due to the sulfonate group (-SO₃Na) |
Function | Acts as a pro-vitamin, converting in vivo to active vitamin K (menadione, then menaquinone-4). |
Brand | Fortunachem |
Menadione sodium bisulfite (MSB) is a water-soluble synthetic vitamin K analog with the chemical formula C₁₁H₉NaO₅S.
Chemical Characteristics
Core Structure: Derived from menadione (vitamin K₃, 2-methyl-1,4-naphthoquinone).
Chemical Modification: Formed by the nucleophilic addition of sodium bisulfite (NaHSO₃) across one of the carbonyl groups (C=O) of the quinone ring. This creates a sulfonate adduct (-C(OH)-SO₃Na).
Structure: Typically represented as the addition product at the 3-position: 2-methyl-1,4-naphthoquinone-3-sodium sulfonate or 3-(sodiosulfonyl)-2-methyl-1,4-naphthoquinone. The active form often exists as a hydrate (e.g., C₁₁H₉NaO₅S·3H₂O).
Key Properties
Water Solubility: The sulfonate group makes it highly water-soluble, unlike the lipid-soluble menadione.
Pro-Vitamin: It readily dissociates/reconverts to biologically active menadione in vivo.
Stability: More stable in aqueous solutions than menadione itself.
Menadione sodium bisulfite is primarily used as a water-soluble source of vitamin K activity in animal nutrition. It is widely added to the feed of poultry and swine to prevent and treat vitamin K deficiency-related bleeding disorders, such as hemorrhagic diathesis. It is also used in veterinary medicine for the same purpose. However, due to potential toxicity concerns associated with high doses of synthetic vitamin K₃, its use in human dietary supplements is limited.
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