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P1639

Sigma-Aldrich

Patulin

≥98.0% (HPLC)

Synonym(s):

Clavacin, Clavatin, Expansine, Gigantin, Leucopin, Mycoine C3, Terinin, 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one

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About This Item

Empirical Formula (Hill Notation):
C7H6O4
CAS Number:
149-29-1
Molecular Weight:
154.12
Beilstein/REAXYS Number:
149675
EC Number:
205-735-2
MDL number:
MFCD00005858
UNSPSC Code:
51102829
PubChem Substance ID:
24898227
NACRES:
NA.85

Quality Level

300

assay

≥98.0% (HPLC)

form

powder

solubility

water: 9-11 mg/mL

antibiotic activity spectrum

fungi

mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

OC1OCC=C2OC(=O)C=C12

InChI

1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2

InChI key

ZRWPUFFVAOMMNM-UHFFFAOYSA-N

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General description

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.

Application

Patulin has been used:
  • to study patulin contamination of bottled wine
  • in DNA-damaging activity of patulin in Escherichia coli
  • in molecular cloning and functional characterization of two CYP619 cytochrome P450s involved in biosynthesis of patulin in Aspergillus clavatus

Biochem/physiol Actions

Mycotoxin with anti-bacterial, potassium uptake inhibitory, and possibly carcinogenic activities. 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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300,H315

Hazard Classifications

Acute Tox. 2 Oral - Skin Irrit. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J B KAHN
The Journal of pharmacology and experimental therapeutics, 121(2), 234-251 (1957-10-01)
Birkinshaw, M., et al.
Lancet, 245, 625-625 (1943)
Alicia Rodríguez et al.
International journal of food microbiology, 155(1-2), 10-18 (2012-02-14)
A multiplex real-time PCR (qPCR) method to quantify aflatoxin, ochratoxin A (OTA) and patulin producing molds in foods was developed. For this, the primer pairs F/R-omt, F/R-npstr and F/R-idhtrb and the TaqMan probes, OMTprobe, NPSprobe and IDHprobe targeting the omt-1
Nina Glaser et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(5), 1796-1801 (2012-03-20)
Patulin is a frequently found food contaminant mainly produced by the fungi Aspergillus and Penicillium. Patulin is suspected to be clastogenic, mutagenic, teratogenic and in higher concentrations cytotoxic. Here, we investigate the mechanism of the patulin-induced genotoxicity. Chromosomal damage was
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