Menadiol

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
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
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).
Infobox references

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. Fiore LD, et al. (2001). "Anaphylactoid reactions to vitamin K". Journal of Thrombosis and Thrombolysis. 11 (2): 175–183. doi:10.1023/A:1011237019082. ISSN 0929-5305. PMID 11406734. S2CID 975055.
  2. Sebrell WH, et al. (1971). The vitamins; chemistry, physiology, pathology, methods (2nd ed.). Academic Press. p. 443. ISBN 9780126337631.
  3. "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. 2008. doi:10.2903/j.efsa.2008.822. ISSN 1831-4732.
  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. doi:10.1093/nutrit/nux022. ISSN 0029-6643. PMID 28838081.
  5. "Kappadione". go.drugbank.com.
  6. "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. doi:10.1194/jlr.R045559. ISSN 0022-2275. PMC 3934721. PMID 24489112.
  8. Weber F, Rüttimann A (2012). "Vitamin K". Ullmann's Encyclopedia Of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o27_o08. S2CID 86263542.
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