5831. Menadione

Nomenclature

CAS number: 58-27-5
2-Methyl-1,4-naphthalenedione; 2-methyl-1,4-naphthoquinone; menaphthone; vitamin K2(0); vitamin K3; Kappaxin (Sterling Winthrop); Kayquinone (Abbott); Thyloquinone (BMS).
C11H8O2; mol wt 172.18.
C 76.73%, H 4.68%, O 18.58%.

Description and 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).

Chemical structure

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).

Derivative

Sodium bisulfite.

Nomenclature

CAS number: 130-37-0; 6147-37-1 (trihydrate)
1,2,3,4-Tetrahydro-2-methyl-1,4-dioxo-2-naphthalenesulfonic acid sodium salt; Hykinone (Abbott); Klotogen (Abbott); K-Thrombin (Fawns & McAllan).
C11H9NaO5S; mol wt 276.24.
C 47.83%, H 3.28%, Na 8.32%, O 28.96%, S 11.61%.

Description and 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

Dimethylpyrimidinol bisulfite.

Nomenclature

CAS number: 14451-99-1
Hetrazeen (Heterochemical).
C17H18N2O6S; mol wt 378.40.
C 53.96%, H 4.79%, N 7.40%, O 25.37%, S 8.47%.

Description and 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.

Therapeutic Category

Vitamin (prothrombogenic).

Therapeutic Category (Veterinary)

Vitamin (prothrombogenic); antidote to bishydroxycoumarin poisoning, including sweet clover poisoning.

Keywords

Vitamin/Vitamin Source; Vitamin K