Patulin
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| Names | |||
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IUPAC name
4-hydroxy-4H-furo[3,2-c]pyran-2(6H)-one
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| 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 |
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| Identifiers | |||
149-29-1 
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| 3D model (Jmol) | Interactive image | ||
| ChEBI |
CHEBI:74926 
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| ChEMBL |
ChEMBL294018
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| ChemSpider |
4534
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| ECHA InfoCard | 100.005.215 | ||
| EC Number | 205-735-2 | ||
| KEGG |
C16748
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| PubChem | 4696 | ||
| UNII |
95X2BV4W8R
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| Properties | |||
| C7H6O4 | |||
| Molar mass | 154.12 g/mol | ||
| Appearance | Compact prisms | ||
| Density | 1.52 g/ml | ||
| Melting point | 110 °C (230 °F; 383 K) | ||
| Soluble | |||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is ?) |
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| Infobox references | |||
Patulin is a mycotoxin produced by a variety of molds, in particular, Aspergillus and Penicillium and Byssochlamys. Most commonly found in rotting apples, in general the amount of patulin in apple products is viewed as a measure of the quality of the apples used in production. In addition, patulin has been found in other foods such as grains, fruits, and vegetables. While not considered a particularly potent toxin, a number of studies have shown patulin to be genotoxic, which has led some to theorize that it may be a carcinogen, although animal studies have remained inconclusive. Patulin has shown antimicrobial properties against some microorganisms. 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 the 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.
Patulin is a white powder soluble in low-pH water and organic solvents. It is a polyketide lactone that is heat-stable, so it is not destroyed by pasteurization or thermal denaturation. However, stability following fermentation is lessened. Isoepoxydon dehydrogenase (IDH) is an important enzyme in the multi-step biosynthesis of patulin, and its gene is present in other fungi that may potentially produce the toxin. It is reactive with sulfur dioxide, so antioxidant and antimicrobial agents may be useful to destroy it. Levels of nitrogen, manganese, and pH as well as abundance of necessary enzymes regulate the biosynthetic pathway of patulin.
Patulin was originally used as an antibiotic against Gram-positive and Gram-negative bacteria, but after several toxicity reports, it is no longer used for that purpose. It was specifically trialed to be used against the common cold. Patulin is used as a potassium-uptake inhibitor in laboratory applications. Kashif Jilani and co-workers reported that patulin stimulates suicidal erythrocyte death under physiological concentrations.
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