Record Information
Version1.0
Creation date2015-10-09 22:31:08 UTC
Update date2017-01-19 02:36:26 UTC
FoodComEx IDPC000524
FoodDB RecordFDB000953
Chemical Information
NameMenadione
DescriptionProthrombogenic 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 Number58-27-5
Structure
Thumb
Synonyms
SynonymSource
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-naftochinonbiospider
2-Methyl-1,4-naphthalendionebiospider
2-Methyl-1,4-naphthalenedionebiospider
2-Methyl-1,4-naphthalenedione, 9CIdb_source
2-Methyl-1,4-naphthochinonbiospider
2-Methyl-1,4-naphthochinon (GERMAN)biospider
2-Methyl-1,4-naphthodionebiospider
2-Methyl-1,4-naphthoquinoneChEBI
2-methyl-1,4-naphthoquinone, 5biospider
2-methylnaphthalene-1,4-dionebiospider
2-Methylnaphthoquinonebiospider
3-Methyl-1,4-naphthoquinonebiospider
Aquakaybiospider
Aquinonebiospider
Hemodalbiospider
Juva-kbiospider
K-thrombylbiospider
K-vitanbiospider
Kaergonabiospider
Kanonedb_source
Kappaxindb_source
Kappaxin (TN)biospider
Karconbiospider
Kareonbiospider
Kativ-gbiospider
Kayklotbiospider
Kaykotbiospider
Kaynonebiospider
Kayquinonedb_source
Kipcabiospider
Kipca-oil solublebiospider
Kipca, oil solublebiospider
Klottonebiospider
Koaxinbiospider
Kolklotbiospider
Memodolbiospider
Menadionbiospider
Menadionebiospider
Menadione (K3)biospider
Menadione (usp)biospider
Menadione [usan:ban]biospider
Menadione semiquinonebiospider
Menadione sodium bisulfitebiospider
Menadione, BAN, USANdb_source
Menadionumbiospider
Menaphthenebiospider
Menaphthonbiospider
Menaphthonebiospider
Menaphtonebiospider
Menaquinone 0biospider
Menaquinone obiospider
Methyl-1,4-naphthalenedionebiospider
Methyl-1,4-naphthoquinonebiospider
Methylnaphthoquinonebiospider
Mitenonbiospider
Mitenonebiospider
MNQbiospider
Naphthoquinone, methyl-biospider
Panosinebiospider
Prokayvitbiospider
Synkaybiospider
Thyloquinonedb_source
Vicasolbiospider
Vikasolbiospider
Vitamin K 3biospider
Vitamin K0biospider
Vitamin k2HMDB
Vitamin K2(0)biospider
Vitamin K3db_source
Vitamin K3 : 2-Methyl-1,4-naphthoquinonebiospider
Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalenebiospider
Chemical FormulaC11H8O2
IUPAC name2-methyl-1,4-dihydronaphthalene-1,4-dione
InChI IdentifierInChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChI KeyMJVAVZPDRWSRRC-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(=O)C2=CC=CC=C2C1=O
Average Molecular Weight172.18
Monoisotopic Molecular Weight172.0524295
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP2.20HANSCH,C ET AL. (1995)
Experimental Water Solubility0.16 mg/mL at 30 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting PointMp 104-105°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 300 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci H500
AKSci J10681
AKSci J40176
AKSci J94454
Cayman Chemical 15950
MetaSci HMDB0001892
Sigma-Aldrich HMDB0001892
Toronto Research Chemicals V676130