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M5625

Sigma-Aldrich

Menadione

crystalline

Synonym(s):

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

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20 μG
¥3,096.05
50 μG
¥5,521.21

¥3,096.05

Estimated to ship on2025年7月16日Details

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20 μG
¥3,096.05
50 μG
¥5,521.21

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

¥3,096.05

Estimated to ship on2025年7月16日Details

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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

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Show Differences

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T953420928790279
Triethanolamine hydrochloride ≥99.5% (titration)

T1502

Triethanolamine hydrochloride

Triethanolamine hydrochloride BioXtra, ≥99.5% (titration)

T9534

Triethanolamine hydrochloride

Diethanolamine hydrochloride 98%

209287

Diethanolamine hydrochloride

Triethanolamine ≥99.0% (GC)

90279

Triethanolamine

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

200

application(s)

diagnostic assay manufacturing

application(s)

diagnostic assay manufacturing

application(s)

-

application(s)

-

form

crystalline powder

form

powder

form

-

form

liquid, viscous liquid

solubility

water: 0.333 g/mL, clear, colorless

solubility

H2O: 1 M, clear, colorless

solubility

-

solubility

H2O: 1 M, clear, colorless

mp

177-179 °C (lit.)

mp

177-179 °C (lit.)

mp

-

mp

17.9-21 °C (lit.)

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
  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    0000438867
    0000438867
    0000321478
    WXBF3404V
    0000321478

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    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
    Menadione is a metabolite of oral vitamin K
    Thijssen Henk HW, et al.
    The British Journal of Nutrition, 95(2), 260-266 (2006)
    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)
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