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P1639 Sigma

Patulin

≥98% (TLC)

Synonym: 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics N-S, Biochemicals and Reagents
Quality Level   PREMIUM
assay   ≥98% (TLC)
solubility   ethyl acetate: soluble50 mg/mL
antibiotic activity spectrum   molds
storage temp.   −20°C

Description

Application

Patulin is a mycotoxin produced by a variety of molds, such as, Aspergillus and Penicillium. It is commonly found in apples. It is used as an inhibitor of potassium uptake and as an inducer of ion flux across cell membranes, potentially involving Na+-K+ dependent ATPase and to induce intra- and intermolecular protein crosslinking. It is used to study patulin contamination of bottled wine1, DNA-damaging activity of patulin in Escherichia coli2, and molecular cloning and functional characterization of two CYP619 cytochrome P450s involved in biosynthesis of patulin in Aspergillus clavatus3.

Biochem/physiol Actions

Patulin is genotoxic and may be carcinogenic.

Price and Availability

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Patulin solution

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
Safety Statements (Europe) 
45
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
3
RTECS 
LV2625000

Protocols & Articles

Peer-Reviewed Papers

References

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1. Birkinshaw, M., et al. Lancet 245, 625, (1943)

2. Effects of various lactones and related compounds on cation transfer in incubated cold-stored human erythrocytes. Kahn J. Pharmacol. Exp. Ther. 121, 234, (1957)

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Low Occurrence of Patulin-Producing Strains of Penicillium in Grapes and Patulin Degradation during Winemaking in Chile Gonzalo A. Díaz, Lina Yañez, et al. Am. J. Enol. Vitic. 62, 542-546, (2011)

DNA-damaging activity of patulin in Escherichia coli. K S Lee and R J Röschenthaler Appl. Environ. Microbiol. 52, 1046-1054, (1986)

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Molecular cloning and functional characterization of two CYP619 cytochrome P450s involved in biosynthesis of patulin in Aspergillus clavatus Marie Pierre Artigot, Nicolas Loiseau, et al. Microbiology 155, 1738-1747, (2009)

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Identifying off-target effects and hidden phenotypes of drugs in human cells. Marnie L MacDonald et al Nat. Chem. Biol. 2, 329-37, (2006)

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In vivo fluorescence imaging of bacteriogenic cyanide in the lungs of live mice infected with cystic fibrosis pathogens. Nam SW, Chen X, Lim J, et al. PLoS ONE 6(7), e21387, (2011)

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Minigenome-based reporter system suitable for high-throughput screening of compounds able to inhibit Ebolavirus replication and/or transcription. Luke D Jasenosky et al Antimicrob. Agents Chemother. 54, 3007-10, (2010)

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Evaluation of nephrotoxic effects of mycotoxins, citrinin and patulin, on zebrafish (Danio rerio) embryos. Wu TS, Yang JJ, Yu FY, et al. Food Chem. Toxicol. 50(12), 4398-404, (2012)

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Control of hepatitis C: a medicinal chemistry perspective. Christopher P Gordon et al J. Med. Chem. 48, 1-20, (2005)

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Improved positive electrospray ionization of patulin by adduct formation: usefulness in liquid chromatography-tandem mass spectrometry multi-mycotoxin analysis. Malysheva SV, Diana Di Mavungu J, Boonen J, et al. J. Chromatogr. A 1270, 334-9, (2012)

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Patulin reduction in apple juice by inactivated Alicyclobacillus spp. Yuan Y, Wang X, Hatab S, et al. Lett. Appl. Microbiol. 59(6), 604-9, (2014)

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Determination of patulin in apple and derived products by UHPLC-MS/MS. Study of matrix effects with atmospheric pressure ionisation sources. Beltrán E, Ibáñez M, Sancho JV, et al. Food Chem. 142, 400-7, (2014)

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EGFR-mediated Akt and MAPKs signal pathways play a crucial role in patulin-induced cell proliferation in primary murine keratinocytes via modulation of Cyclin D1 and COX-2 expression. Alam S, Pal A, Kumar R, et al. Mol. Carcinog. 53(12), 988-98, (2014)

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Progress in the chemistry of organic natural products. The chemistry of mycotoxins. Bräse S, Gläser F, Kramer CS, et al. Fortschr. Chem. Org. Naturst. 97, v-xv, 1-300, (2013)

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[Determination of patulin in juice by ultra performance liquid chromatography-tandem mass spectrometry]. Niu H, Feng L, Niu Z, et al. Se Pu 30(9), 957-61, (2012)

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[Patulin]. Criseo G, Guerrisi R, and Forestieri F Ann. Ig. 2(5), 343-52, (1990)

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Patulin and secondary metabolite production by marine-derived Penicillium strains. Vansteelandt M, Kerzaon I, Blanchet E, et al. Fungal Biol. 116(9), 954-61, (2012)

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High-content single-cell drug screening with phosphospecific flow cytometry. Peter O Krutzik et al Nat. Chem. Biol. 4, 132-42, (2008)

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Development of a multiplex real-time PCR to quantify aflatoxin, ochratoxin A and patulin producing molds in foods. Rodríguez A, Rodríguez M, Andrade MJ, et al. Int. J. Food Microbiol. 155(1-2), 10-8, (2012)

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Chromatographic determination of the mycotoxin patulin in fruit and fruit juices. Shephard GS and Leggott NL J. Chromatogr. A 882(1-2), 17-22, (2000)

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The mycotoxin patulin increases colonic epithelial permeability in vitro. Mohan HM, Collins D, Maher S, et al. Food Chem. Toxicol. 50(11), 4097-102, (2012)

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Patulin: Mechanism of genotoxicity. Glaser N and Stopper H Food Chem. Toxicol. 50(5), 1796-801, (2012)

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Biosynthesis and toxicological effects of patulin. Puel O, Galtier P, and Oswald IP Toxins (Basel.) 2(4), 613-31, (2010)

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Regulation of patulin-induced oxidative stress processes in the fission yeast Schizosaccharomyces pombe. Papp G, Horváth E, Mike N, et al. Food Chem. Toxicol. 50(10), 3792-8, (2012)

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Hplc detection of patulin in apple juice with GC/MS confirmation of patulin identity. Roach JA, Brause AR, Eisele TA, et al. Adv. Exp. Med. Biol. 504, 135-40, (2002)

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Simultaneous determination of bisphenol A, aflatoxin B1, ochratoxin A, and patulin in food matrices by liquid chromatography/mass spectrometry. Song W, Li C, and Moezzi B Rapid Commun. Mass Spectrom. 27(6), 671-80, (2013)

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A novel method for determination of patulin in apple juices by GC-MS. Kharandi N, Babri M, and Azad J Food Chem. 141(3), 1619-23, (2013)

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Molecular characterization, fitness and mycotoxin production of benzimidazole-resistant isolates of Penicillium expansum. Malandrakis AA, Markoglou AN, Konstantinou S, et al. Int. J. Food Microbiol. 162(3), 237-44, (2013)

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Patulin reduction in apple juice from concentrate by UV radiation and comparison of kinetic degradation models between apple juice and apple cider. Assatarakul K, Churey JJ, Manns DC, et al. J. Food Prot. 75(4), 717-24, (2012)

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Ability of inactivated yeast powder to adsorb patulin from apple juice. Guo C, Yue T, Hatab S, et al. J. Food Prot. 75(3), 585-90, (2012)

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Study of thermal resistance and in vitro bioaccessibility of patulin from artificially contaminated apple products. Raiola A, Meca G, García-Llatas G, et al. Food Chem. Toxicol. 50(9), 3068-72, (2012)

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Removal of patulin from apple juice using inactivated lactic acid bacteria. Hatab S, Yue T, and Mohamad O J. Appl. Microbiol. 112(5), 892-9, (2012)

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A new solid-phase extraction and HPLC method for determination of patulin in apple products and hawthorn juice in China. Zhou Y, Kong W, Li Y, et al. J. Sep. Sci. 35(5-6), 641-9, (2012)

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A sensitive gas chromatography-mass spectrometry method for the determination of patulin in apple juice. Xiao H and Fu S J. AOAC Int. 95(6), 1709-12, (2012)

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Sequencing, physical organization and kinetic expression of the patulin biosynthetic gene cluster from Penicillium expansum. Tannous J, El Khoury R, Snini SP, et al. Int. J. Food Microbiol. 189, 51-60, (2014)

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Individual and combined effects of mycotoxins from typical indoor moulds. Mueller A, Schlink U, Wichmann G, et al. Toxicol. In Vitro 27(6), 1970-8, (2013)

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Patulin induces pro-survival functions via autophagy inhibition and p62 accumulation. Guo X, Dong Y, Yin S, et al. Cell Death Dis. 4, e822, (2013)

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Effects of aliphatic aldehydes on the growth and patulin production of Penicillium expansum in apple juice. Taguchi T, Kozutsumi D, Nakamura R, et al. Biosci. Biotechnol. Biochem. 77(1), 138-44, (2013)

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Reduction of patulin in aqueous solution by lactic acid bacteria. Hatab S, Yue T, and Mohamad O J. Food Sci. 77(4), M238-41, (2012)

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Kinetics of patulin degradation in model solution, apple cider and apple juice by ultraviolet radiation. Zhu Y, Koutchma T, Warriner K, et al. Food Sci. Technol. Int. 19(4), 291-303, (2013)

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Thermodynamic and kinetic processes during the unfolding of BSA in the presence of the mycotoxin patulin. Horváth E, Kálmán N, Pesti M, et al. Acta Biol. Hung. 63(3), 389-98, (2012)

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Selenium supplementation shows protective effects against patulin-induced brain damage in mice via increases in GSH-related enzyme activity and expression. Song E, Su C, Fu J, et al. Life Sci. 109(1), 37-43, (2014)

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A rapid determination of patulin using capillary zone electrophoresis and its application to analysis of apple juices. Güray T, Tuncel M, and Uysal UD J. Chromatogr. Sci. 51(4), 310-7, (2013)

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Interaction with Penicillium expansum enhances Botrytis cinerea growth in grape juice medium and prevents patulin accumulation in vitro. Morales H, Paterson RR, Venâncio A, et al. Lett. Appl. Microbiol. 56(5), 356-60, (2013)

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Effect of the fungal mycotoxin patulin on the chromatin structure of fission yeast Schizosaccharomyces pombe. Horvath E, Nagy G, Turani M, et al. J. Basic Microbiol. 52(6), 642-52, (2012)

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Penicillium species present in Uruguayan salami. Galvalisi U, Lupo S, Piccini J, et al. Rev. Argent. Microbiol. 44(1), 36-42, (2012)

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[Analytical methods for mycotoxins]. Tabata S Shokuhin Eiseigaku Zasshi 53(3), 129-38, (2012)

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3. Patulin. IARC Monographs, (1976) 10, 205

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Merck 14,7053

Beil. 18,V,3,5

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