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58-27-5 molecular structure
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2-methyl-1,4-dihydronaphthalene-1,4-dione

ChemBase ID: 55
Molecular Formular: C11H8O2
Molecular Mass: 172.18002
Monoisotopic Mass: 172.0524295
SMILES and InChIs

SMILES:
O=C1c2c(C(=O)C=C1C)cccc2
Canonical SMILES:
O=C1C=C(C)C(=O)c2c1cccc2
InChI:
InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChIKey:
MJVAVZPDRWSRRC-UHFFFAOYSA-N

Cite this record

CBID:55 http://www.chembase.cn/molecule-55.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-methyl-1,4-dihydronaphthalene-1,4-dione
IUPAC Traditional name
menadione
Brand Name
Synkavite
Synkayvite
Kappaxin
Klottone
Panosine
Kolklot
Kayklot
Synonyms
Menadione
2-methylnaphthalene-1,4-dione
Vitamin K3
Vitamin K3
2-Methylnaphthoquinone
1,4-Dihydro-1,4-dioxo-2-methylnaphthalene
Aquakay
Aquinone
Hemodal
K-Thrombyl
K-Vitan
Kaergona
Kanone
Kappaxan
Kappaxin
Karcon
Kareon
Kativ-G
Kayklot
Kaykot
Kaynone
Kipca
Kipca-Oil Soluble
Klottone
Koaxin
Kolklot
MNQ
Menadion
Menaphthon
Menaquinone 0
Mitenon
Mitenone
NSC 4170
Panosine
Prokayvit
Synkay
Vitamin K3
Menadione (K3)
β-Methyl-1,4-naphthoquinone
2-Methyl-1,4-naphthodione
2-Methyl-1,4-Naphthalenedione
2-Methyl-1,4-naphthoquinone
Vitamin K 3
Menaphthone
Thyloquinone
Kayquinone
Vitamin K3
Menadione
Menadione
1,4-Dihydro-2-methylnaphthalene-1,4-dione
2-methyl-1,4-naphthoquinone
2-Methyl-1,4-naphthoquinone
2-甲基-1,4-萘醌
维生素 K3
甲萘醌
甲萘醌
甲萘醌 (K3)
2-甲基-1,4-萘醌
CAS Number
58-27-5
EC Number
200-372-6
MDL Number
MFCD00001681
Beilstein Number
1908453
Merck Index
145831
PubChem SID
46505447
24871411
24897335
24897023
160963518
PubChem CID
4055
CHEBI ID
28869
ATC CODE
B02BA02
CHEMBL
590
Chemspider ID
3915
DrugBank ID
DB00170
KEGG ID
D02335
Unique Ingredient Identifier
723JX6CXY5
Wikipedia Title
Menadione

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.936644  H Acceptors
H Donor LogD (pH = 5.5) 1.8898684 
LogD (pH = 7.4) 1.8898674  Log P 1.8898685 
Molar Refractivity 50.5403 cm3 Polarizability 18.667366 Å3
Polar Surface Area 34.14 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.91  LOG S -2.53 
Solubility (Water) 5.04e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Dichloromethane expand Show data source
Dimethylformamide expand Show data source
Ethyl Acetate expand Show data source
Insoluble expand Show data source
Insoluble in water expand Show data source
Methanol expand Show data source
oil: soluble expand Show data source
Apperance
Bright yellow crystals expand Show data source
Pale Yellow Solid expand Show data source
yellow crystalline expand Show data source
Melting Point
102-106 °C expand Show data source
104-107°C expand Show data source
105-107 expand Show data source
105-107 °C(lit.) expand Show data source
105-107°C expand Show data source
105–107 °C expand Show data source
97-99°C expand Show data source
Boiling Point
304.5 °C @ 760mmHg expand Show data source
Flash Point
113.8 °C expand Show data source
Density
1.225g/cm3 expand Show data source
Hydrophobicity(logP)
1.6 expand Show data source
Storage Condition
-20°C expand Show data source
Amber Vial, -20°C Freezer, Under Inert Atmosphere expand Show data source
Room Temperature (15-30°C), Protect from light expand Show data source
Storage Warning
IRRITANT expand Show data source
Irritant/Light Sensitive expand Show data source
Light Sensitive expand Show data source
RTECS
QL9100000 expand Show data source
European Hazard Symbols
X expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-36/37 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
LD50
0.5 g/kg (oral, mouse) expand Show data source
GHS Hazard statements
H301-H315-H319-H335 expand Show data source
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A expand Show data source
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Gene Information
human ... NQO1(1728) expand Show data source
Purity
≥97.0% (HPLC) expand Show data source
97% expand Show data source
98% expand Show data source
Grade
analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Packaging
ampule of 1000 mg expand Show data source
Suitability
meets USP testing specifications expand Show data source
Feature
standard type fat soluble vitamin expand Show data source
Empirical Formula (Hill Notation)
C11H8O2 expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02102259 external link
Yellow crystals
DrugBank - DB00170 external link
Item Information
Drug Groups approved; nutraceutical
Description 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]
Indication The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.
Pharmacology 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 K. 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.
Toxicity Menadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Variable and ranges from 10% to 80%
External Links
Wikipedia
PDRhealth
Selleck Chemicals - S1949 external link
Research Area: Endocrinology
Biological Activity:
Menadione(Vitamin K3), a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone,after alkylation in vivo. Menadione (vitamin K3) is involved as a cofactor in the posttranslational gamma-carboxylation of glutamic acid residues of certain proteins in the body. These proteins include the vitamin K-dependent coagulation factors II (prothrombin), VII (proconvertin), IX (Christmas factor), X (Stuart factor), protein C, protein S, protein Zv and a growth-arrest-specific factor (Gas6). [1]
Sigma Aldrich - M5625 external link
包装
25, 100 g in glass bottle
Biochem/physiol Actions
Menadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position. Menadione is used as a phosphatase inhibitor and an inhibitor of mitochondrial DNA polymerase γ (pol γ). Menadione can be used as an oxidative injury (free radical generator) inducing agent.
Sigma Aldrich - M57405 external link
Packaging
5, 100 g in glass bottle
Sigma Aldrich - 67900 external link
Other Notes
Review: Vitamin K and γ-carboxyglutamate biosynthesis1
Toronto Research Chemicals - V676130 external link
Precursor to verious types of Vitamin K. Used as a micronutrient for livestock and pet foods.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://www.drugbank.ca/drugs/DB00170
  • • Sakamoto, S., et al.: Anal. Bioanal. Chem., 396, 2955 (2010)
  • • Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)
  • • Hu, W., et al.: Anal. Biochem., 398, 245 (2010)
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PATENTS

PATENTS

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INTERNET

INTERNET

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