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Menadione (K3)

analytical standard

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C11H8O2
CAS Number:
Molecular Weight:
172.18
Beilstein:
1908453
EC Number:
MDL number:
UNSPSC Code:
12164500
PubChem Substance ID:

grade

analytical standard

CofA

current certificate can be downloaded

feature

standard type fat soluble vitamin

packaging

ampule of 1000 mg

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

105-107 °C (lit.)

application(s)

pharmaceutical (small molecule)
vitamins, nutraceuticals, and natural products

format

neat

storage temp.

2-30°C

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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General description

Menadione (K3) is a fat-soluble vitamin precursor and catabolic product of oral phylloquinone (vitamin k1) in the intestine.
Menadione is a prothrombogenic compound and belongs to the Vitamin K class of compounds, which are necessary for the biosynthesis of prothrombin and other blood clotting factors. It is used as a model quinone in cell culture and in vivo investigations. It is obtained as a catabolic product of phylloquinone and circulating precursor of tissue menaquinone-4 in rats.

Application

Menadione (K3) may be used as an analytical reference standard for the quantification of the analyte in biological fluids using liquid chromatography technique.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Pictograms

Exclamation markEnvironment

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)

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Development of a validated liquid chromatography method for the simultaneous determination of eight fat-soluble vitamins in biological fluids after solid-phase extraction
Chatzimichalakis FP, et al.
Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 805(2), 289-296 (2004)
Arne Søraas et al.
Journal of oral microbiology, 6 (2014-09-11)
The prevalence of infections caused by Cefotaximase-Munich (CTX-M)-type extended-spectrum beta-lactamase-producing Enterobacteriaceae (ESBL-E) has rapidly increased during the past 15 years. Enterobacteriaceae are commonly found in the gastrointestinal tract and long-term intestinal carriage is considered important for the spread of ESBL
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
Didier Buisson et al.
Journal of natural products, 70(6), 1035-1038 (2007-06-15)
Regioselective O-demethylation of the flavones tangeretin (1) and 3-hydroxytangeretin (6) into their 4'-O-demethylated metabolites was performed by using an Aspergillus niger strain. This method serves as a straightforward alternative to multistep synthesis or semisynthesis. The microbial approach is complementary to
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

Protocols

HPLC Analysis of Fat Soluble Vitamins by Normal Phase Chromatography on Ascentis® S

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