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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⁻¹

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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,^[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.
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 ^c Sebrell 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 ^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.
^ "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. PMC 3934721. 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.

Vitamins (A11)

Fat
soluble

A	α-Carotene β-Carotene Retinol^# Tretinoin^#
D	D₂ Ergosterol Ergocalciferol^# D₃ 7-Dehydrocholesterol Previtamin D₃ Cholecalciferol^# 25-hydroxycholecalciferol Calcitriol (1,25-dihydroxycholecalciferol) Calcitroic acid D₄ Dihydroergocalciferol D₅ D analogues Alfacalcidol Dihydrotachysterol Calcipotriol Tacalcitol Paricalcitol
E	Tocopherol Alpha Beta Gamma Delta Tocotrienol Alpha Beta Gamma Delta Tocofersolan
K	Naphthoquinone Phylloquinone (K₁)^# Menaquinones (K₂) Menadione (K₃)^‡ Various (K₄) 4-Amino-2-methyl-1-naphthol (K₅)^‡ 2-Methylnaphthalene-1,4-diamine (K₆) 4-Amino-3-methyl-1-naphthol (K₇)

Water
soluble

Combinations

Multivitamins

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Antihemorrhagics (B02)

Antihemorrhagics
(coagulation)

Systemic

Vitamin K	Phytomenadione (K₁) Menadione (K₃)
Coagulation factors	intrinsic: VIII/(Damoctocog alfa pegol, Efanesoctocog alfa, Efmoroctocog alfa, Moroctocog alfa, Susoctocog alfa, Turoctocog alfa, Valoctocogene roxaparvovec, von Willebrand factor) IX/(Fidanacogene elaparvovec, Nonacog alfa) extrinsic: VII/Eptacog alfa common: X II/Thrombin I/Fibrinogen XIII/Catridecacog combinations: Prothrombin complex concentrate (II, VII, IX, X, protein C and S)
Other systemic	Batroxobin Carbazochrome Concizumab Etamsylate Fostamatinib Marstacimab thrombopoietin receptor agonist Romiplostim Avatrombopag Eltrombopag Lusutrombopag Rafutrombopag

Local

Antifibrinolytics

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