Menadiol diacetate

Figure 45-7. The vitamin K vitamers. Menadiol (or menadione) and menadiol diacetate are synthetic compounds that are converted to menaquinone in the liver and have vitamin Kactivity.

Figure 5.1. Vitamin K vitamers and the vitamin K antagonists dicoumarol and war-farin. Relative molecular masses (Mr) phyUoquinone, 450.7 menaquinone-4, 447.4 menaquinone-5, 512.8 menaquinone-6, 580.0 menaquinone-7, 649.0 menaquinone-8,717.1 menadione, 172.2 menadiol diacetate, 258.3 dicoumarol, 336.3 and warfarin 308.3.

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. 

Carbon-14-labeled menadiol diacetate in small physiological doses is converted in vivo to vitamin K2i2oit and the side chain probably originates from mevalonic acid. This suggc.sts that iiKnadiunc may be an intermediate or a provitamin K. "... 

After administration of C Mabeled menadiol diacetate to vitamin K-... 

As mentioned in Section VI, Martius (1956) has shown that menadione is transformed in the animal body into a vitamin K2 compound with 20 C-atoms in the isoprene side chain. This was proved by the administration of C -labeled menadiol diacetate to vitamin K-deficient chicks. In agreement with the results of Green et al, (1956) on the vitamin K content of mitochondria, most of the activity was found in the mitochondria fraction of heart, liver, and kidney, the highest being in that of heart. 

Vitamin K3 (menadione, MK-0,2-methyl-1,4-naphthoquinone) is a synthetic substance. The product of menadione reduction, known as menadiol (2-methylnaphthalene-l,4-diol), and derived compounds, such as the fat-soluble menadiol diacetate or menadiol dibutyrate and the water-soluble sodium salt of menadiol diphosphate, are referred to as vitamin K4. Activity of vitamin K was also detected in the synthetic monoamino analogues and diamino analogues of menadiol, for example, in l-amino-4-hydroxy-3-methylnaphthalene (vitamin K5), l,4-diamino-2-methylnaphthalene (vitamin Kg) and l-amino-4-hydroxy-2-methylnaphthalene (vitamin K ). 

Methyl-1,4-naphthalenediol diacetate Menadiol diacetate C15H14O4 573-20-6 258.270 pr (al) 113 vs EtOH... 

Lauryl bromide 1190 Menadiol diacetate 7474 2-Methoxycarbonylethyl methyl ... 

Vitamin (menadiol diacetate, MDD) is a significant candidate as a synthetic substitute for natural vitamins K although its biological activity is two to three times lower, it is more stable and easiest to store [108],... 

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