5830. Menadiol

Nomenclature

CAS number: 481-85-6
2-Methyl-1,4-naphthalenediol; 2-methyl-1,4-naphthohydroquinone; 2-methyl-1,4-naphthoquinol; dihydrovitamin K3.
C11H10O2; mol wt 174.20.
C 75.84%, H 5.79%, O 18.37%.

Description and references

Synthetic naphthoquinol derivative having physiological properties of Vitamin K, q.v.; starting material for prepn of menaquinones, q.v. Prepn: K. Fries, W. Lohmann, Ber. 54, 2912 (1921); D. W. MacCorquodale et al., J. Biol. Chem. 131, 357 (1939); C. D. Snyder, H. Rapoport, J. Am. Chem. Soc. 96, 8046 (1974). Crystal structure: J. Gaultier, C. Hauw, Acta Crystallogr. 25B, 51 (1969). Bioactivity and tissue distribution: M. J. Thierry, J. W. Suttie, J. Nutr. 97, 512 (1969).

Chemical structure

Properties

White needles from dil alc, mp 168-170° (MacCorquodale); also reported as mp 181° (Gaultier, Hauw). Slightly sol in benzene, chloroform; easily sol in acetone, alcohol.

Derivative

Diacetate.

Nomenclature

CAS number: 573-20-6
1,4-Diacetoxy-2-methylnaphthalene; acetomenaphthone; vitamin K4; Kapilin (Glaxo); Prokayvit Oral (BDH); Vitavel K (Vitamins Ltd).
C15H14O4; mol wt 258.27.
C 69.76%, H 5.46%, O 24.78%.

Description and references

Prepn: Sah et al., Ber. 73, 762 (1940); Rec. Trav. Chim. 59, 461 (1940).

Properties

Crystals, mp 112-114°. Practically insol in water. Slightly sol in cold alc; sol in 3.3 parts boiling alc, in acetic acid.

Derivative

Sodium diphosphate.

Nomenclature

CAS number: 131-13-5
2-Methyl-1,4-naphthalenediol diphosphoric acid ester tetrasodium salt; Kappadione (Lilly); Synkavit (Roche); Synkayvite (Roche).
C11H8Na4O8P2; mol wt 422.08.
C 31.30%, H 1.91%, Na 21.79%, O 30.32%, P 14.68%.

Description and references

Prepn: Fieser, Fry, J. Am. Chem. Soc. 62, 228 (1940).

Properties

Prepd as the hexahydrate, white to pinkish powder. Salty taste. Very sol in water. Practically insol in methanol, ethanol, ether, acetone.

Therapeutic Category

Vitamin (prothrombogenic).

Keywords

Vitamin/Vitamin Source; Vitamin K