Menadiol

Menadiol is an organic compound with the formula C₆H₄(COH)₂(CH)(CH₃). It is formally the p-hydroquinone derivative of 2-methylnaphthalene. 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]

Quick facts Names, Identifiers ...

Menadiol

Names
Preferred IUPAC name 2-Methylnaphthalene-1,4-diol
Other names 2-Methyl-1,4-naphthalenediol; 2-Methyl-1,4-dihydroxynaphthalene
Identifiers
CAS Number	481-85-6
3D model (JSmol)	Interactive image
ChemSpider	9794
ECHA InfoCard	100.006.886
PubChem CID	10209
UNII	VQ093653DO
CompTox Dashboard (EPA)	DTXSID5023247
InChI InChI=1S/C11H10O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,12-13H,1H3
SMILES Oc2c1ccccc1c(O)c(c2)C
Properties
Chemical formula	C11H10O2
Molar mass	174.199 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Menadiol sodium diphosphate is approved in the UK for treatment and prevention of haemorrhage, mainly in obstructive jaundice (before and after surgery).^[6] Unlike natural, lipophilic forms of vitamin K, menadiol sodium diphosphate does not require bile for absorption, hence the use in obstructive jaundice. A disadvantage is that it takes 24 hours to show effects, though the effects do last for several days. It can cause hemolytic anemia, more commonly in people with glucose 6-phosphate dehydrogenase deficiency^[7] or vitamin E deficiency.^[6]

Menadiol is probably naturally produced by reduction of menadione ("vitamin K₃"; see Quinone § Reduction) as an intermediate in the conversion from K₃ to MK-4.^[8] It can be oxidized in experimental conditions back to menadione.^[9]