{{chembox | verifiedrevid = 412682209 | ImageFile=Moniliformin sodium.png | ImageSize=120px | IUPACName=Sodium 3,4-dioxo-1-cyclobuten-1-olate | OtherNames={{ubl|3-Hydroxycyclobut-3-ene-1,2-dione sodium salt|Moniliformin|Semisquaric acid sodium salt|Sodium semisquarate}} |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 36957 | InChI = 1/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H | InChIKey = KGPQKNJSZNXOPV-UHFFFAOYAJ | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = KGPQKNJSZNXOPV-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 31876-38-7 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = G5JMQ8SDF8 | PubChem = 40452 | SMILES = O=C1C(\O)=C/C1=O }} |Section2={{Chembox Properties | Formula={{chem2|NaC4HO3}} | C=4|H=1|Na=1|O=3 | Appearance=Yellow crystalline solid | Density= | MeltingPt=Decomposes at 345-355 °C without melting | Solubility=very good }} |Section7={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} |Section9={{Chembox Related | OtherCompounds=Squaric acid }} }}
'''Moniliformin''' is the organic compound with the formula {{chem2|M[C4HO3]}} (M<sup>+</sup> = K<sup>+</sup> or Na<sup>+</sup>). 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.<ref>{{cite journal |doi=10.1021/ja00814a055 |title=Structure and synthesis of moniliformin, a novel cyclobutane microbial toxin |date=1974 |last1=Springer |first1=James P. |last2=Clardy |first2=Jon |last3=Cole |first3=Richard J. |last4=Kirksey |first4=Jerry W. |last5=Hill |first5=Richard K. |last6=Carlson |first6=Robert M. |last7=Isidor |first7=John L. |journal=Journal of the American Chemical Society |volume=96 |issue=7 |pages=2267–2268 |pmid=4833647 }}</ref> 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.<ref>{{cite journal|title=A molecular mechanism for the toxic action of moniliformin, a mycotoxin produced by fusarium moniliforme|journal=Biochemical Pharmacology|volume=27|issue=4|pages=483–6|doi=10.1016/0006-2952(78)90381-7|pmid=629807|year=1978|last1=Thiel|first1=Pieter G}}</ref><ref>[https://fermentek.com/node/621 Moniliformin ] product page from Fermentek</ref><ref>[http://www.romerlabs.com/downloads/Mycotoxins/Moniliformin.pdf Moniliformin information leaflet] by Romerlab</ref> 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.{{cln|reason=What is "Ultrastructural examination"??? Please someone clarify this jargon!|date=August 2023}} Minks are considered most sensitive mammals to the toxicity of moniliformin.<ref>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</ref> 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.
λ<sub>max</sub>: 226 nm and 259 nm in methanol.
==See also== *Mycotoxin *Squaric acid
==Sources and references== {{reflist}}
Category:Mycotoxins Category:Organic sodium salts Category:Cyclobutenes Category:Respiratory toxins Category:Enols Category:Ketones Category:Organic acids