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Menadiol

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(Redirected fromVitamin 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 InfoCard100.006.886Edit 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 mass174.199 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Menadiol is an organic compound with the formula C6H4(COH)2(CH)(CH3). It is formally a derivative of p-hydroquinone. The namevitamin K4 can refer to:

  • specifically this compound,[1][2]
  • its variousesters, 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] Unlike natural, lipophilic forms of vitamin K, menadiol sodium diphosphate does not requirebile 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 causehemolytic anemia, more commonly in people withglucose 6-phosphate dehydrogenase deficiency[7] orvitamin E deficiency.[6]

Menadiol is probably naturally produced by reduction ofmenadione ("vitamin K3"; seeQuinone § Reduction) as an intermediate in the conversion from K3 toMK-4.[8] It can be oxidized in experimental conditions back to menadione.[9]

  • The menadiol core is apparent in the structure of vitamin K1.
    The menadiol core is apparent in the structure ofvitamin K1.
  • Menadiol diacetate
    Menadiol diacetate
  • Menadiol dibutyrate
    Menadiol dibutyrate

References

[edit]
  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. ^abcSebrell 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. ^abcdOketch-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. ^ab"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.
Fat
soluble
A
D
E
K (B02B)
Water
soluble
B
C
Combinations
Antihemorrhagics
(coagulation)
Systemic
Vitamin K
Coagulation
factors
Other
systemic
Local
Antifibrinolytics
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