Moniliformin
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| Names | |
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| IUPAC name
Sodium 3,4-dioxo-1-cyclobuten-1-olate
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| NaC4HO3 | |
| Molar mass | 120.039 g·mol−1 |
| Appearance | Yellow crystalline solid |
| Melting point | Decomposes at 345-355 °C without melting |
| very good | |
| Related compounds | |
Related compounds
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Squaric acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1] 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
[edit]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.[2][3][4] 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.[clarification needed] Minks are considered most sensitive mammals to the toxicity of moniliformin.[5] Chemically speaking, it is the sodium salt of deoxysquaric acid (the other name of that acid is semisquaric acid).
Physicochemical information
[edit]Moniliformin is soluble in water and polar solvents, such as methanol.
λmax: 226 nm and 259 nm in methanol.
See also
[edit]Sources and references
[edit]- ^ 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.
- ^ 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.
- ^ Moniliformin product page from Fermentek
- ^ Moniliformin information leaflet by Romerlab
- ^ 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