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Merck

M5750

Menadione sodium bisulfite

synthetic, ≥95% (TLC), Prothrombogenic compound, powder

Synonyme(s) :

2-Methyl-1,4-naphthoquinone sodium bisulfite

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A propos de cet article

Formule empirique (notation de Hill) :
C11H9NaO5S
Numéro CAS:
130-37-0
Poids moléculaire :
276.24
NACRES:
NA.77
PubChem Substance ID:
24897038
UNSPSC Code:
12352200
EC Number:
204-987-0
MDL number:
MFCD00051456

Principaux documents

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Nom du produit

Menadione sodium bisulfite, ≥95% (TLC)

InChI key

XDPFHGWVCTXHDX-UHFFFAOYSA-M

InChI

1S/C11H10O5S.Na/c1-11(17(14,15)16)6-9(12)7-4-2-3-5-8(7)10(11)13;/h2-5H,6H2,1H3,(H,14,15,16);/q;+1/p-1

SMILES string

[Na+].CC1(CC(=O)c2ccccc2C1=O)S([O-])(=O)=O

biological source

synthetic

assay

≥95% (TLC)

form

powder

color

white to off-white

solubility

H2O: ≥50 mg/mL, clear, colorless to faintly yellow

application(s)

cell analysis

originator

Eli Lilly

storage temp.

−20°C

Quality Level

200

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Catégories apparentées

Application

Menadione sodium bisulfite has been used:
  • as a priming agent in tomato for improving salt tolerance
  • to induce reactive oxygen species (ROS) in human lung epithelium BEAS-2B microtissues
  • to induce endogenous superoxide production in mouse C17.2 neural stem cells

Biochem/physiol Actions

Menadione sodium bisulfite is a water-soluble form of menadione, which belongs to the Vitamin K class of compounds. These are necessary for the biosynthesis of prothrombin and other blood clotting factors. Menadione is a prothrombogenic compound and is used as a model quinone in cell culture and in vivo investigations.

Menadione has been shown to affect gap-junctional intercellular communication by mediation of tyrosine phosphorylation. Menadione has demonstrated cytotoxic activity against a variety of cell lines and can induce apoptosis in cultured cells, such as osteoclasts and osteoblasts, via elevation of peroxide and superoxide radical levels.

An HPLC method for detection of menadione sodium bisulfite in multivitamin formulations has been published. A chemiluminescence assay for menadione sodium bisulfite in pharmaceutical preparations and biological fluids has been reported.

Features and Benefits

This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

Water soluble vitamin K3.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
WXBF6268V
WXBF3997V
WXBF2717V
WXBD6773V
WXBF0802

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Consulter la Bibliothèque de documents

Momordica charantia polysaccharides could protect against cerebral ischemia/reperfusion injury through inhibiting oxidative stress mediated c-Jun N-terminal kinase 3 signaling pathway
Gong J, et al.
Neuropharmacology, 9, 123-134 (2015)
Menadione sodium bisulphite (MSB): Beyond seed-soaking. Root pretreatment with MSB primes salt stress tolerance in tomato plants
Jimenez-Arias D, et al.
Environmental and Experimental Botany, 157, 161-170 (2019)
Arit Ghosh et al.
G3 (Bethesda, Md.), 4(2), 349-365 (2013-12-19)
Protein phosphatases are integral components of the cellular signaling machinery in eukaryotes, regulating diverse aspects of growth and development. The genome of the filamentous fungus and model organism Neurospora crassa encodes catalytic subunits for 30 protein phosphatase genes. In this
Gyungsoon Park et al.
Eukaryotic cell, 10(11), 1553-1564 (2011-10-04)
Serine/threonine (S/T) protein kinases are crucial components of diverse signaling pathways in eukaryotes, including the model filamentous fungus Neurospora crassa. In order to assess the importance of S/T kinases to Neurospora biology, we embarked on a global analysis of 86
Dmytro V Gospodaryov et al.
Biochimica et biophysica acta, 1837(11), 1861-1869 (2014-08-16)
An assembled cDNA coding for the putative single-subunit NADH dehydrogenase (NDX) of Ciona intestinalis was introduced into Drosophila melanogaster. The encoded protein was found to localize to mitochondria and to confer rotenone-insensitive substrate oxidation in organello. Transgenic flies exhibited increased
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