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M5750

Menadione sodium bisulfite

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

Synonym(s):

2-Methyl-1,4-naphthoquinone sodium bisulfite

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About This Item

Empirical Formula (Hill Notation):
C11H9NaO5S
CAS Number:
130-37-0
Molecular Weight:
276.24
NACRES:
NA.77
PubChem Substance ID:
24897038
UNSPSC Code:
12352200
EC Number:
204-987-0
MDL number:
MFCD00051456
Assay:
≥95% (TLC)
Form:
powder
Quality level:
200
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Product Name

Menadione sodium bisulfite, ≥95% (TLC)

biological source

synthetic

Quality Level

200

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

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.

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pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

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

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
048K1372
087K0737
047K0699
116K0749
047K1562

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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
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