Menadion

Structural formula
General
Non-proprietary name	Menadion
other names	2-methyl-1,4-naphthoquinone; Vitamin K 3 ;
Molecular formula	C 11 H 8 O 2
External identifiers / databases
EC number	200-372-6
ECHA InfoCard	100,000,338
PubChem	4055
ChemSpider	3915
DrugBank	DB00170
Wikidata	Q192471
Drug information
ATC code	B02 BA02
properties
Molar mass	172.18 g · mol -1
Physical state	firmly
Melting point	105-107 ° C
solubility	almost insoluble in water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Menadione belongs to the group of K vitamins and is also known as vitamin K ₃ .

Extraction and presentation

Menadione is represented by the oxidation of 2-methylnaphthalene with chromic acid or nitric acid .

properties

Menadione is insensitive to oxygen . Decomposition takes place through light, alkalis , strong acids and reducing substances.

use

Menadione was previously used temporarily in a water-soluble form as K ₃ sodium hydrogen sulfite or diphosphate. Vitamin K ₃ in solid form irritates the respiratory tract and the skin. Its use is avoided because of its toxic effects and the naturally occurring phylloquinone is given instead. Menadione is banned for human consumption, but it is still allowed as pet food. Contrary to earlier assumptions and in contrast to the naturally occurring K vitamins, vitamin K _{3 was shown} in animal experiments (calves fed with coumarin- containing sweet clover) to be ineffective with regard to restoring the ability to clot blood.

Individual evidence

↑ Menadion data sheet at AlfaAesar, accessed on February 26, 2010 ( PDF )(JavaScript required) . .

↑ Data menadione from Acros, accessed on 26 February 2010 .

↑ ^a ^b Data sheet Menadione from Sigma-Aldrich , accessed on April 9, 2011 ( PDF ).

^ Heinz-Gerhard Franck, Jürgen W. Stadelhofer: Industrial Aromatic Chemistry Raw Materials Processes Products . Springer-Verlag, 1987, ISBN 978-3-662-07875-4 , pp. 348 ( limited preview in Google Book search).

↑ ^a ^b A.D. Alstad, HH Casper, LJ Johnson: Vitamin K treatment of sweet clover poisoning in calves. In: J. of Am. Vet. Med. As. 1985 , 187 (7) , 729-731

↑ Federal Gazette No. 59

[ALFA-1] Menadion data sheet at AlfaAesar, accessed on February 26, 2010 ( PDF )(JavaScript required) . .

[2] Data menadione from Acros, accessed on 26 February 2010 .

[Sigma-3] Data sheet Menadione from Sigma-Aldrich , accessed on April 9, 2011 ( PDF ).

[Heinz-Gerhard_Franck,_Jürgen_W._Stadelhofer-4] Heinz-Gerhard Franck, Jürgen W. Stadelhofer: Industrial Aromatic Chemistry Raw Materials Processes Products . Springer-Verlag, 1987, ISBN 978-3-662-07875-4 , pp. 348 ( limited preview in Google Book search).

[Alstad-5] A.D. Alstad, HH Casper, LJ Johnson: Vitamin K treatment of sweet clover poisoning in calves. In: J. of Am. Vet. Med. As. 1985 , 187 (7) , 729-731

[6] Federal Gazette No. 59