Menadiol

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
  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. ^ a b c 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. ^ a b c d 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.