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PATULIN

Product NamePATULIN
CAS149-29-1
MFC7H6O4
MW154.12
EINECS205-735-2
MOL File149-29-1.mol

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)
Flash point	2℃
storage temp.	−20°C
solubility	ethyl acetate: soluble50mg/mL
pka	11.69±0.20(Predicted)
form	Crystals or Crystalline Powder
color	White
Merck	13,7125
BRN	149675
Henry's Law Constant	9.0×10⁴ mol/(m³Pa) at 25℃, HSDB (2015)
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.
Major Application	cleaning products cosmetics food and beverages personal care
InChI	1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2
InChIKey	ZRWPUFFVAOMMNM-UHFFFAOYSA-N
SMILES	OC1OCC=C2OC(=O)C=C12
CAS DataBase Reference	149-29-1(CAS DataBase Reference)
IARC	3 (Vol. 40, Sup 7) 1987
EPA Substance Registry System	Patulin (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
Storage Class	3 - Flammable liquids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 Flam. Liq. 2
Hazardous Substances Data	149-29-1(Hazardous Substances Data)
Toxicity	LD50 s.c. in mice: 10-15 mg/kg (Kinosita, Shikata)

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English

Usage And Synthesis

Description

Spergillus and Penicillium species. Patulin is also an animal carcinogen, inhibits K1-uptake into erythrocytes, and inhibits various forms of Na1/K1-ATPase.

Chemical Properties

white crystals or fine crystalline powder

Uses

Patulin (PAT), a mycotoxin produced by certain species of Penicillium, Aspergillus, and Byssochlamys, is mainly found in ripe apple and apple products.

Uses

An inhibitor of protein prenylation

Definition

ChEBI: 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 Methods

Crystallise 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).

References

[1] HUAN JIN. p53 activation contributes to patulin-induced nephrotoxicity via modulation of reactive oxygen species generation.[J]. Scientific Reports, 2016: 24455. DOI:10.1038/srep24455
[2] NIDHAL ZOUAOUI . Cytotoxic effects induced by patulin, sterigmatocystin and beauvericin on CHO–K1 cells[J]. Food and Chemical Toxicology, 2016, 89: Pages 92-103. DOI:10.1016/j.fct.2016.01.010
[3] MANEL BOUSSABBEH . Tissue oxidative stress induced by patulin and protective effect of crocin[J]. Neurotoxicology, 2016, 53: Pages 343-349. DOI:10.1016/j.neuro.2015.11.005
[4] Y. PILLAY . Patulin triggers NRF2-mediated survival mechanisms in kidney cells[J]. Toxicon, 2015, 99: Pages 1-5. DOI:10.1016/j.toxicon.2015.03.004
[5] MANEL BOUSSABBEH. Patulin induces apoptosis through ROS-mediated endoplasmic reticulum stress pathway.[J]. Toxicological Sciences, 2015, 144 2: 328-337. DOI:10.1093/toxsci/kfu319

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