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Patulin

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Patulin
Names
IUPAC name 4-hydroxy-4H-furopyran-2(6H)-one
Other names 2-Hydroxy-3,7-dioxabicyclonona-5,9-dien-8-one
Clairformin
Claviform
Expansine
Clavacin
Clavatin
Expansin
Gigantin
Leucopin
Patuline
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.215 Edit this at Wikidata
EC Number
  • 205-735-2
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2Key: ZRWPUFFVAOMMNM-UHFFFAOYSA-N
  • Key: ZRWPUFFVAOMMNM-UHFFFAOYAU
SMILES
  • O=C\1O/C2=C/COC(O)C2=C/1
Properties
Chemical formula C7H6O4
Molar mass 154.12 g/mol
Appearance Compact prisms
Melting point 110 °C (230 °F; 383 K)
Solubility in water Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Patulin is a mycotoxin produced by a variety of molds, in particular, Aspergillus and Penicillium. It is commonly found in rotting apples, and the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. It is not a particularly potent toxin, but a number of studies have shown that it is genotoxic, which has led to some theories that claim that it may be a carcinogen, though animal studies have remained inconclusive. Patulin is also an antibiotic. Several countries have instituted patulin restrictions in apple products. The World Health Organization recommends a maximum concentration of 50 µg/L in apple juice.

In European Union, the limit is set to 50 micrograms per kilogram (µg/kg) in both apple juice and cider, and to half of that concentration, 25 µg/kg in solid apple products and 10 µg/kg in products for infants and young children. These limits came into force on 1 November 2003.

References

  1. ^ Merck Index, 11th Edition, 7002.
  2. "Patulin: a Mycotoxin in Apples" (PDF). Perishables Handling Quarterly (91): 5. August 1997.
  3. "Foodborne hazards (World Health Organization" (PDF). Retrieved 2007-01-22.
  4. Patulin information leaf from Fermentek
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