Menadiol

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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] 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 and is contraindicated in glucose 6-phosphate dehydrogenase deficiency. [7]

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]

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. 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. ↑ "Drugs and haemostasis". Clinical Gate. 2 March 2015.
  8. ↑ 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.
  9. ↑ 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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