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Moniliformin

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Moniliformin
Names
IUPAC name Sodium 3,4-dioxo-1-cyclobuten-1-olate
Other names
  • 3-Hydroxycyclobut-3-ene-1,2-dione sodium salt
  • Moniliformin
  • Semisquaric acid sodium salt
  • Sodium semisquarate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5HKey: KGPQKNJSZNXOPV-UHFFFAOYSA-N
  • InChI=1/C4H2O3/c5-2-1-3(6)4(2)7/h1,5HKey: KGPQKNJSZNXOPV-UHFFFAOYAJ
SMILES
  • O=C1C(\O)=C/C1=O
Properties
Chemical formula NaC4HO3
Molar mass 120.039 g·mol
Appearance Yellow crystalline solid
Melting point Decomposes at 345-355 °C without melting
Solubility in water very good
Related compounds
Related compounds Squaric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Moniliformin is the organic compound with the formula M[C4HO3] (M = K or Na). Both the sodium and potassium salts are generally hydrated, e.g. . In terms of its structure, it is the alkali metal salt of the conjugate base of 3-hydroxy-1,2-cyclobutenedione (the enolate of 1,2,3-cyclobutanetrione), a planar molecule related to squaric acid. It is an unusual mycotoxin, a feed contaminant that is lethal to fowl, especially ducklings.

Moniliformin is formed in many cereals by a number of Fusarium species that include Fusarium moniliforme, Fusarium avenaceum, Fusarium subglutinans, Fusarium proliferatum, Fusarium fujikuroi and others. It is mainly cardiotoxic and causes ventricular hypertrophy.

Biochemistry

Moniliformin actually causes competitive inhibition of the activity of pyruvate dehydrogenase complex of respiratory reaction, which prevents pyruvic acid, product of glycolysis, to convert to acetyl-CoA. Ultrastructural examination of right ventricular wall of 9 month old female mink (Mustela vison) fed acute doses of moniliformin (2.2 and 2.8 mg/kg diet) and sub-acute doses (1.5 to 3.2 mg/kg diet) reveals significant damage to myofiber, mitochondria, Z and M lines and sarcoplasmic reticulum as well as increased extracellular collagen deposition. Minks are considered most sensitive mammals to the toxicity of moniliformin. Chemically speaking, it is the sodium salt of deoxysquaric acid (the other name of that acid is semisquaric acid).

Physicochemical information

Moniliformin is soluble in water and polar solvents, such as methanol.

λmax: 226 nm and 259 nm in methanol.

See also

Sources and references

  1. Springer, James P.; Clardy, Jon; Cole, Richard J.; Kirksey, Jerry W.; Hill, Richard K.; Carlson, Robert M.; Isidor, John L. (1974). "Structure and synthesis of moniliformin, a novel cyclobutane microbial toxin". Journal of the American Chemical Society. 96 (7): 2267–2268. doi:10.1021/ja00814a055. PMID 4833647.
  2. Thiel, Pieter G (1978). "A molecular mechanism for the toxic action of moniliformin, a mycotoxin produced by fusarium moniliforme". Biochemical Pharmacology. 27 (4): 483–6. doi:10.1016/0006-2952(78)90381-7. PMID 629807.
  3. Moniliformin product page from Fermentek
  4. Moniliformin information leaflet by Romerlab
  5. Morgan MK, Fitzgerald SD, Rottinghaus GE, Bursian SJ and Aulerich RJ. 1999. Toxic effects to mink of moniliformin extracted from Fusarium fujikuroi culture material. Veterinary and Human Toxicology 1(1):pp-1-5
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