Menadione sodium bisulfite

R,5)-vitamin (cis, trans-mixture), menadione sodium bisulfite, menadione dimethylpyrimidinol bisulfite... 

In addition to its industrial importance as an intermediate in the synthesis of vitamin K, menadione, or more specifically, salts of its bisulfite adduct, are important commodities in the feed industry and are used as stabilized forms in this appHcation. Commercially significant forms are menadione dimethyl pyrimidinol (MPB) (10) and menadione sodium bisulfite (MSB) (11). MSB is sold primarily as its sodium bisulfite complex. The influence of feed processing, ie, pelleting, on the stabiUty of these forms has been investigated (68). The biological availabiUties and stabiUty of these commercial sources has been deterrnined (69,70). 

Another quinone-related natural compound evaluated by Schrader etal is SeaKleen , a commercial biocide used to treat the ballast water of ships to help prevent the spread of pest organisms such as algae. SeaKleen consists of menadione sodium bisulfite, a water-soluble form of menadione... 

Asker AF, Habib MJ. Photostabilization of menadione sodium bisulfite by glutathione. J Parenter Sci Technol 1989 43 204—207. 

Common Name Menachinonum natrium bisulfurosum Menadione sodium bisulfite Menadionnatriumbisulfit Menaphthone sodium bisulphite ... 

PhyUoquinone is vitamin Ki, menaquinones are vitamin K2, and the synthetic compounds menadione and menadiol are vitamin K3. In addition to menadione itself, menadiol diacetate (acetomenaphthone) is used in pharmaceutical preparations, and two water-soluble derivatives, menadione sodium bisulfite and menadiol sodium phosphate, have been used for administration of the vitamin by injection and in patients with malabsorption syndromes that would impair the absorption of menadione, phylloquinone, and menaquinones, which are lipid soluble. 

Drugs whose decomposition rates are influenced by the pH include doxorubicin hydrochloride (47), minoxidil (48), menadione sodium bisulfite (67), metronidazole (68), riboflavin (69), colchicine (70), tetracycline hydrochloride (71), phenobarbital (72), dacarbazine (73), furosemide (74), daunorubicin hydrochloride (75), and demeclo-cycline hydrochloride (76). Figures 3 to 6 illustrate how the pH of the solution can influence the degradation rate of some of the reported photolabile drugs. 

S. M. Billedeau, Fluorimetric determination of vitamin K3 (menadione sodium bisulfite) in synthetic animal feed by high-performance liquid chromatography using a post-column zinc reducer,... 

A. J. Speek, J. Schrijver and W. Schreurs, Fluorimetric determination of menadione sodium bisulfite (vitamin K3) in animal feed and premixes by high-performance liquid chromatography with post-column derivatization, / Chromatogr., 301,441,1984. 

T. Ruzgas, Amperometric monitoring of redox activity in living yeast cells Comparison of menadione and menadione sodium bisulfite as electron transfer mediatOTS, Electrochemical Communications, 6(2), 219-224 (2004). 

Hetrogai iL [Heterochem] Menadione sodium bisulfite complex. 

Trihydrate, white hygroscopic, crystals. Discolors and may turn purple under the Influence of light. One gram dissolves in about 2 ml water. Slightly sol in alcohol almost insol in ether benzene, Addition of NaOH soln to a soln of menadione sodium bisulfite produces a bright yellow precipitate. of menadione. 

Menadione sodium bisulfite (vitamin K3) Romaguera et al. 1980 Camarasa and Barnadas 1982 Dinis et al. 1988... 

Figure 1 Structural formulas of some K vitamers (1) vitamin Ki(20), (VKl), phylloquinone or 2-methyl-3-eicosa-2 -ene-l,4-naphthoquinone (2) trideuterium labeled VKl, VKl-rfj, 2-methyl-rf3-3-eicosa-2 -ene-1,4-naphthoquinone as internal standard for GC-MS analysis (3) VKl-epoxide (4) menaquinone-4, MK4, 2-methyl-3-tetraprenyl-l,4-naph-thoquinone, as an example of the MKn series (5) VKl-heptafluorobutyryl ester after reductive acylation of VKl (6) menadione, vitamin K3 (VK3), or 2-methyl-1,4-naphthoqui-none (7) menadione sodium bisulfite (MSB), water-soluble form of VK3.

Menadione, or vitamin K3 (VK3), is the synonym for 2-methyl-l,4-naphthoquinone, and does not occur in nature. It has to be synthesized, and acts as an intermediate in synthesis of K vitamins. VK3, as a provitamin, can be transformed to MK4 by micro-organisms. Menadione has been shown to exhibit antitumor activity in rodent and human tumor cells (6-9). A water-soluble form of the provitamin VK3 (menadione sodium bisulfite, MSB see Structures 6 and 7 in Fig. 1) is often added to animal feed, and after treatment with aqueous Na2C03 (destroying the bisulfite salt) and/or irradiation with UV-radiation (10), it can be chromatographed and analyzed in usual ways. 

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