M5750

Sigma-Aldrich

Menadione sodium bisulfite

≥95% (TLC)

Synonym(s):
2-Methyl-1,4-naphthoquinone sodium bisulfite
Empirical Formula (Hill Notation):
C11H9NaO5S
CAS Number:
Molecular Weight:
276.24
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

assay

≥95% (TLC)

form

powder

application(s)

cell analysis: suitable

color

white to off-white

solubility

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

originator

Eli Lilly

storage temp.

−20°C

SMILES string

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

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

InChI key

XDPFHGWVCTXHDX-UHFFFAOYSA-M

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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

Packaging

25, 100 g in poly bottle
1 kg in poly bottle

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

Signal Word

Warning

Hazard Statements

hazcat

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

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Into the depths: Techniques for in vitro three-dimensional microtissue visualization
Kabadi PK, et al.
Biotechniques, 59(5), 279-286 (2015)
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...
Katherine W Jordan et al.
PloS one, 7(6), e38722-e38722 (2012-06-21)
Reactive oxygen species (ROS) are a common byproduct of mitochondrial energy metabolism, and can also be induced by exogenous sources, including UV light, radiation, and environmental toxins. ROS generation is essential for maintaining homeostasis by triggering cellular signaling pathways and...
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)
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