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M9429

Sigma-Aldrich

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
Beilstein:
1908453
EC Number:
200-372-6
MDL number:
MFCD00001681
UNSPSC Code:
12352205
PubChem Substance ID:
24897335
NACRES:
NA.21
Pricing and availability is not currently available.

biological source

synthetic (organic)

Quality Level

200

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)

SMILES string

CC1=CC(=O)c2ccccc2C1=O

InChI

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

InChI key

MJVAVZPDRWSRRC-UHFFFAOYSA-N

Gene Information

human ... NQO1(1728)

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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.[1]

Application

Menadione has been used:
  • to treat HL-60 cells as positive control for apoptosis for flow cytometry[2]
  • as an oxidative stress inducer in transgenic embryos after 24 h of post fertilization[3]
  • to treat HaCaT cell line, for quantifying total and oxidised glutathione[4]

Biochem/physiol Actions

Menadione is an oxidative stress inducer.[3]

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

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 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

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Certificates of Analysis (COA)

Lot/Batch Number
0000388063
0000388063
0000389816
0000359716
0000322060

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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)
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)
Nutrient Requirements of Swine, 75-75 (1998)
Juan Lucas Argueso et al.
Genome research, 19(12), 2258-2270 (2009-10-09)
Bioethanol is a biofuel produced mainly from the fermentation of carbohydrates derived from agricultural feedstocks by the yeast Saccharomyces cerevisiae. One of the most widely adopted strains is PE-2, a heterothallic diploid naturally adapted to the sugar cane fermentation process
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Questions

  1. What is the solubility of product M9429, Menadione?

    1 answer

    1. The solubility of product M9429, Menadione, is as follows:

      1.It is soluble in chloroform (100 mg/ml), with heating as needed, yielding a clear to slightly hazy, yellow-green solution.
      2.Menadione is also soluble in DMSO (1 mg/ml) and in ethanol (16 mg/ml).

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