Menadiol

Menadiol
Skeletal formula 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
CAS Number	481-85-6;
3D model (JSmol)	Interactive image;
ChemSpider	9794;
ECHA InfoCard	100.006.886
PubChemCID	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	174.199g·mol−1
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). Infobox references

Menadiolis an organic compound with the formula C₆H₄(COH)₂(CH)(CH₃). It is formally a derivative of p-hydroquinone.The namevitamin K₄can 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]

Menadiol is probably naturally produced by reduction ofmenadione( "vitamin K₃";seeQuinone § Reduction) as an intermediate in the conversion from K₃toMK-4.^[7]It can be oxidized in experimental conditions back to menadione.^[8]

The menadiol core is apparent in the structure ofvitamin K.
Menadiol diacetate
Menadiol dibutyrate

References

^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.
^^a ^b ^cSebrell WH, et al. (1971).The vitamins; chemistry, physiology, pathology, methods(2nd ed.). Academic Press. p. 443.ISBN 9780126337631.
^"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.
^^a ^b ^c ^dOketch-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.
^"Kappadione".go.drugbank.com.
^"Menadiol Diphosphate Tablets 10mg - Summary of Product Characteristics (SmPC) - (emc)".www.medicines.org.uk.
^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.PMC3934721.PMID 24489112.
^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] 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.

[:0-2] 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.

[:1-4] 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.PMC3934721.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.

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