vitamin K3
a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin k2, menaquinone, after alkylation in vivo. Prothrombogenic vitamin (synthetic) A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. -- Pubchem; Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Moreover, menadione supplements have been banned by the FDA because of their high toxicity.; It is sometimes called vitamin K3, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; It is also known as "menaphthone".; It is sometimes called vitamin K3, although derivatives of naphthoquinone without the side chain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin.; K2 vitamers), and hence, is better classified as a provitamin. -- Wikipedia; Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin K. Also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times.; Menadione is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with a 2-methyl substituent.
  • Jiangyin Healthway
    • Jiangyin Healthway International Trade Co.
      Independent Ingredients Supplier
      We provide custom synthesis and contract manufacturing from milligrams to metric tonnes.
      Jiangyin Healthway International Trade Co., Ltd is a professional company, main engaged in manufacturing and exporting aroma chemicals ,food additives , cosmetic ingredient ,pharmaceutical intermediates & other fine chemicals; especially on aroma chemicals , as the major manufacturer of heterocyclic and sulphur aroma compounds , we are the leading independent ingredients supplier to the flavour and fragrance industries in China, can offer hundreds of different high quality aroma chemicals.
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      For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
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      22-90275 VITAMIN K3, Kosher
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      Tokyo Chemical Industry Co., Ltd. (TCI) is a leading worldwide manufacturer of specialty organic chemicals founded in 1946. TCI provides organic laboratory chemicals as well as pharmaceutical, cosmetic and functional materials. More than 60 years of synthesis experience and multi-purpose plants enable TCI to offer more than 27,000 products as well as custom synthesis. TCI established overseas facilities in North America, Europe, China and India to serve customers worldwide.
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      M0373 2-Methyl-1,4-naphthoquinone
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2-methylnaphthalene-1,4-dione (Click)
CAS Number: 58-27-5Picture of molecule
ECHA EINECS - REACH Pre-Reg: 200-372-6
Nikkaji Web: J4.591H
Beilstein Number: 1908453
MDL: MFCD00001681
XlogP3: 2.20 (est)
Molecular Weight: 172.18316000
Formula: C11 H8 O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: masking agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 107.00 °C. @ 760.00 mm Hg
Boiling Point: 304.50 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.001000 mm/Hg @ 25.00 °C. (est)
Flash Point: 237.00 °F. TCC ( 113.80 °C. ) (est)
logP (o/w): 2.200
Soluble in:
 water, 160 mg/L @ 30 °C (exp)
 water, 793.8 mg/L @ 25 °C (est)
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Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: masking agents
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BOC Sciences
For experimental / research use only.
Menadione >98%
Odor: characteristic
Use: Menadione shows vitamin K activity, used as a nutritional supplement.
For experimental / research use only.
2-Methyl-1,4-naphthoquinone (GC) ≥90%
Foodchem International
Vitamin K3
Graham Chemical
Vitamin K3
Jiangyin Healthway
Vitamin K3
New functional food ingredients
2-Methyl-1,4 Napthoquinone
Penta International
VITAMIN K3, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
vitamin K3 ≥98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Menadione 98%
For experimental / research use only.
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Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-chicken LDLo  100 mg/kg
Proceedings of the Society for Experimental Biology and Medicine. Vol. 43, Pg. 125, 1940.

intraperitoneal-mouse LD50  50 mg/kg
National Technical Information Service. Vol. AD691-490

oral-mouse LD50  500 mg/kg
Proceedings of the Society for Experimental Biology and Medicine. Vol. 43, Pg. 125, 1940.

oral-rabbit LDLo  230 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 111, 1942.

intraperitoneal-rat LD50  75 mg/kg
Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Dermal Toxicity:
subcutaneous-mouse LD50 138 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 75, Pg. 111, 1942.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: masking agents
Recommendation for menadione usage levels up to:
 not for fragrance use.
Recommendation for menadione flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Scientific Opinion on the safety and efficacy of vitamin K3 (menadione sodium bisulphite and menadione nicotinamide bisulphite) as a feed additive for all animal species
View page or View pdf
EPI System: View search
Daily Med: search
NLM Hazardous Substances Data Bank: Search
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA Substance Registry Services (TSCA): 58-27-5
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 4055
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
Chemidplus: 0000058275
RTECS: QL9100000 for cas# 58-27-5
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NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 58-27-5
Pubchem (cid): 4055
Pubchem (sid): 134971654
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
Golm Metabolome Database: Search
KEGG (GenomeNet): C05377
HMDB (The Human Metabolome Database): HMDB01892
FooDB: FDB000953
Export Tariff Code: 2936.29.5050
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
•menadione, nf (vit k3)...avail in oral admin in tablets containing 2, 5, or 10 mg, & as sterile soln of menadione in oil (usually 2, 10, or 25 mgml) designed for im admin. •menadione sodium bisulfite, nf (hykinone)...white crystalline, hygroscopic powder. ...sol in water...marketed in 5-mg tablets & in ampuls5-10 mgml. menadiol sodium diphosphate injection, nf (kappadione, synkavite)...ampuls...5, 10, or 37.5 mgml. menadiol sodium diphosphate tablets, nf...5 mg... •menadiol sodium diphosphate injection, nf (kappadione, synkavite), is marketed in ampuls containing 5, 10, or 37.5 mgml. menadiol sodium diphosphate tablets, nf, contain 5 mg of salt for oral use. •commercially significant forms are menadione sodium bisulfite and menadione dimethyl pyrimidinol. •menadione is available as a 2, 5, and 10 mg tablet and as a 2 and 10 mgml injection (in oil). •trade names for menadione include: aquakay, aquinone, austrovit-k depot, hemodal, k-thrombyl, k-vitan, kaergona, kanone, kaom belgarum, kappaxan, kappaxin, karanum, karcon, kareon, kativ-g, kavitamin, kayklot, kaykot, kayquinone, kipca, kipca-oil soluble, klottone, koaxin, kolklot, menadion, menaphthon, menaphthone, menaquinone 0, mitenon, mitenone, mnq, neo-zimema-k, panosine, prokayvit, synkay, thyloquinone, vikaman, vita-noxi k, and vitavel-k.
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Potential Blenders and core components note
None Found
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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 menaquinone O
1,4-naphthalenedione, 2-methyl-
1,4-naphthoquinone, 2-methyl-
 vitamin K3
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PubMed: External mitochondrial NADH-dependent reductase of redox cyclers: VDAC1 or Cyb5R3?
PubMed: Assessment of Aerobic and Respiratory Growth in the Lactobacillus casei Group.
PubMed: Anti-tumor effects of novel 5-O-acyl plumbagins based on the inhibition of mammalian DNA replicative polymerase activity.
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PubMed: Vitamin K metabolism: Current knowledge and future research.
PubMed: Selection of mutants tolerant of oxidative stress from respiratory cultures of Lactobacillus plantarum C17.
PubMed: Dispersive liquid-liquid microextraction for the determination of vitamins D and K in foods by liquid chromatography with diode-array and atmospheric pressure chemical ionization-mass spectrometry detection.
PubMed: Rapeseed oil-rich diet alters in vitro menadione and nimesulide hepatic mitochondrial toxicity.
PubMed: Synergistic cytotoxicity induced by α-solanine and α-chaconine.
PubMed: Specific dietary carbohydrates differentially influence the life span and fecundity of Drosophila melanogaster.
PubMed: Small colony variants (SCVs) of Staphylococcus aureus--a bacterial survival strategy.
PubMed: Antimutagenic and antioxidant properties of plumbagin and other naphthoquinones.
PubMed: Screening test for rapid food safety evaluation by menadione-catalysed chemiluminescent assay.
PubMed: A nonribosomal peptide synthetase mediates siderophore production and virulence in the citrus fungal pathogen Alternaria alternata.
PubMed: Respiratory capacity of the Kluyveromyces marxianus yeast isolated from the mezcal process during oxidative stress.
PubMed: Roles for SKN7 response regulator in stress resistance, conidiation and virulence in the citrus pathogen Alternaria alternata.
PubMed: Vitamin E decreases extra-hepatic menaquinone-4 concentrations in rats fed menadione or phylloquinone.
PubMed: Dietary intake of menaquinone-4 may determine hepatic and pancreatic menaquinone-4 in chickens.
PubMed: The NADPH oxidase-mediated production of hydrogen peroxide (H(2)O(2)) and resistance to oxidative stress in the necrotrophic pathogen Alternaria alternata of citrus.
PubMed: Adaptive stress response to menadione-induced oxidative stress in Saccharomyces cerevisiae KNU5377.
PubMed: Inhibition of the bioactivation of the neurotoxin MPTP by antioxidants, redox agents and monoamine oxidase inhibitors.
PubMed: In vitro biotransformation and investigation of metabolic enzymes possibly responsible for the metabolism of bisdesoxyolaquindox in the liver fractions of rats, chicken, and pigs.
PubMed: A polyacetylene from Gymnaster koraiensis exerts hepatoprotective effects in vivo and in vitro.
PubMed: Antioxidant effectiveness of coffee extracts and selected constituents in cell-free systems and human colon cell lines.
PubMed: The metabolism and N-oxide reduction of olaquindox in liver preparations of rats, pigs and chicken.
PubMed: The role of reactive oxygen species in the induction of Ty1 retrotransposition in Saccharomyces cerevisiae.
PubMed: The effect of pretreatment or combined treatment of quercetin on menadione toxicity in rat primary mixed glial cells in vitro.
PubMed: Characterization of a nitroreductase with selective nitroreduction properties in the food and intestinal lactic acid bacterium Lactobacillus plantarum WCFS1.
PubMed: Novel cytotoxicity test based on menadione-catalyzed H2O2 productivity for food safety evaluation.
PubMed: Rapid detection of cytotoxicity of food additives and contaminants by a novel cytotoxicity test, menadione-catalyzed H(2)O (2) production assay.
PubMed: Spectrofluorimetric study of the beta-cyclodextrin:vitamin K3 complex and determination of vitamin K3.
PubMed: Impact of delphinidin on the maintenance of DNA integrity in human colon carcinoma cells.
PubMed: The isothiocyanate class of bioactive nutrients covalently inhibit the MEKK1 protein kinase.
PubMed: Study on the electrochemiluminescent behavior of menadione sodium bisulfite in presence of luminol.
PubMed: Enhancing survival of Escherichia coli by increasing the periplasmic expression of Cu,Zn superoxide dismutase from Saccharomyces cerevisiae.
PubMed: Evaluation of the probe dihydrocalcein acetoxymethylester as an indicator of reactive oxygen species formation and comparison with oxidative DNA base modification determined by modified alkaline elution technique.
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PubMed: Equol: a comparison of the effects of the racemic compound with that of the purified S-enantiomer on the growth, invasion, and DNA integrity of breast and prostate cells in vitro.
PubMed: [Menadione-catalyzed luminol chemiluminescence assay for the rapid detection of viable bacteria].
PubMed: Modulation of oxidative cell damage by reconstituted mixtures of phenolic apple juice extracts in human colon cell lines.
PubMed: In vivo relevance of two critical levels for NAD(P)H:quinone oxidoreductase (NQO1)-mediated cellular protection against electrophile toxicity found in vitro.
PubMed: Selective growth-inhibiting effects of compounds identified in Tabebuia impetiginosa inner bark on human intestinal bacteria.
PubMed: Menadione-catalyzed luminol chemiluminescence assay for the rapid detection of viable bacteria in foods under aerobic conditions.
PubMed: Electrochemical evaluation of the inhibitory effects of weak acids on Zygosaccharomyces bailii.
PubMed: Effect of menadione sodium bisulfite, an inducer of plant defenses, on the dynamic of banana phytoalexin accumulation during pathogenesis.
PubMed: Stress situations induce cyanide-resistant respiration in spoilage yeasts.
PubMed: Rapid identification of viable Escherichia coli subspecies with an electrochemical screen-printed biosensor array.
PubMed: Effect of menadione (vitamin K3) addition on lipid oxidation and tocopherols content in plant oils.
PubMed: Paraquat and menadione exposure of rainbow trout (Oncorhynchus mykiss)--studies of effects on the pentose-phosphate shunt and thiamine levels in liver and kidney.
PubMed: Black cohosh (Cimicifuga racemosa L.) protects against menadione-induced DNA damage through scavenging of reactive oxygen species: bioassay-directed isolation and characterization of active principles.
PubMed: Gamma-tocopherol is less effective than alpha-tocopherol in preventing oxidant-induced sister chromatid exchanges in Chinese hamster V79 cells.
PubMed: Efficient production of menaquinone (vitamin K2) by a menadione-resistant mutant of Bacillus subtilis.
PubMed: Influence of added menadione (vitamin K3) on dissolution and dimerization of tocopherols and autoxidation of triacylglycerols during storage of plant oils.
PubMed: Effects of dietary vitamin K on survival, growth, and tissue concentrations of phylloquinone (PK) and menaquinone-4 (MK-4) for juvenile abalone, Haliotis discus hannai Ino.
PubMed: Mechanism of protection by the flavonoids, quercetin and rutin, against tert-butylhydroperoxide- and menadione-induced DNA single strand breaks in Caco-2 cells.
PubMed: Role of aldehyde oxidase in the hepatic in vitro metabolism of 3-methylindole in pigs.
PubMed: Antimutagenic effects and possible mechanisms of action of vitamins and related compounds against genotoxic heterocyclic amines from cooked food.
PubMed: UVA1 radiation triggers two different final apoptotic pathways.
PubMed: Bone structure and strength at different ages in laying hens and effects of dietary particulate limestone, vitamin K and ascorbic acid.
PubMed: Hydrogen peroxide causes RAD9-dependent cell cycle arrest in G2 in Saccharomyces cerevisiae whereas menadione causes G1 arrest independent of RAD9 function.
PubMed: Toxicity of linoleic acid hydroperoxide to Saccharomyces cerevisiae: involvement of a respiration-related process for maximal sensitivity and adaptive response.
PubMed: Immortalized hepatocytes as in vitro model systems for toxicity testing: the comparative toxicity of menadione in immortalized cells, primary cultures of hepatocytes and HTC hepatoma cells.
PubMed: Effects of bio-normalizer (a food supplementation) on free radical production by human blood neutrophils, erythrocytes, and rat peritoneal macrophages.
PubMed: Cytotoxicity of retinoic acid, menadione and aflatoxin B(1) in rat liver slices using Netwell inserts as a new culture system.
PubMed: Production and application of monoclonal antibodies specific to pyrroloquinoline quinone.
PubMed: Pathology of 2-alkyl and 2-hydroxy naphthoquinone toxicity in rats.
PubMed: Reduction and mutagenic activation of nitroaromatic compounds by a Mycobacterium sp.
PubMed: Evaluation of the antimutagenic potential of anthracene: in vitro and ex vivo studies.
PubMed: Differential toxicity of juglone (5-hydroxy-1,4-naphthoquinone) and related naphthoquinones to saturniid moths.
PubMed: The dose-dependent effect of BHT (butylated hydroxytoluene) on vitamin K-dependent blood coagulation in rats.
PubMed: Induction of the anti-carcinogenic enzyme quinone reductase by food extracts using murine hepatoma cells.
PubMed: Quantifying the vitamin K requirement of juvenile marine shrimp (Penaeus monodon) with menadione.
PubMed: S-thiolation and irreversible oxidation of sulfhydryls on carbonic anhydrase III during oxidative stress: a method for studying protein modification in intact cells and tissues.
PubMed: Selenium deficiency suppresses the S-glutathiolation of carbonic anhydrase III in rat hepatocytes under oxidative stress.
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PubMed: Dietary influences on rat hepatic and intestinal DT-diaphorase activity.
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