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Merck
CN

M57405

Menadione

98%

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
EC Number:
200-372-6
UNSPSC Code:
12352200
PubChem Substance ID:
329818021
Beilstein/REAXYS Number:
1908453
MDL number:
MFCD00001681

Key Documents

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InChI key

MJVAVZPDRWSRRC-UHFFFAOYSA-N

InChI

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

SMILES string

CC1=CC(=O)c2ccccc2C1=O

biological source

synthetic

assay

98%

form

powder

technique(s)

HPLC: suitable

color

yellow to yellow-green

mp

105-107 °C (lit.)

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pictograms

Exclamation markEnvironment
GHS07,GHS09

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
S54608
S46517
06612TH
05428KH
13307HH

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Dipankar Koley et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(29), 11522-11527 (2012-06-09)
Oxidative stress induced in live HeLa cells by menadione (2-methyl-1,4-napthaquinone) was studied in real time by scanning electrochemical microscopy (SECM). The hydrophobic molecule menadione diffuses through a living cell membrane where it is toxic to the cell. However, in the
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
H H Thijssen et al.
The British journal of nutrition, 75(1), 121-127 (1996-01-01)
We measured the vitamin K status in postmortem human tissues (brain, heart, kidney, liver, lung, pancreas) to see if there is a tissue-specific distribution pattern. Phylloquinone (K1) was recovered in all tissues with relatively high levels in liver, heart and
Y Usui et al.
The American journal of clinical nutrition, 51(5), 846-852 (1990-05-01)
Vitamin K deficiency has been reported in patients who were treated with antibiotics and placed on poor diets after surgery. High-performance liquid chromatography (HPLC) was used to study the influence of dietary intake on vitamin K concentrations in surgical patients
B Wermuth et al.
Biochemical pharmacology, 35(8), 1277-1282 (1986-04-15)
Enzymes catalyzing the two-electron reduction of quinones to hydroquinones are thought to protect the cell against quinone-induced oxidative stress. Using menadione as a substrate, carbonyl reductase, a cytosolic, monomeric oxidoreductase of broad specificity for carbonyl compounds, was found to be
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