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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:
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

Signal Word

Danger

Hazard Statements

H300,H315

Hazard Classifications

Acute Tox. 2 Oral - Skin Irrit. 2

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), 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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Effects of various lactones and related compounds on cation transfer in incubated cold-stored human erythrocytes.
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)
Nikita Malhotra et al.
International journal of cardiology, 197, 318-325 (2015-07-08)
A therapeutic window in antiplatelet treatment has been associated with concurrent lowering of bleeding and ischemic risks. Prasugrel and ticagrelor provide potent platelet inhibition, but may increase bleeding. No study has evaluated a personalized therapy with selective use of novel
Peter O Krutzik et al.
Nature chemical biology, 4(2), 132-142 (2007-12-25)
Drug screening is often limited to cell-free assays involving purified enzymes, but it is arguably best applied against systems that represent disease states or complex physiological cellular networks. Here, we describe a high-content, cell-based drug discovery platform based on phosphospecific
Marieke Vansteelandt et al.
Fungal biology, 116(9), 954-961 (2012-09-08)
Genus Penicillium represents an important fungal group regarding to its mycotoxin production. Secondary metabolomes of eight marine-derived strains belonging to subgenera Furcatum and Penicillium were investigated using dereplication by liquid chromatography (LC)-Diode Array Detector (DAD)-mass spectrometry (MS)/MS. Each strain was
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