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M5625

Sigma-Aldrich

Menadione

crystalline

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Synonym(s):
2-Methyl-1,4-naphthoquinone, Vitamin K3
Empirical Formula (Hill Notation):
C11H8O2
CAS Number:
58-27-5
Molecular Weight:
172.18
Beilstein:
1908453
EC Number:
200-372-6
MDL number:
MFCD00001681
PubChem Substance ID:
24897023
NACRES:
NA.79

biological source

synthetic

Quality Level

200

Assay

≥98.0% (HPLC)

form

crystalline

technique(s)

HPLC: suitable

color

faint green to green-yellow

mp

105-107 °C (lit.)

solubility

oil: soluble

storage temp.

room temp

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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This Item
47775M9429PHR1411
Menadione crystalline

Sigma-Aldrich

M5625

Menadione

Menadione (K3) analytical standard

Supelco

47775

Menadione (K3)

Menadione meets USP testing specifications

Sigma-Aldrich

M9429

Menadione

Menadione Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1411

Menadione

assay

≥98.0% (HPLC)

assay

-

assay

98.5-101.0% dry basis

assay

-

form

crystalline

form

-

form

solid

form

-

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

technique(s)

-

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

color

faint green to green-yellow

color

-

color

-

color

-

mp

105-107 °C (lit.)

mp

105-107 °C (lit.)

mp

105-107 °C (lit.)

mp

105-107 °C (lit.)

Application

Menadione has been used for the generation of reactive oxygen species (ROS), followed by flow cytometry analysis. It has also been used in microbiological evaluation, such as to detect fastidious microorganisms.

Biochem/physiol Actions

Menadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position. Menadione is used as a phosphatase inhibitor and an inhibitor of mitochondrial DNA polymerase γ (pol γ). Menadione can be used as an oxidative injury (free radical generator) inducing agent.
Menadione is an aromatic polycyclic ketone. It serves as a precursor for vitamin K synthesis. Menadione is converted to menaquinone-4, an active metabolite of vitamin K3. Menadione mediates cell death, by inducing the production of reactive oxygen species through the futile redox cycling.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Resp. Sens. 1 - 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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Investigation of cultivable bacteria isolated from longstanding retreatment-resistant lesions of teeth with apical periodontitis
Signoretti Fernanda GC, et al.
Journal of Endodontics, 39(10), 1240-1244 (2013)
Antioxidants can increase melanoma metastasis in mice
Le Gal K, et al.
Science Translational Medicine, 7(308), 308re8-308re8 (2015)
Menadione is a metabolite of oral vitamin K
Thijssen Henk HW, et al.
The British Journal of Nutrition, 95(2), 260-266 (2006)
Menadione triggers cell death through ROS-dependent mechanisms involving PARP activation without requiring apoptosis
Loor G, et al.
Free Radical Biology & Medicine, 49(12), 1925-1936 (2010)
H Thor et al.
The Journal of biological chemistry, 257(20), 12419-12425 (1982-10-25)
The cytotoxic effects of many quinones are thought to be mediated through their one-electron reduction to semiquinone radicals, which subsequently enter redox cycles with molecular oxygen to produce active oxygen species and oxidative stress. The two-electron reduction of quinones to
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