Moniliformin

Moniliformin

Names
IUPAC name sodium 3,4-dioxo-1-cyclobutenolate
Identifiers
CAS Number	71376-34-6
3D model (Jmol)	Interactive image
ChemSpider	36957
PubChem	40452
InChI InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H Key: KGPQKNJSZNXOPV-UHFFFAOYSA-N InChI=1/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H Key: KGPQKNJSZNXOPV-UHFFFAOYAJ
SMILES O=C1C(\O)=C/C1=O
Properties
Chemical formula	C4HNaO3
Molar mass	120.04 g/mol
Appearance	Yellow crystalline solid
Melting point	Decomposes at 345-355 °C without melting
Solubility in water	yes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Moniliformin 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. 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.^[1][2] 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. Mink is considered most sensitive mammals to the toxicity of moniliformin.^[3]

Physicochemical information

IUPAC name: 3-hydroxy-3-cyclobutene-1,2-dione. Solubility information: Moniliformin is soluble in water and polar solvents, such as methanol.
λmax: 226, 259 in methanol

Sources and references

1. Moniliformin product page from Fermentek
2. Moniliformin information leaflet by Romerlab
3. 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