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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.
Formula: C₁₁H₉NaO₅S (often hydrated, e.g., C₁₁H₉NaO₅S·3H₂O)
CAS: 130-37-0
Key Feature: The sulfonate group (-SO₃Na) confers high water solubility.
Function: Acts as a pro-vitamin, converting in vivo to active vitamin K (menadione, then menaquinone-4).
Primary Use: Widely added to animal feeds (poultry, swine) and used in veterinary medicine to prevent and treat vitamin K deficiency-related bleeding disorders. Its use in human supplements is limited due to potential toxicity concerns at high doses.
Menadione sodium bisulfite (MSB) is a water-soluble synthetic vitamin K analog with the chemical formula C₁₁H₉NaO₅S. Its key chemical characteristics are:
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).
CAS Number: 130-37-0.
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.
Primary Use: It serves as a water-soluble source of vitamin K activity, primarily used in animal feed (poultry, swine) and veterinary medicine to prevent vitamin K deficiency bleeding disorders (hemorrhagic diathesis). It is not typically used as a direct human dietary supplement due to safety concerns regarding high doses of synthetic vitamin K₃.
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