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Menadiol

Names
Preferred IUPAC name 2-Methylnaphthalene-1,4-diol
Other names 2-Methyl-1,4-naphthalenediol; 2-Methyl-1,4-dihydroxynaphthalene
Identifiers
CAS Number	481-85-6
3D model (JSmol)	Interactive image
ChemSpider	9794
ECHA InfoCard	100.006.886
PubChem CID	10209
UNII	VQ093653DO
CompTox Dashboard (EPA)	DTXSID5023247
InChI InChI=1S/C11H10O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,12-13H,1H3
SMILES Oc2c1ccccc1c(O)c(c2)C
Properties
Chemical formula	C11H10O2
Molar mass	174.199 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

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,
• its various esters, e.g.
  • menadiol diacetate (acetomenaphthone),
  • menadiol dibutyrate,
  • menadiol dimalonate, or
• its various salts, like
  • menadiol sodium diphosphate (Kappadione)
  • menadiol sodium disulfate.

Menadiol sodium diphosphate is approved in the UK for treatment and prevention of haemorrhage, mainly in obstructive jaundice (before and after surgery).

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. It can be oxidized in experimental conditions back to menadione.

• The menadiol core is apparent in the structure of vitamin K.
• Menadiol diacetate
• 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.

• 1-Naphthols
• Vitamin K
• Hydroquinones