FComEx: Menadione (PC000524)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:08 UTC

Update date

2017-01-19 02:36:26 UTC

FoodComEx ID

PC000524

FoodDB Record

FDB000953

Chemical Information

Name

Menadione

Description

Prothrombogenic vitamin (synthetic) A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. -- Pubchem; Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Moreover, menadione supplements have been banned by the FDA because of their high toxicity.; It is sometimes called vitamin K3, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; It is also known as "menaphthone".; It is sometimes called vitamin K3, although derivatives of naphthoquinone without the side chain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin.; K2 vitamers), and hence, is better classified as a provitamin. -- Wikipedia; Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin Kand is also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times.; Menadione is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with a 2-methyl substituent.

CAS Number

58-27-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1, 4-Naphthoquinone, 2-methyl-	biospider
1,4-Naphthalenedione, 2-methyl-	biospider
1,4-Naphthalenedione, 2-methyl-, radical ion(1-)	biospider
1,4-Naphthoquinone, 2-methyl-	biospider
2-Methyl-1,4-naftochinon	biospider
2-Methyl-1,4-naphthalendione	biospider
2-Methyl-1,4-naphthalenedione	biospider
2-Methyl-1,4-naphthalenedione, 9CI	db_source
2-Methyl-1,4-naphthochinon	biospider
2-Methyl-1,4-naphthochinon (GERMAN)	biospider
2-Methyl-1,4-naphthodione	biospider
2-Methyl-1,4-naphthoquinone	ChEBI
2-methyl-1,4-naphthoquinone, 5	biospider
2-methylnaphthalene-1,4-dione	biospider
2-Methylnaphthoquinone	biospider
3-Methyl-1,4-naphthoquinone	biospider
Aquakay	biospider
Aquinone	biospider
Hemodal	biospider
Juva-k	biospider
K-thrombyl	biospider
K-vitan	biospider
Kaergona	biospider
Kanone	db_source
Kappaxin	db_source
Kappaxin (TN)	biospider
Karcon	biospider
Kareon	biospider
Kativ-g	biospider
Kayklot	biospider
Kaykot	biospider
Kaynone	biospider
Kayquinone	db_source
Kipca	biospider
Kipca-oil soluble	biospider
Kipca, oil soluble	biospider
Klottone	biospider
Koaxin	biospider
Kolklot	biospider
Memodol	biospider
Menadion	biospider
Menadione	biospider
Menadione (K3)	biospider
Menadione (usp)	biospider
Menadione [usan:ban]	biospider
Menadione semiquinone	biospider
Menadione sodium bisulfite	biospider
Menadione, BAN, USAN	db_source
Menadionum	biospider
Menaphthene	biospider
Menaphthon	biospider
Menaphthone	biospider
Menaphtone	biospider
Menaquinone 0	biospider
Menaquinone o	biospider
Methyl-1,4-naphthalenedione	biospider
Methyl-1,4-naphthoquinone	biospider
Methylnaphthoquinone	biospider
Mitenon	biospider
Mitenone	biospider
MNQ	biospider
Naphthoquinone, methyl-	biospider
Panosine	biospider
Prokayvit	biospider
Synkay	biospider
Thyloquinone	db_source
Vicasol	biospider
Vikasol	biospider
Vitamin K 3	biospider
Vitamin K0	biospider
Vitamin k2	HMDB
Vitamin K2(0)	biospider
Vitamin K3	db_source
Vitamin K3 : 2-Methyl-1,4-naphthoquinone	biospider
Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalene	biospider

Chemical Formula

C11H8O2

IUPAC name

2-methyl-1,4-dihydronaphthalene-1,4-dione

InChI Identifier

InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

InChI Key

MJVAVZPDRWSRRC-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC(=O)C2=CC=CC=C2C1=O

Average Molecular Weight

172.18

Monoisotopic Molecular Weight

172.0524295

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:28869 )
vitamin K (C05377 )
Fat-soluble vitamins (C05377 )
a vitamin K (CPD-3766 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	2.20	HANSCH,C ET AL. (1995)
Experimental Water Solubility	0.16 mg/mL at 30 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 104-105°	DFC

Foods of Origin