3714 Patulin Patulin is found in pomes. Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice Patulin is a mycotoxin produced by a variety of molds, particularly 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 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 ug/L in apple juice. Patulin has been shown to exhibit apoptotic and antibiotic functions (A7849, A7850). Patulin belongs to the family of Pyrans. These are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. 149-29-1 4696 C7H6O4 Compact prisms. 111°C Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Patulin's strong affinity to sulfhydryl groups enables to to inhibit a number of enzymes, including succinate dehydrogenase, alcohol dehydrogenases, ATPases, acetylcholinesterase, aldolases, protein tyrosine phosphatases, RNA polymerases, aminoacyl-tRNA synthetase, ribonuclease H, and lactate dehydrogenase. This widespread enzyme inhibition has a number of effects, including inhibition of aerobic respiration, inhibition of RNA synthesis, and inhibition of protein synthesis. Patulin also affects some aspects of membrane permeability and causes DNA-strand breakage and chromosomal aberrations, likely contributing to it's genotoxicity. Patulin may also cause the development of allergies by inhibiting interferon-gamma production. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (L1943, A2952, A3014) Metabolism of patulin is limited. No metabolic products have been identified. It is quite likely that the metabolic fragments or conjugated metabolites of patulin either are bound to the cell membrane or become incorporated into the cellular components. (L1943) LD50: 29-48 mg/kg (Oral, Mouse) (L1944) LD50: 10 mg/kg (Subcutaneous, Mosue) (L1944) LD50: 5.7-8.17 mg/kg (Intraperitoneal, Mouse) (L1944) LD50: 8.57 mg/kg (Intravenous, Mouse) (L1944) 3, not classifiable as to its carcinogenicity to humans. (L135) Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. Although patulin can occur in many molding fruits, grains and other foods, the major source of patulin contamination is in apples with brown rot, and in apple cider or apple juice. Patulin is also an antibiotic. (L1942, L1943) The World Health Organization recommends a maximum concentration of 50 µg/kg (50 ppb) in juices. (L1944) Animals studies have shown patulin to cause gastrointestinal hyperemia, distension, hemorrhage and ulceration. It has also been shown to be immunotoxic, and neurotoxic. (L1944, L1945) Skin irritation occurs in cases of topical exposure. Patulin is also a stomach irritant and causes nausea and vomiting if ingested. (L1945) Symptomatic and supportive care is the mainstay of therapy. (A704) 2009-12-17T22:12:11Z 2026-05-14T19:52:01Z http://en.wikipedia.org/wiki/Patulin C16748 DB15586 true OC1OCC=C2OC(=O)C=C12 C7H6O4 InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2 ZRWPUFFVAOMMNM-UHFFFAOYSA-N 154.1201 154.02660868 Exogenous Solid -0.38 HMDB34299 4534 CHEM002630 DTXSID2021101 NS00011821 4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one 55.760000000000005 37.034800000000004 13.76783675647027 0 3 1 11.653255322696081 -4.262666098015411 0 2 -0.27 0.02 1.63e+02 g/l