208:
24:
372:
637:
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".
385:
257:
540:) 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
593:
423:(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
673:
Thiel, Pieter G (1978). "A molecular mechanism for the toxic action of moniliformin, a mycotoxin produced by fusarium moniliforme".
222:
737:
Morgan MK, Fitzgerald SD, Rottinghaus GE, Bursian SJ and
Aulerich RJ. 1999. Toxic effects to mink of moniliformin extracted from
511:
766:
392:
563:
deposition. Minks are considered most sensitive mammals to the toxicity of moniliformin. Chemically speaking, it is the
165:
776:
186:
109:
495:
791:
553:
507:
771:
480:
474:
36:
462:
428:
203:
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75:
722:
486:
468:
726:
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527:
786:
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647:
408:
333:
280:
174:
129:
85:
207:
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Except where otherwise noted, data are given for materials in their
568:
108:
98:
707:
531:
440:
424:
191:
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574:(the other name of that acid is semisquaric acid).
153:
84:
51:3-Hydroxycyclobut-3-ene-1,2-dione sodium salt
8:
206:
128:
15:
327:Decomposes at 345-355 °C without melting
173:
640:Journal of the American Chemical Society
514:of respiratory reaction, which prevents
418:
414:
292:
288:
629:
526:. Ultrastructural examination of right
439:, a feed contaminant that is lethal to
262:
227:
202:
231:InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H
582:Moniliformin is soluble in water and
241:InChI=1/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H
234:Key: KGPQKNJSZNXOPV-UHFFFAOYSA-N
40:Sodium 3,4-dioxo-1-cyclobuten-1-olate
7:
427:of the conjugate base of 3-hydroxy-
244:Key: KGPQKNJSZNXOPV-UHFFFAOYAJ
144:
14:
723:Moniliformin information leaflet
370:
22:
743:Veterinary and Human Toxicology
450:Moniliformin is formed in many
431:, a planar molecule related to
366:(at 25 °C , 100 kPa).
512:pyruvate dehydrogenase complex
1:
506:Moniliformin actually causes
687:10.1016/0006-2952(78)90381-7
57:Semisquaric acid sodium salt
578:Physicochemical information
808:
490:and others. It is mainly
360:
343:
317:Yellow crystalline solid
273:
253:
218:
68:
45:
35:
30:
21:
675:Biochemical Pharmacology
603:and 259 nm in methanol.
496:ventricular hypertrophy
624:Sources and references
554:sarcoplasmic reticulum
530:of 9 month old female
508:competitive inhibition
556:as well as increased
481:Fusarium proliferatum
475:Fusarium subglutinans
460:species that include
767:Organic sodium salts
463:Fusarium moniliforme
429:1,2-cyclobutanedione
652:10.1021/ja00814a055
510:of the activity of
435:. It is an unusual
334:Solubility in water
309: g·mol
60:Sodium semisquarate
18:
777:Respiratory toxins
741:culture material.
739:Fusarium fujikuroi
710:product page from
487:Fusarium fujikuroi
469:Fusarium avenaceum
393:Infobox references
344:Related compounds
16:
411:with the formula
401:Chemical compound
399:
398:
350:Related compounds
187:CompTox Dashboard
110:Interactive image
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646:(7): 2267–2268.
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528:ventricular wall
522:, to convert to
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409:organic compound
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377:
374:
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295:
281:Chemical formula
265:O=C1C(\O)=C/C1=O
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584:polar solvents
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792:Organic acids
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708:Moniliformin
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558:extracellular
555:
551:
550:Z and M lines
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537:Mustela vison
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518:, product of
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443:, especially
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324:
323:Melting point
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17:Moniliformin
772:Cyclobutenes
742:
738:
733:
718:
703:
681:(4): 483–6.
678:
674:
668:
643:
639:
632:
618:Squaric acid
592:
581:
572:squaric acid
546:mitochondria
535:
516:pyruvic acid
505:
502:Biochemistry
485:
479:
473:
467:
461:
455:
449:
433:squaric acid
405:Moniliformin
404:
403:
355:Squaric acid
69:Identifiers
54:Moniliformin
46:Other names
745:1(1):pp-1-5
565:sodium salt
494:and causes
492:cardiotoxic
314:Appearance
274:Properties
762:Mycotoxins
756:Categories
586:, such as
524:acetyl-CoA
520:glycolysis
339:very good
302:Molar mass
175:G5JMQ8SDF8
121:ChemSpider
97:3D model (
86:31876-38-7
76:CAS Number
37:IUPAC name
712:Fermentek
613:Mycotoxin
445:ducklings
437:mycotoxin
727:Romerlab
607:See also
588:methanol
561:collagen
542:myofiber
457:Fusarium
787:Ketones
660:4833647
452:cereals
413:M[C
407:is the
386:what is
384: (
307:120.039
296:
142:PubChem
695:629807
693:
658:
599:: 226
381:verify
378:
258:SMILES
31:Names
782:Enols
569:deoxy
223:InChI
155:40452
130:36957
99:JSmol
691:PMID
656:PMID
552:and
532:mink
441:fowl
425:salt
166:UNII
725:by
683:doi
648:doi
596:max
567:of
498:.
287:NaC
192:EPA
145:CID
758::
689:.
679:27
677:.
654:.
644:96
642:.
601:nm
590:.
548:,
544:,
484:,
478:,
472:,
466:,
447:.
417:HO
291:HO
697:.
685::
662:.
650::
594:λ
534:(
421:]
419:3
415:4
376:Y
293:3
289:4
194:)
190:(
101:)
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