Menadiol
Title: Menadiol
CAS Registry Number: 481-85-6
CAS Name: 2-Methyl-1,4-naphthalenediol
Additional Names: 2-methyl-1,4-naphthohydroquinone; 2-methyl-1,4-naphthoquinol; dihydrovitamin K3
Molecular Formula: C11H10O2
Molecular Weight: 174.20
Percent Composition: C 75.84%, H 5.79%, O 18.37%
Literature 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).
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.
Melting point: mp 168-170° (MacCorquodale); mp 181° (Gaultier, Hauw)
 
Derivative Type: Diacetate
CAS Registry Number: 573-20-6
Additional Names: 1,4-Diacetoxy-2-methylnaphthalene; acetomenaphthone; vitamin K4
Trademarks: Kapilin (Glaxo); Prokayvit Oral (BDH); Vitavel K (Vitamins Ltd)
Molecular Formula: C15H14O4
Molecular Weight: 258.27
Percent Composition: C 69.76%, H 5.46%, O 24.78%
Literature 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.
Melting point: mp 112-114°
 
Derivative Type: Sodium diphosphate
CAS Registry Number: 131-13-5
CAS Name: 2-Methyl-1,4-naphthalenediol diphosphoric acid ester tetrasodium salt
Trademarks: Kappadione (Lilly); Synkavit (Roche); Synkayvite (Roche)
Molecular Formula: C11H8Na4O8P2
Molecular Weight: 422.08
Percent Composition: C 31.30%, H 1.91%, Na 21.79%, O 30.32%, P 14.68%
Literature 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.
 
Therap-Cat: Vitamin (prothrombogenic).
Keywords: Vitamin/Vitamin Source; Vitamin K.

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