PATULIN

PATULIN Basic information
Product Name:PATULIN
Synonyms:(2,4-dihydroxy-2h-pyran-3(6h)-ylidene)aceticacid-3,4-lactone;2,4-dihydroxy-2h-pyran-delta-3(6h),alpha-aceticacid-3,4-lactone;N-HEXADECANOYLTRYPTAMINE;PALMITIC ACID TRYPTAMIDE;PATULIN;PATULIN, PENICILLIUM EXPANSUM;PAT;N-[2-(3-INDOLYL)ETHYL]HEXADECANAMIDE
CAS:149-29-1
MF:C7H6O4
MW:154.12
EINECS:205-735-2
Product Categories:antibiotic;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:149-29-1.mol
PATULIN Structure
PATULIN Chemical Properties
Melting point 108-111 °C
alpha D21 -6.2° (chloroform)
Boiling point 197.46°C (rough estimate)
density 1.1993 (rough estimate)
refractive index 1.4300 (estimate)
Fp 2℃
storage temp. −20°C
solubility ethyl acetate: soluble50mg/mL
pka11.69±0.20(Predicted)
form Crystals or Crystalline Powder
color White
Merck 13,7125
BRN 149675
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
CAS DataBase Reference149-29-1(CAS DataBase Reference)
IARC3 (Vol. 40, Sup 7) 1987
EPA Substance Registry SystemPatulin (149-29-1)
Safety Information
Hazard Codes T,Xn,C,F
Risk Statements 25-38-48/20/22-40-22-34-11-36-20/21/22-67-36/38-20-63
Safety Statements 45-36/37-36/37/39-26-16
RIDADR UN 3462 6.1/PG 2
WGK Germany 3
RTECS LV2625000
HazardClass 6.1(a)
PackingGroup I
HS Code 29419090
Hazardous Substances Data149-29-1(Hazardous Substances Data)
ToxicityLD50 s.c. in mice: 10-15 mg/kg (Kinosita, Shikata)
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
PATULIN Usage And Synthesis
DescriptionSpergillus and Penicillium species. Patulin is also an animal carcinogen, inhibits K1-uptake into erythrocytes, and inhibits various forms of Na1/K1-ATPase.
Chemical Propertieswhite crystals or fine crystalline powder
UsesPatulin (PAT), a mycotoxin produced by certain species of Penicillium, Aspergillus, and Byssochlamys, is mainly found in ripe apple and apple products.
UsesAn inhibitor of protein prenylation
DefinitionChEBI: A furopyran and lactone that is 2H-pyran-3(6H)-ylidene)acetic acid which is syubstituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give he corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.
Purification MethodsCrystallise patulin from *C6H6, Et2O, EtOH or chloroform. It sublimes at 90o/high vacuum [Bergel et al. J Chem Soc 415 1944]. [Beilstein 18 III/IV 1184, 18/3 V 5.] (Highly TOXIC).
References1) Jin et al. (2016), p53 activation contributes to patulin-induced nephrotoxicity via modulation of reactive oxygen species generation; Sci. Rep., 6 24455 2) Zouaoui et al. (2016), Cytotoxic effects induced by patulin, sterigmatocystin and beauvericin on CHO-K1 cells; Food Chem. Toxicol., 89 92 3) Boussabbeh et al. (2016), Tissue oxidative stress induced by patulin and protective effect of crocin; Neurotoxicology, 53 343 4) Pillay et al. (2015), Patulin triggers NRF2-meditated survival mechanisms in kidney cells; Toxicon, 99 1 5) Boussabbeh et al. (2015), Patulin induces apoptosis through ROS-mediated endoplasmic reticulum stress pathway; Toxicol. Sci., 144 328
PATULIN Preparation Products And Raw materials
Ethyl vinyl ether 2-Ethoxypropene 2,5-Dihydrofuran 2-Methylene-1,3-propanediol 2(5H)-Furanone 5,6-DIHYDRO-4-METHOXY-2H-PYRAN VINYL ACRYLATE 5-methylenefuran-2(5H)-one PATULIN Vinyl crotonate VINYL FORMATE CIS-2-PENTEN-1-OL TRANS-1,4-DIMETHOXY-2-BUTENE Vinyl acetate 4-METHYL-2(5H)-FURANONE Allyl ether (2Z,4Z)-HEXA-2,4-DIENE-1,6-DIOL Isopropenyl acetate

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