Menadiol Explained

Menadiol is an organic compound with the formula C₆H₄(COH)₂(CH)(CH₃). It is formally a derivative of p-hydroquinone. The name vitamin K₄ can refer to:

• specifically this compound,^{[1] [2]}
• its various esters, e.g.
  • menadiol diacetate (acetomenaphthone),^{[3] [4]}
  • menadiol dibutyrate,^[4]
  • menadiol dimalonate, or^[2]
• its various salts, like
  • menadiol sodium diphosphate (Kappadione)^{[5] [2] [4]}
  • menadiol sodium disulfate.^[4]

Menadiol sodium diphosphate is approved in the UK for treatment and prevention of haemorrhage, mainly in obstructive jaundice (before and after surgery).^[6]

Menadiol is probably naturally produced by reduction of menadione ("vitamin K₃"; see) as an intermediate in the conversion from K₃ to MK-4.^[7] It can be oxidized in experimental conditions back to menadione.^[8]

Notes and References

1. Fiore LD. 2001. Anaphylactoid reactions to vitamin K. Journal of Thrombosis and Thrombolysis. 11. 2. 175–183. 0929-5305. 11406734. etal. 10.1023/A:1011237019082. 975055.
2. Book: The vitamins; chemistry, physiology, pathology, methods. Sebrell WH. Academic Press. 1971. 9780126337631. 2nd. 443. etal.
3. 2008. Vitamin K2 added for nutritional purposes in foods for particular nutritional uses, food supplements and foods intended for the general population and Vitamin K2 as a source of vitamin K added for nutritional purposes to foodstuffs, in the context of Regulation (EC) N° 258/97. EFSA Journal. 6. 11. 822. 10.2903/j.efsa.2008.822. 1831-4732. free.
4. Oketch-Rabah HA, Roe AL, Marles RJ. 2017. US Pharmacopeial Convention safety evaluation of menaquinone-7, a form of vitamin K. Nutrition Reviews. 75. 7. 553–578. 10.1093/nutrit/nux022. 28838081. 0029-6643.
5. Web site: Kappadione . go.drugbank.com.
6. Web site: Menadiol Diphosphate Tablets 10mg - Summary of Product Characteristics (SmPC) - (emc) . www.medicines.org.uk.
7. Shearer. Martin J.. Newman. Paul. March 2014. Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis. Journal of Lipid Research. 55. 3. 345–362. 10.1194/jlr.R045559 . free . 0022-2275. 3934721. 24489112.
8. Book: Fritz . Weber . August . Rüttimann . vanc . Vitamin K . Ullmann's Encyclopedia Of Industrial Chemistry . 2012 . Wiley-VCH . Weinheim . 10.1002/14356007.o27_o08 . 86263542 .