Menadiol

Last updated
Menadiol
Skeletal formula of menadiol Menadiol.svg
Skeletal formula of menadiol
Ball-and-stick model of menadiol Menadiol-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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:

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]

Related Research Articles

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References

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  2. 1 2 3 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. 1 2 3 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.