Semiquadratic acid

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Structural formula
Structure of semiquadratic acid
General
Surname Semiquadratic acid
other names
  • Moniliformin
  • 3-Hydroxycyclobut-3-en-1,2-dione ( IUPAC )
Molecular formula C 4 H 2 O 3
External identifiers / databases
CAS number
PubChem 40452
Wikidata Q904389
properties
Molar mass 98.06 g mol −1
Physical state

firmly

Melting point
  • 158 ° C
  • > 320 ° C (sodium and potassium salt)
pK s value

0.88

solubility

Decomposes in water and methanol

safety instructions
GHS hazard labeling
no classification available
Toxicological data

41 mg kg −1 ( LD 50ratoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Semiquadric acid , also called moniliformin , is, like the related squaric acid , a derivative of cyclobutene .

Occurrence

Moniliformin is a secondary metabolite from Fusarium moniliforme ( Gibberella fujikuroi ), Fusarium fusarioides and Fusarium sporotrichioides (fruit and corn molds). It occurs naturally as a potassium or sodium salt.

Chemical properties

The semi-square acid is the strongest naturally occurring organic acid ( pKa = 0.88), which consists only of carbon, hydrogen and oxygen.

After a proton has been split off, the anion of the semiquadric acid is mesomeric stabilized.

Physiological effect

Moniliformin is a mycotoxin and shows toxic and growth-regulating properties towards plants . The effect is based on a disruption of the pyruvate and α-ketoglutarate oxidation of the citric acid cycle in the mitochondria . A comprehensive compilation of the occurrence and toxic effects of moniliformin was prepared on behalf of the European Food Safety Authority EFSA.

Web links

Individual evidence

  1. a b c d e f Helle Katrine Knutsen, Jan Alexander, Lars Barregård, Margherita Bignami, Beat Brüschweiler, Sandra Ceccatelli, Bruce Cottrill, Michael Dinovi, Bettina Grasl ‐ Kraupp, Christer Hogstrand, Laurentius (Ron) Hoogenboom, Carlo Stefano Nebbia, Isabelle P. Oswald, Annette Petersen, Martin Rose, Alain-Claude Roudot, Tanja Schwerdtle, Christiane Vleminckx, Günter Vollmer, Heather Wallace, Sarah De Saeger, Gunnar Sundstøl Eriksen, Peter Farmer, Jean-Marc Fremy, Yun Yun Gong, Karsten Meyer , Hanspeter Naegeli, Dominique Parent ‐ Massin, Hans van Egmond, Andrea Altieri, Paolo Colombo, Mari Eskola, Mathijs van Manen, Lutz Edler: Risks to human and animal health related to the presence of moniliformin in food and feed . In: EFSA Journal . tape 16 , no. 3 , 2018, ISSN  1831-4732 , p. e05082 , doi : 10.2903 / j.efsa.2018.5082 .
  2. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. Entry on semiquadric acid in the ChemIDplus database of the United States National Library of Medicine (NLM)
  4. ^ Battilani P., Costa LG, Dossena A., Gullino ML, Marchelli R., Galaverna G., Pietri A., Dall'Asta C., Giorni P., Spadaro D., Gualla A .: Scientific information on mycotoxins and natural plant toxicants . In: EFSA Supporting Publications . tape 6 , no. 9 , December 2009, doi : 10.2903 / sp.efsa.2009.EN-24 (free full text).