Moniliformin

Moniliformin
Names
	IUPAC name 3-hydroxycyclobut-3-ene-1,2-dione
	Other names Semisquaric acid
Identifiers
CAS Number	31876-38-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	36957 ;
PubChem CID	40452;
UNII	G5JMQ8SDF8 ;
CompTox Dashboard (EPA)	DTXSID10185731 ;
	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	very good
Related compounds
Related compounds	Squaric acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	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]^[3] 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.^[4] Chemically speaking, it is the sodium salt of deoxysquaric acid

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[]

^ 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
^ 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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[1] 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.

[2] Moniliformin product page from Fermentek

[3] Moniliformin information leaflet by

[4] 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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Moniliformin

Physicochemical information[]

See also[]

Sources and references[]