Menadione

Source: Wikipedia, the free encyclopedia.
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
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.000.338 Edit this at Wikidata
KEGG
UNII
  • 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
  • O=C\2c1c(cccc1)C(=O)/C(=C/2)C
Properties
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)
Insoluble
Pharmacology
B02BA02 (WHO)
  • Contraindicated (India)[2]
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  • Generally Rx or withdrawn for human use; approved in animal feed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):
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 ?)

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.

Biochemistry

Menadione is converted to

NQO1.[5]

Menadione is also a circulating form of vitamin K, produced in small amounts (1–5%) after intestinal absorption of K1 and K2. This circulation explains the uneven tissue distribution of MK-4, especially since menadione can penetrate the blood–brain barrier. The cleavage enzyme is yet to be identified. As K3 is known to be toxic in large amounts, researchers speculate that the cleavage process is closely regulated.[5]

Terminology

The compound is variously known as vitamin K3

GGCX in vitro)[8]
of the K vitamins.

Uses

The menadione core is apparent in the structure of vitamin K.

It is an intermediate in the chemical synthesis of vitamin K by first reduction to the diol menadiol, which is susceptible to coupling to the phytol.[9] It is a useful intermediate for organic synthesis in general, as it can be made and modified in a number of ways.[10]

Menadione can be used to generate

fastidious microorganisms.[11]

Animal feed

In the United States, menadione is used in various types of animal feed and is described as having a history of safe use for this purpose, being used in poultry feed prior to 1958.[12]

Low-dose menadione is used as an inexpensive micronutrient for livestock in many countries. Forms of menadione are also included in some pet foods in developed countries as a source of vitamin K. These doses have yielded no reported cases of toxicity from menadione in livestock or pets. Although handling may be hazardous, the European Food Safety Authority found in 2013 that it is an effective source of vitamin K in animal nutrition that does not pose a risk to the environment.[13]

Human use

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 in economically developed countries. Menadione for human use at pharmaceutical strength is available in some countries with large lower income populations, such as India.[2] The typical daily dose is 10 mg oral or 2 mg parenteral.[14] It is used in the treatment of hypoprothrombinemia outside of the United States.[2]

Toxicology

Menadione is not believed to be carcinogenic.

redox cycling and arylation of thiols using its reactive 3-position.[5] ROS generation explains various toxic effects of excessive menadione, including DNA damage and cell death,[15] or on a whole-animal level, cardiac and renal toxicity in rats.[16]

References

  1. The Merck Index
    , 11th Edition, 5714
  2. ^ a b c "Menadione drug information". DrugsUpdate India.
  3. ^
    PMID 24085302
    .
  4. PMID 19098979
    .
  5. ^
    PMID 24489112
    .
  6. S2CID 19076885
    .
  7. ^ "Vitamin K". Linus Pauling Institute. 2014-04-22. Retrieved 2021-01-28.
  8. PMID 2112953
    .
  9. S2CID 86263542
    .
  10. PMID 35529893
    .
  11. ^ "Menadione". Sigma-Aldrich. Retrieved 2 February 2023.
  12. ^ "Vitamin K Substances and Animal Feed". FDA. 2 April 2021.
  13. doi:10.2903/j.efsa.2014.3532
    .
  14. ^ "Menadione (B02BA02)". WHOCC - ATC/DDD Index.
  15. ^
    S2CID 242264898
    .
  16. PMID 9482121
    .

External links

  • Menadione in the Pesticide Properties DataBase (PPDB)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Menadione&oldid=1210401376"