Menadione | CAS#58-27-5

Menadione
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318184

CAS#: 58-27-5

Description: 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.

Chemical Structure

Menadione

CAS# 58-27-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318184
Name: Menadione
CAS#: 58-27-5
Chemical Formula: C11H8O2
Exact Mass: 172.05
Molecular Weight: 172.183
Elemental Analysis: C, 76.73; H, 4.68; O, 18.58

Price and Availability

Size	Price	Availability
25g	USD 350	2 Weeks
50g	USD 550	2 Weeks
500g	USD 2450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Menadione; Vitamin K3; 2-Methyl-1,4-naphthoquinone; Menaphthone; Thyloquinone; Vitamin K3 sodium bisulfite; Vicasol; Vikasol;Menadione bisulfite;

IUPAC/Chemical Name: 2-methylnaphthalene-1,4-dione

InChi Key: MJVAVZPDRWSRRC-UHFFFAOYSA-N

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

SMILES Code: CC1=CC(=O)C2=CC=CC=C2C1=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Menadione, a naphthoquinone, can be converted to active vitamin K2 in vivo.
In vitro activity:	Conjunctival fibroblasts were incubated for 24 hours. An artificial wound was made and the cells were incubated with fresh medium plus doses of vitamin K3 to be tested. Fibroblast mitogenic activity was statistically decreased in all vitamin K groups; statistical differences were found among vitamin K3 1 mg/mL and higher doses too. Vitamin K3 is able to inhibit fibroblast proliferation. Reference: ScientificWorldJournal. 2014 Jan 8;2014:916713. https://pubmed.ncbi.nlm.nih.gov/24523654/
In vivo activity:	In the second animal model, until day 300, CDC25B mRNA and protein expression levels were slightly lower in primates of the MNU (N-Methyl-N-nitrosourea) + MD (menadione) group compared to animals of the MNU group. However, at day 960 both expression levels were around 40% lower in the animals treated with MD (Figure 4). The animal of MNU group that was treated with MD after tumor development presented a considerable decrease in CDC25B mRNA and protein expression levels at the time of surgical tumor extraction when compared to day 990 and to the nontreated animal (Figure 4). Reference: Therap Adv Gastroenterol. 2020 Jan 11;13:1756284819895435. https://pubmed.ncbi.nlm.nih.gov/35392297/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Ethanol	22.0	127.77
	Water	0.1	0.58
	DMSO	34.7	201.34
	DMF	30.0	174.23
	DMF:PBS (pH 7.2) (1:1)	0.5	2.90

Preparing Stock Solutions

The following data is based on the product molecular weight 172.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Pinilla I, Izaguirre LB, Gonzalvo FJ, Piazuelo E, Garcia-Gonzalez MA, Sanchez-Cano AI, Sopeña F. In vitro vitamin K3 effect on conjunctival fibroblast migration and proliferation. ScientificWorldJournal. 2014 Jan 8;2014:916713. doi: 10.1155/2014/916713. PMID: 24523654; PMCID: PMC3910386. 2. Scott GK, Atsriku C, Kaminker P, Held J, Gibson B, Baldwin MA, Benz CC. Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation. Mol Pharmacol. 2005 Sep;68(3):606-15. doi: 10.1124/mol.105.013474. Epub 2005 Jun 6. PMID: 15939799. 3. Bona AB, Calcagno DQ, Ribeiro HF, Muniz JAPC, Pinto GR, Rocha CAM, Lacreta Junior ACC, de Assumpção PP, Herranz JAR, Burbano RR. Menadione reduces CDC25B expression and promotes tumor shrinkage in gastric cancer. Therap Adv Gastroenterol. 2020 Jan 11;13:1756284819895435. doi: 10.1177/1756284819895435. PMID: 35392297; PMCID: PMC8981514. 4. Kapadia GJ, Soares IAO, Rao GS, Badoco FR, Furtado RA, Correa MB, Tavares DC, Cunha WR, Magalhães LG. Antiparasitic activity of menadione (vitamin K3) against Schistosoma mansoni in BABL/c mice. Acta Trop. 2017 Mar;167:163-173. doi: 10.1016/j.actatropica.2016.12.001. Epub 2016 Dec 23. PMID: 28017859.
In vitro protocol:	1. Pinilla I, Izaguirre LB, Gonzalvo FJ, Piazuelo E, Garcia-Gonzalez MA, Sanchez-Cano AI, Sopeña F. In vitro vitamin K3 effect on conjunctival fibroblast migration and proliferation. ScientificWorldJournal. 2014 Jan 8;2014:916713. doi: 10.1155/2014/916713. PMID: 24523654; PMCID: PMC3910386. 2. Scott GK, Atsriku C, Kaminker P, Held J, Gibson B, Baldwin MA, Benz CC. Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation. Mol Pharmacol. 2005 Sep;68(3):606-15. doi: 10.1124/mol.105.013474. Epub 2005 Jun 6. PMID: 15939799.
In vivo protocol:	1. Bona AB, Calcagno DQ, Ribeiro HF, Muniz JAPC, Pinto GR, Rocha CAM, Lacreta Junior ACC, de Assumpção PP, Herranz JAR, Burbano RR. Menadione reduces CDC25B expression and promotes tumor shrinkage in gastric cancer. Therap Adv Gastroenterol. 2020 Jan 11;13:1756284819895435. doi: 10.1177/1756284819895435. PMID: 35392297; PMCID: PMC8981514. 2. Kapadia GJ, Soares IAO, Rao GS, Badoco FR, Furtado RA, Correa MB, Tavares DC, Cunha WR, Magalhães LG. Antiparasitic activity of menadione (vitamin K3) against Schistosoma mansoni in BABL/c mice. Acta Trop. 2017 Mar;167:163-173. doi: 10.1016/j.actatropica.2016.12.001. Epub 2016 Dec 23. PMID: 28017859.

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1: Halilovic A, Schmedt T, Benischke AS, Hamill CE, Chen Y, Santos JH, Jurkunas UV. Menadione-induced DNA damage leads to mitochondrial dysfunction and fragmentation during rosette formation in Fuchs Endothelial Corneal Dystrophy. Antioxid Redox Signal. 2016 Mar 2. [Epub ahead of print] PubMed PMID: 26935406.

2: Tofolean IT, Ganea C, Ionescu D, Filippi A, Garaiman A, Goicea A, Gaman MA, Dimancea A, Baran I. Cellular determinants involving mitochondrial dysfunction, oxidative stress and apoptosis correlate with the synergic cytotoxicity of epigallocatechin-3-gallate and menadione in human leukemia Jurkat T cells. Pharmacol Res. 2016 Jan;103:300-17. doi: 10.1016/j.phrs.2015.12.013. Epub 2015 Dec 11. PubMed PMID: 26687095.

3: Arslan M, Sevgiler Y, Buyukleyla M, Yardimci M, Yilmaz M, Rencuzogullari E. Sex-related effects of imidacloprid modulated by piperonyl butoxide and menadione in rats. Part II: genotoxic and cytotoxic potential. Drug Chem Toxicol. 2016 Jan;39(1):81-6. doi: 10.3109/01480545.2015.1029049. Epub 2015 Sep 25. PubMed PMID: 25826181.

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