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Merck

M9429

Menadione

meets USP testing specifications

Synonym(s):

2-Methyl-1,4-naphthoquinone, Vitamin K3

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About This Item

Empirical Formula (Hill Notation):
C11H8O2
CAS Number:
58-27-5
Molecular Weight:
172.18
UNSPSC Code:
12352205
NACRES:
NA.21
PubChem Substance ID:
24897335
EC Number:
200-372-6
Beilstein/REAXYS Number:
1908453
MDL number:
MFCD00001681

Product Name

Menadione, meets USP testing specifications

InChI key

MJVAVZPDRWSRRC-UHFFFAOYSA-N

InChI

1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

SMILES string

CC1=CC(=O)c2ccccc2C1=O

biological source

synthetic (organic)

agency

USP/NF
meets USP testing specifications

assay

98.5-101.0% dry basis

form

solid

mp

105-107 °C (lit.)

application(s)

pharmaceutical (small molecule)

Quality Level

200

Gene Information

human ... NQO1(1728)

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Application

Menadione has been used:
  • to treat HL-60 cells as positive control for apoptosis for flow cytometry
  • as an oxidative stress inducer in transgenic embryos after 24 h of post fertilization
  • to treat HaCaT cell line, for quantifying total and oxidised glutathione

Biochem/physiol Actions

Menadione is an oxidative stress inducer.

General description

Menadione (Vitamin K3) is the synthetic form of vitamin K. It has the structure similar to vitamin K1 and K2. Vitamin K1, K2 and K3 are biologically active. Water soluble forms of menadiones are used in swine and poultry diets.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

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, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000503876
0000503877
0000503877
0000472448
0000472448

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Nutrient Requirements of Swine, 75-75 (1998)
Dr. Jekyll and Mr. Hyde: Oxidizable phenol-generated reactive oxygen species enhance sulforaphane's antioxidant response element activation, even as they suppress Nrf2 protein accumulation
Bauman BM, et al.
Free Radical Biology & Medicine, 124(3), 532-540 (2018)
Proteomic profile of aminoglutethimide-induced apoptosis in HL-60 cells: role of myeloperoxidase and arylamine free radicals
Khan SR, et al.
Chemico-Biological Interactions, 239, 129-138 (2015)
The Transgenic Zebrafish Display Fluorescence Reflecting the Expressional Dynamics of Dihydrofolate Reductase
Chang WN, et al.
Zebrafish, 14(3), 223-235 (2017)
Juan Lucas Argueso et al.
Genome research, 19(12), 2258-2270 (2009-10-09)
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