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58-27-5 (Menadione)

1

Identification

Menadione Menadione
Name Menadione
Formula C11H8O2
MW 172.18
CAS No. 58-27-5
EINECS 200-372-6
Smiles O=C(C(C)=C1)C(C=CC=C2)=C2C1=O
Synonyms 2-Methyl-1,4-naphthoquinone; Vitamin K2(0); Vitamin K3; 2-Methyl-1,4-dihydronaphthalene-1,4-dione; 2-methylnaphthalene-1,4-dione
InChI InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
2

Introduction

Menadione, a synthetic naphthoquinone, can be converted to active vitamin K2 in vivo. Target: Others Menadione (Vitamin K3) is a synthetic analogue of of 1,4-naphthoquinone with a methyl group in the 2-position.

Background Information

Menadione(Vitamin K3), a fat-soluble compound, is an inhibitor of Cdc25 phosphatase and mitochondrial DNA polymerase γ (pol γ), used as a nutritional supplement. ......by AbMole BioScience
Synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2 (menaquinone) after alkylation in vivo. The 1,4-naphthoquinone (NQ) moiety can form redox isomers by accepting one or two electrons respectively. The quinone redox cycling ability leads to the generation of reactive oxygen species (ROS) as well as arylation reactions. Anticancer compound. Apoptosis inducer in various cultured cells including leukemia through several modes of action. Free radical generator. Produces peroxide and superoxide radicals (ROS) leading to mitochondrial dysfunction. Cell cycle inhibitor. Glutathione (GSH) depletion results by direct arylation of cellular thiols. Once GSH is depleted, cellular macromolecules start to be alkylated, resulting in their inactivation. Protein tyrosine phosphatase inhibitor. Inhibitor of mitochondrial DNA polymerase γ. Inhibitor of indoleamine 2,3-dioxygenase (IDO) with an IC50 of ~1μM. ......by Adipogen Corporation
Menadione shows vitamin K activity, used as a nutritional supplement. ......by BOC Sciences
Menadione is an inhibitor of indoleamine2,3-dioxygenase (IDO) (IC₅₀ ~ 1 µM). It induces apoptosis via elevation of peroxide radical levels. Cytotoxic in various cell lines. ......by BioVision, Inc.,
Menadione is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. ......by MedKoo Biosciences, Inc.
Menadione is a dietary nutrient essential for the normal biosynthesis of factors that are required for blood clotting. Menadione is a synthetic chemical compound sometimes used as a nutritional supplement because of its vitamin K activity. It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position. It has also been shown to inhibit cell growth. Vitamin K3 is a synthetic form of vitamin K that acts as a precursor to vitamin K2. It is capable of both redox cycling and arylating nucleophilic substrates by Michael addition and has been used as a model bifunctional quinone to study cellular stress induction. ......by MedKoo Biosciences, Inc.
Menadione(Vitamin K3), a fat-soluble compound, is an inhibitor of Cdc25 phosphatase and mitochondrial DNA polymerase γ (pol γ), used as a nutritional supplement. ......by Selleck Chemicals LLC
A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:Light yellow to yellow Solid EBNumber:EB000012534

Storage condition

Solubility

DMSO 35 mg/mL; Water <1 mg/mL by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 34 mg/mL (197.46 mM); Ethanol34 mg/mL (197.46 mM); Water<1 mg/mL (<1 mM) by Selleck Chemicals LLC
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Mechanism and Indication

Signaling Pathways Others
Target Others
Research Area Others
Indications
6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Menadione - Launched
7

Safety Data of Menadione

Hazard Symbols : Xn
Risk Statements : R22;R36/37/38;R43
Safety Statements : S24;S26;S37/39
RTECS : QL9100000
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AbMole BioScience USA
Adipogen Corporation USA
Ark Pharm, Inc. USA
BOC Sciences
BioVision, Inc., USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 500mg/USD72();1g/USD108() USA
Carbosynth Limited
Cayman Chemical Company USA
Chemos GmbH Germany
Chiron AS Norway
LKT Laboratories Inc. USA
MedChemexpress Co., Ltd. 500mg/USD72();1g/USD108() USA
MedKoo Biosciences, Inc. USA
MedKoo Biosciences, Inc. USA
Selleck Chemicals LLC 50mg/USD97(In stock);10mM/1mLIn DMSO/USD130(In stock) USA
Shanghai Entropy Chemical Co., Ltd CHINA
Shanghai Haoyuan Chemexpress Co., Ltd. 500mg/USD72();1g/USD108() China
Target Molecule Corp. 2mg/USD20();10mg/USD43();50mg/USD89();200mg/USD122() USA
Wuhan Kemi-works Chemical Co., Ltd. China
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Related Products

Other Forms of 58-27-5

Name CAS No Formula MW
Menadione bisulfite (sodium) 130-37-0 C11H9NaO5S 276.24
Menadione bisulfite 130-36-9 C11H10O5S 254.26

Recommended Compounds in Others

Name CAS No Formula MW
(R)-(+)-Etomoxir (sodium salt) 828934-41-4 C15H18ClNaO4 320.74
Dictamine 484-29-7 C12H9NO2 199.21
3,3',5-Triiodo-L-thyronine (sodium) 55-06-1 C15H11I3NNaO4 672.9553
Fabomotizole (hydrochloride) 173352-39-1 C15H22ClN3O2S 343.8721
FPH2 957485-64-2 C14H16ClN5O2S 353.83
α-Tocopherol (phosphate) 38976-17-9 C29H51O5P 510.69
BAMB-4 891025-25-5 C15H12N2O2 252.27
LDN-27219 312946-37-5 C20H16N4O2S2 408.5
ISO-1 478336-92-4 C12H13NO4 235.24
Aurothioglucose 12192-57-3 C6H11AuO5S 392.18
Oxybenzone 131-57-7 C14H12O3 228.24
ITX3 347323-96-0 C22H17N3OS 371.45
Cardiogreen 3599-32-4 C43H47N2NaO6S2 774.96
Skp2 Inhibitor C1 432001-69-9 C18H13BrN2O4S2 465.34
INH1 313553-47-8 C18H16N2OS 308.4
PF6-AM 1268491-69-5 C33H31BO12 630.4
XEN445 1515856-92-4 C18H17F3N2O3 366.33
Disperse Blue 148 52239-04-0 C19H19N5O4S 413.45026
Solvent Blue 35 17354-14-2 C22H26N2O2 350.454
CID-797718 370586-05-3 C12H11NO3 217.2206

Recommended Compounds in Same Indication

Name CAS No Formula MW
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Route of Synthesis

12

References

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More Information

Menadione

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