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M5269

Sigma-Aldrich

Moniliformin sodium salt from Fusarium proliferatum

Synonym(s):

1-Hydroxycyclobut-1-ene-3,4-dione

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About This Item

Linear Formula:
C4HO3Na
CAS Number:
71376-34-6
Molecular Weight:
120.04
MDL number:
MFCD00056566
UNSPSC Code:
12352200
PubChem Substance ID:
24896991
NACRES:
NA.77

$308.00

Available to ship onApril 10, 2025Details

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Quality Level

200

storage temp.

2-8°C

SMILES string

O=C1C(C=C1[O-])=O.[Na+]

InChI

1S/C4H2O3.Na/c5-2-1-3(6)4(2)7;/h1,5H;/q;+1/p-1

InChI key

FERDNJVXTWPNSA-UHFFFAOYSA-M

General description

Moniliformin (MON), a mycotoxin[1] and small ionic molecule[2], is present in various Fusarium species including Fusarium avenaceum, Fusarium subglutinans and Fusarium proliferatum.[1] It is present as sodium or potassium salt of semisquaric acid naturally.[1] MON is also present in maize and small-grain cereals.[2]

Application

Moniliformin sodium salt from Fusarium proliferatum has been used as a mycotoxin standard:
  • to test its acute oral toxicity in mice[1]
  • to test its subacute toxic effects in rats[2]
  • in characterizing mycotoxins from Aspergillus[3]

Biochem/physiol Actions

Moniliformin (MON) is implicated for its toxic potential and may lead to respiratory distress and progressive muscular weakness in rats.[1] It inhibits the tricarboxylic acid (TCA) cycle oxidation step.[1] By acting as a pyruvate substrate, MON effectively inhibits thiamine pyrophosphate cofactor dependant enzymes and blocks the gluconeogenesis pathway.[1] ) Furthermore, MON also inhibits glutathione peroxidase and glutathione reductase leading to oxidative stress in myoblast.[2]

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000406511
0000406511
0000362506
0000362506
0000138000

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H R Burmeister et al.
Applied and environmental microbiology, 37(1), 11-13 (1979-01-01)
Fusarium moniliforme NRRL 6322 produced about 600 mg of recoverable moniliformin, a mycotoxic metabolite, per kg of corn grit medium. The moniliformin was extracted from the grits with methanol, purified by preparative thin-layer chromatography, and crystallized from ether. The 50%
Fusarium species colonizing spears and forming mycotoxins in field samples of asparagus from Germany and Poland
Weber Z, et al.
Journal of Phytopathology, 209-216 null
Martina Jonsson et al.
Toxicology letters, 233(1), 38-44 (2014-12-09)
Moniliformin is a Fusarium mycotoxin mainly produced by several species infecting grains in different climatic conditions. According to our previous studies, it is acutely toxic to rats, with an LD50 cut-off value of 25mg/kg b.w. To further assess the possible
An Zhang et al.
Journal of Zhejiang University. Science. B, 11(3), 200-208 (2010-03-06)
To investigate the effects of mycotoxin moniliformin (MON) on the metabolism of aggrecan and type II collagen in human chondrocytes in vitro and the relationship between MON and Kashin-Beck disease (KBD). Human chondrocytes were isolated and cultured on bone matrix
D Sharma et al.
Poultry science, 87(6), 1039-1051 (2008-05-22)
A total of 390 one-day-old quail chicks (Coturnix coturnix japonica) were divided into 4 groups (3 replicates per treatment), viz. CX, FX, MX, and FM, containing 75, 105, 105, and 105 birds, respectively. Birds in the control group (CX) were
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