Menadiol

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Vitamin K4
)
Menadiol
Skeletal formula of menadiol
Skeletal formula of menadiol
Ball-and-stick model of menadiol
Ball-and-stick model of menadiol
Names
Preferred IUPAC name
2-Methylnaphthalene-1,4-diol
Other names
2-Methyl-1,4-naphthalenediol; 2-Methyl-1,4-dihydroxynaphthalene
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.006.886 Edit this at Wikidata
UNII
  • InChI=1S/C11H10O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,12-13H,1H3
  • Oc2c1ccccc1c(O)c(c2)C
Properties
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).

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 Quinone § Reduction) as an intermediate in the conversion from K3 to MK-4.[7] It can be oxidized in experimental conditions back to menadione.[8]

  • The menadiol core is apparent in the structure of vitamin K.
    The menadiol core is apparent in the structure of vitamin K.
  • Menadiol diacetate
    Menadiol diacetate
  • Menadiol dibutyrate
    Menadiol dibutyrate

References

  1. S2CID 975055
    .
  2. ^
    ISBN 9780126337631
    .
  3. ISSN 1831-4732
    .
  4. ^
    PMID 28838081
    .
  5. ^ "Kappadione". go.drugbank.com.
  6. ^ "Menadiol Diphosphate Tablets 10mg - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk.
  7. PMID 24489112
    .
  8. S2CID 86263542
    .


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