MilliporeSigma
All Photos(3)

Documents

M5625

Sigma-Aldrich

Menadione

crystalline

Sign Into View Organizational & Contract Pricing

Synonym(s):
2-Methyl-1,4-naphthoquinone, Vitamin K3
Empirical Formula (Hill Notation):
C11H8O2
CAS Number:
Molecular Weight:
172.18
Beilstein/REAXYS Number:
1908453
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.79

biological source

synthetic

Quality Level

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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
M94299527147775
Menadione crystalline

M5625

Menadione

-
Menadione meets USP testing specifications

M9429

Menadione

-
Vitamin K1 BioXtra, ≥99.0% (sum of isomers, HPLC), mixture of isomers

95271

Vitamin K1

Premium Grade
Menadione (K3) analytical standard

47775

Menadione (K3)

-
assay

≥98.0% (HPLC)

assay

98.5-101.0% dry basis

assay

≥99.0% (sum of isomers, HPLC)

assay

-

biological source

synthetic

biological source

synthetic (organic)

biological source

synthetic

biological source

-

form

crystalline

form

solid

form

viscous liquid

form

-

storage temp.

room temp

storage temp.

-

storage temp.

2-8°C

storage temp.

2-30°C

solubility

oil: soluble

solubility

-

solubility

-

solubility

-

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.

pictograms

Exclamation markEnvironment

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 7

1 of 7

Hemin from bovine, ≥90%

Sigma-Aldrich

H9039

Hemin

Vitamin K1 BioXtra, ≥99.0% (sum of isomers, HPLC), mixture of isomers

Sigma-Aldrich

95271

Vitamin K1

Vitamin K1 viscous liquid

Sigma-Aldrich

V3501

Vitamin K1

Menaquinone (K2) analytical standard

Supelco

47774

Menaquinone (K2)

Plumbagin phyproof® Reference Substance

PHL80267

Plumbagin

Hemin BioXtra, from Porcine, ≥96.0% (HPLC)

Sigma-Aldrich

51280

Hemin

Vitamin K2

Sigma-Aldrich

V9378

Vitamin K2

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
Efficacy of high intensity diode laser as an adjunct to non-surgical periodontal treatment: a randomized controlled trial
De Micheli G, et al.
Lasers in Medical Science, 26(1), 43-48 (2011)
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)
Joachim Schessl et al.
Brain : a journal of neurology, 132(Pt 2), 452-464 (2009-02-03)
We recently identified the X-chromosomal four and a half LIM domain gene FHL1 as the causative gene for reducing body myopathy, a disorder characterized by progressive weakness and intracytoplasmic aggregates in muscle that exert reducing activity on menadione nitro-blue-tetrazolium (NBT).

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