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Menadione information


Not to confuse with menaquinone-3, aka MK-3, a version of vitamin K2 series having 3 isoprene groups
Menadione[1]
Skeltal formula
Ball-and-stick model
Names
Preferred IUPAC name
2-Methylnaphthalene-1,4-dione
Other names
Menaphthone; Vitamin K3; β-Methyl-1,4-naphthoquinone; 2-Methyl-1,4-naphthodione; 2-Methyl-1,4-naphthoquinone
Identifiers
CAS Number
  • 58-27-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28869 ☒N
ChEMBL
  • ChEMBL590 checkY
ChemSpider
  • 3915 checkY
DrugBank
  • DB00170 ☒N
ECHA InfoCard 100.000.338 Edit this at Wikidata
KEGG
  • D02335 checkY
PubChem CID
  • 4055
UNII
  • 723JX6CXY5 checkY
CompTox Dashboard (EPA)
  • DTXSID4021715 Edit this at Wikidata
InChI
  • InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 checkY
    Key: MJVAVZPDRWSRRC-UHFFFAOYSA-N checkY
  • InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
    Key: MJVAVZPDRWSRRC-UHFFFAOYAY
SMILES
  • O=C\2c1c(cccc1)C(=O)/C(=C/2)C
Properties
Chemical formula
 C11H8O2
Molar mass 172.183 g·mol−1
Appearance Bright yellow crystals
Density 1.225g/cm3
Melting point 105 to 107 °C (221 to 225 °F; 378 to 380 K)
Solubility in water
 Insoluble
Pharmacology
ATC code
 B02BA02 (WHO)
Pregnancy
category
  • Contraindicated (India)[2]
Routes of
administration
  • Oral
  • Intravenous
  • Intramuscular
Legal status
  • Generally Rx or withdrawn for human use; approved in animal feed
Hazards
Flash point 113.8 °C (236.8 °F; 386.9 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 0.5 g/kg (oral, mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Menadione is a natural[3] organic compound with the formula C6H4(CO)2C2H(CH3). It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position.[4] It is sometimes called vitamin K3. Use is allowed as a nutritional supplement in animal feed because of its vitamin K activity.

  1. ^ The Merck Index, 11th Edition, 5714
  2. ^ Cite error: The named reference dui was invoked but never defined (see the help page).
  3. ^ Hirota, Yoshihisa; Tsugawa, Naoko; Nakagawa, Kimie; Suhara, Yoshitomo; Tanaka, Kiyoshi; Uchino, Yuri; Takeuchi, Atsuko; Sawada, Natsumi; Kamao, Maya; Wada, Akimori; Okitsu, Takashi (2013-11-15). "Menadione (vitamin K3) is a catabolic product of oral phylloquinone (vitamin K1) in the intestine and a circulating precursor of tissue menaquinone-4 (vitamin K2) in rats". The Journal of Biological Chemistry. 288 (46): 33071–33080. doi:10.1074/jbc.M113.477356. ISSN 1083-351X. PMC 3829156. PMID 24085302.
  4. ^ Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD (2008). Fox (ed.). "Cytotoxicity mechanism of two naphthoquinones (menadione and plumbagin) in Saccharomyces cerevisiae". PLOS ONE. 3 (12): e3999. Bibcode:2008PLoSO...3.3999C. doi:10.1371/journal.pone.0003999. PMC 2600608. PMID 19098979.

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Menadione

Last Update:

Menadione is a natural organic compound with the formula C6H4(CO)2C2H(CH3). It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position...

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Vitamin K

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by bacteria, which use these during anaerobic respiration. Vitamin K3 (menadione), a synthetic form of vitamin K, was used to treat vitamin K deficiency...

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Provitamin

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which may be converted in the body to vitamin B5 (pantothenic acid). Menadione is a synthetic provitamin of vitamin K. Provitamin D2 is ergosterol, and...

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Autoschizis

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and light microscopy of a new cell death induced by sodium ascorbate: Menadione treatment". Scanning. 25 (3): 137–49. doi:10.1002/sca.4950250306. PMID 12866647...

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Naphthoquinone

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Spinochrome D Vitamin K and related compounds Phylloquinone Vitamin K2 Menadione (2-Methyl-1,4-naphthoquinone) 5,8-Dihydroxy-1,4-naphthoquinone and...

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List of micronutrients

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Vitamin K Vitamin K1 (phylloquinone) Vitamin K2 (menaquinone) Vitamin K3 (menadione) Carotenoids (not accepted as essential nutrients) Alpha carotene Beta...

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Menadiol

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after surgery). Menadiol is probably naturally produced by reduction of menadione ("vitamin K3"; see Quinone § Reduction) as an intermediate in the conversion...

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MNB

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name of the central bank of Hungary Menadione Nicotinamide Bisulfite, a synthetic chemical compound – see Menadione This disambiguation page lists articles...

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Vitamin

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(tocopherols and tocotrienols) Vitamin K (phylloquinones, menaquinones, and menadiones) Some sources include a fourteenth, choline. Vitamins have diverse biochemical...

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Vitamin K2

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of vitamin K, the other two being vitamin K1 (phylloquinone) and K3 (menadione). K2 is both a tissue and bacterial product (derived from vitamin K1 in...

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Glossary of chemical formulae

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87120-72-7 C10H20O2 Paramenthane hydroperoxide C10H22 decane 124-18-5 C11H8O2 menadione 58-27-5 C11H10O β-Naphthol methyl ether 93-04-9 C11H11NO2 3-indolepropionic...

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C11H8O2

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exact mass: 172.0524 u) may refer to: 1-Naphthoic acid 2-Naphthoic acid Menadione This set index page lists chemical structure articles associated with...

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K3

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(programming language) K3 surface, a compact complex surface in mathematics Menadione, vitamin K3 K3, 1774 marine chronometer made by Larcum Kendall Pentax...

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Food fortification

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is toxic in a much lower dose than other forms, such as beta carotene. Menadione, a phased-out synthetic form of Vitamin K, is also known to be toxic.[medical...

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NADH dehydrogenase

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diaphorase, NADH diaphorase, NADH hydrogenase, NADH oxidoreductase, NADH-menadione oxidoreductase, reduced diphosphopyridine nucleotide diaphorase Databases...

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Competitive inhibition

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including methylene blue, 5-nitroindazole, norharman, 9-methylnorharman, and menadione. These demonstrated a reduction of neurotoxicity produced by MPTP. Sulfa...

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Menatetrenone

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three steps: Removal of the phytyl tail to form menadione (K3; unknown enzyme); Reduction of menadione to menadiol (likely NQO1); Attachment of GGPP tail...

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Plumbagin

Last Update:

H. (2010). "Terahertz and Infrared Spectra of Plumbagin, Juglone, and Menadione". Carnivorous Plant Newsletter. 39 (3): 82–88. Rischer, H.; Hamm, A.;...

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ATC code B02

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antitrypsin B02AB04 Camostat B02AB05 Ulinastatin B02BA01 Phytomenadione B02BA02 Menadione B02BB01 Human fibrinogen B02BC01 Absorbable gelatin sponge B02BC02 Oxidized...

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Vitamer

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d-gamma, and d-delta-tocopherol), tocotrienols (alpha, beta, gamma, delta tocotrienols) Vitamin K phylloquinone(K1), menaquinones (K2), menadiones (K3)...

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Electrovite

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acid (B9), ascorbic acid (vitamin C), along with a vitamin K derivative, menadione sodium bisulfite DVL adds these vitamins to an electrolyte premix that...

Word Count : 441

Glutathione reductase

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of human Glutathione Reductase complexed with a Fluoro-Analogue of the Menadione Derivative M5 2grt: HUMAN GLUTATHIONE REDUCTASE A34E, R37W MUTANT, OXIDIZED...

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Redox therapy

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administering high dosages of vitamins; in a 1984 study, high dosages of Menadione and Vitamin C were given to a patient. Antioxidant therapy Orthomolecular...

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