Patulin

Patulin[1]
IUPAC name 4-hydroxy-4H-furo[3,2-c]pyran-2(6H)-one
Other names 2-Hydroxy-3,7-dioxabicyclo[4.3.0]nona-5,9-dien-8-one Clairformin Claviform Expansine Clavacin Clavatin Expansin Gigantin Leucopin Patuline
Identifiers
CAS number	149-29-1 Y
PubChem	4696
ChemSpider	4534 Y
UNII	95X2BV4W8R N
EC number	205-735-2
KEGG	C16748 N
ChEMBL	CHEMBL294018 Y
Jmol-3D images	Image 1
SMILES O=C\1O/C2=C/COC(O)C2=C/1
InChI InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2 Y Key: ZRWPUFFVAOMMNM-UHFFFAOYSA-N Y
Properties
Molecular formula	C7H6O4
Molar mass	154.12 g mol−1
Appearance	Compact prisms
Melting point	110 °C, 383 K, 230 °F
Solubility in water	Soluble
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[2] Patulin is also an antibiotic.^[1] Several countries have instituted patulin restrictions in apple products. The World Health Organization recommends a maximum concentration of 50 µg/L in apple juice.^[3]

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. ^[4]

References

1. ^ ^{a b} Merck Index, 11th Edition, 7002.
2. ^ "Patulin: a Mycotoxin in Apples". Perishables Handling Quarterly (91): 5. August 1997. http://ucce.ucdavis.edu/files/datastore/234-166.pdf. 
3. ^ "Foodborne hazards (World Health Organization". http://www.who.int/foodsafety/publications/capacity/en/2.pdf. Retrieved 2007-01-22. 
4. ^ Patulin information leaf from Fermentek