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M5625

Sigma-Aldrich

Menadione

crystalline

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:
24897023
NACRES:
NA.79
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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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Application

Menadione has been used for the generation of reactive oxygen species (ROS), followed by flow cytometry analysis.[1][2] It has also been used in microbiological evaluation,[3] such as to detect fastidious microorganisms.[4]

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.[5] Menadione is converted to menaquinone-4, an active metabolite of vitamin K3.[6] Menadione mediates cell death, by inducing the production of reactive oxygen species through the futile redox cycling.[5]

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
WXBF3404V
0000321478
WXBF1052V
WXBD7753V
WXBD5296V

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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)
Menadione is a metabolite of oral vitamin K
Thijssen Henk HW, et al.
The British Journal of Nutrition, 95(2), 260-266 (2006)
Antioxidants can increase melanoma metastasis in mice
Le Gal K, et al.
Science Translational Medicine, 7(308), 308re8-308re8 (2015)
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)
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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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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