Menadione
Title: Menadione
CAS Registry Number: 58-27-5
CAS Name: 2-Methyl-1,4-naphthalenedione
Additional Names: 2-methyl-1,4-naphthoquinone; menaphthone; vitamin K2(0); vitamin K3
Trademarks: Kappaxin (Sterling Winthrop); Kayquinone (Abbott); Thyloquinone (BMS)
Molecular Formula: C11H8O2
Molecular Weight: 172.18
Percent Composition: C 76.73%, H 4.68%, O 18.58%
Literature References: Synthetic naphthoquinone derivative having physiologic properties of vitamin K, q.v. Prepn: Fieser, J. Biol. Chem. 133, 391 (1940). Toxicity study: Molitor, Robinson, Proc. Soc. Exp. Biol. Med. 43, 725 (1940). Alkylated in vivo to the bioactive metabolite, menaquinone-4, q.v.: C. Martius, H. O. Esser, Biochem. Z. 331, 1 (1958). Metabolism and tissue distribution: W. V. Taggart, J. T. Matschiner, Biochemistry 8, 1141 (1969). Improved synthesis: W. Adam et al., Angew. Chem. Int. Ed. 33, 2475 (1994).
Properties: Bright yellow crystals. Very faint acrid odor. mp 105-107°. Stable in air; dec by sunlight. Insol in water. One gram dissolves in about 60 ml alcohol, in 10 ml benzene, in 50 ml vegetable oils; moderately sol in chloroform, carbon tetrachloride. The alcoholic soln is neutral to litmus. Solutions may be heated to 120° without dec. Destroyed by alkalies and reducing agents. Keep protected from light. LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson).
Melting point: mp 105-107°
Toxicity data: LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson)
 
Derivative Type: Sodium bisulfite
CAS Registry Number: 130-37-0; 6147-37-1 (trihydrate)
CAS Name: 1,2,3,4-Tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonic acid sodium salt
Trademarks: Hykinone (Abbott); Klotogen (Abbott); K-Thrombin (Fawns & McAllan)
Molecular Formula: C11H9NaO5S
Molecular Weight: 276.24
Percent Composition: C 47.83%, H 3.28%, Na 8.32%, O 28.96%, S 11.61%
Literature References: Prepn: Moore, J. Am. Chem. Soc. 63, 2049 (1941). Structure: Carmack et al., ibid. 72, 844 (1950).
Properties: Occurs as the trihydrate. White, hygroscopic crystals. Discolors and may turn purple under the influence of light. One gram dissolves in ~2 ml water. Slightly sol in alcohol. Almost insol in ether, benzene.
 
Derivative Type: Dimethylpyrimidinol bisulfite
CAS Registry Number: 14451-99-1
Trademarks: Hetrazeen (Heterochemical)
Molecular Formula: C17H18N2O6S
Molecular Weight: 378.40
Percent Composition: C 53.96%, H 4.79%, N 7.40%, O 25.37%, S 8.47%
Literature References: Prepn: J. B. Nanninga et al., US 3328169 (1967 to Heterochemical). Efficacy in swine diets: R. W. Seerley et al., J. Anim. Sci. 42, 599 (1976).
Properties: Cryst powder, mp 215-217°. Soly in water ~1 g/100 ml. Slightly sol in alcohol. Insol in ether, benzene.
Melting point: mp 215-217°
 
Therap-Cat: Vitamin (prothrombogenic).
Therap-Cat-Vet: Vitamin (prothrombogenic); antidote to bishydroxycoumarin poisoning, including sweet clover poisoning.
Keywords: Vitamin/Vitamin Source; Vitamin K.

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