Skip to Content
Merck
All Photos(4)

Key Documents

M5750

Sigma-Aldrich

Menadione sodium bisulfite

≥95% (TLC)

Synonym(s):

2-Methyl-1,4-naphthoquinone sodium bisulfite

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C11H9NaO5S
CAS Number:
Molecular Weight:
276.24
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

Quality Level

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

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Into the depths: Techniques for in vitro three-dimensional microtissue visualization
Kabadi PK, et al.
Biotechniques, 59(5), 279-286 (2015)
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)
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)

Related Content

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service