Menadione

Menadione^[1]
Names
	Preferred IUPAC name 2-Methylnaphthalene-1,4-dione
	Other names Menaphthone; Vitamin K3; β-Methyl-1,4-naphthoquinone; 2-Methyl-1,4-naphthodione; 2-Methyl-1,4-naphthoquinone
Identifiers
CAS Number	58-27-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28869 ;
ChEMBL	ChEMBL590 ;
ChemSpider	3915 ;
DrugBank	DB00170 ;
ECHA InfoCard	100.000.338
KEGG	D02335 ;
PubChem CID	4055;
UNII	723JX6CXY5 ;
CompTox Dashboard (EPA)	DTXSID4021715 ;
	InChI InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 Key: MJVAVZPDRWSRRC-UHFFFAOYSA-N ; InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 Key: MJVAVZPDRWSRRC-UHFFFAOYAY;
	SMILES O=C\2c1c(cccc1)C(=O)/C(=C/2)C;
Properties
Chemical formula	C11H8O2
Molar mass	172.183 g·mol−1
Appearance	Bright yellow crystals
Density	1.225g/cm3
Melting point	105 to 107 °C (221 to 225 °F; 378 to 380 K)
Solubility in water	Insoluble
Pharmacology
ATC code	B02BA02 (WHO)
Pregnancy; category	Contraindicated (India);
Routes of; administration	Oral; Intravenous; Intramuscular;
Legal status	Generally Rx or withdrawn for human use; approved in animal feed;
Hazards
Flash point	113.8 °C (236.8 °F; 386.9 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	0.5 g/kg (oral, mouse)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Menadione is a synthetic^[3]^[4] organic compound with the formula C₆H₄(CO)₂C₂H(CH₃). It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position.^[5] It is sometimes called vitamin K₃. Use is allowed as a nutritional supplement in animal feed because of its vitamin K activity.

^ The Merck Index, 11th Edition, 5714
^ Cite error: The named reference dui was invoked but never defined (see the help page).
^ "Menadione". go.drugbank.com. Retrieved 2024-09-01.
^ Hirota, Yoshihisa; Tsugawa, Naoko; Nakagawa, Kimie; Suhara, Yoshitomo; Tanaka, Kiyoshi; Uchino, Yuri; Takeuchi, Atsuko; Sawada, Natsumi; Kamao, Maya; Wada, Akimori; Okitsu, Takashi (2013-11-15). "Menadione (vitamin K3) is a catabolic product of oral phylloquinone (vitamin K1) in the intestine and a circulating precursor of tissue menaquinone-4 (vitamin K2) in rats". The Journal of Biological Chemistry. 288 (46): 33071–33080. doi:10.1074/jbc.M113.477356. ISSN 1083-351X. PMC 3829156. PMID 24085302.
^ Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD (2008). Fox (ed.). "Cytotoxicity mechanism of two naphthoquinones (menadione and plumbagin) in Saccharomyces cerevisiae". PLOS ONE. 3 (12): e3999. Bibcode:2008PLoSO...3.3999C. doi:10.1371/journal.pone.0003999. PMC 2600608. PMID 19098979.

Names


Preferred IUPAC name 2-Methylnaphthalene-1,4-dione
Other names Menaphthone; Vitamin K₃; β-Methyl-1,4-naphthoquinone; 2-Methyl-1,4-naphthodione; 2-Methyl-1,4-naphthoquinone
Identifiers
CAS Number	58-27-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28869^N
ChEMBL	ChEMBL590^Y
ChemSpider	3915^Y
DrugBank	DB00170^N
ECHA InfoCard	100.000.338
KEGG	D02335^Y
PubChem CID	4055
UNII	723JX6CXY5^Y
CompTox Dashboard (EPA)	DTXSID4021715
InChI InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3^Y Key: MJVAVZPDRWSRRC-UHFFFAOYSA-N^Y InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 Key: MJVAVZPDRWSRRC-UHFFFAOYAY
SMILES O=C\2c1c(cccc1)C(=O)/C(=C/2)C
Properties
Chemical formula	C₁₁H₈O₂
Molar mass	172.183 g·mol⁻¹
Appearance	Bright yellow crystals
Density	1.225g/cm3
Melting point	105 to 107 °C (221 to 225 °F; 378 to 380 K)
Solubility in water	Insoluble
Pharmacology
ATC code	B02BA02 (WHO)
Pregnancy category	Contraindicated (India)^[2]
Routes of administration	Oral Intravenous Intramuscular
Legal status	Generally Rx or withdrawn for human use; approved in animal feed
Hazards
Flash point	113.8 °C (236.8 °F; 386.9 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	0.5 g/kg (oral, mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references