| Identification | More | [Name]
PATULIN | [CAS]
149-29-1 | [Synonyms]
4-HYDROXY-4H-FURO[3,2-C]PYRAN-2(6H)-ONE
CLAVACIN
HEXADECANOIC ACID TRYPTAMIDE
N-[2-(3-INDOLYL)ETHYL]HEXADECANAMIDE
N-HEXADECANOYLTRYPTAMINE
PALMITIC ACID TRYPTAMIDE
PAT
PATULIN
PATULIN, PENICILLIUM EXPANSUM
(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
2-c)pyran-2(6h)-one,4-hydroxy-4h-furo(
2h-pyran-delta(sup3(6h),alpha)-aceticacid,2,4-dihydroxy-,3,4-lactone
3-c)pyran-2(6h)-one,4-hydroxy-4h-furo(
aceticacid,(2,4-dihydroxy-2h-pyran-3(6h)-ylidene)-,3,4-lactone
clairformin
clavatin
claviform
claviformin
expansin | [EINECS(EC#)]
205-735-2 | [Molecular Formula]
C7H6O4 | [MDL Number]
MFCD00005858 | [Molecular Weight]
154.12 | [MOL File]
149-29-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystals or fine crystalline powder | [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 | [form ]
Crystals or Crystalline Powder | [pka]
11.69±0.20(Predicted) | [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 Reference]
149-29-1(CAS DataBase Reference) | [IARC]
3 (Vol. 40, Sup 7) 1987 | [EPA Substance Registry System]
Patulin (149-29-1) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xn,C,F | [Risk Statements ]
R25:Toxic if swallowed.
R38:Irritating to the skin.
R48/20/22:Harmful: danger of serious damage to health by prolonged exposure through inhalation and if swallowed .
R40:Limited evidence of a carcinogenic effect.
R22:Harmful if swallowed.
R34:Causes burns.
R11:Highly Flammable. | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 3462 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
LV2625000
| [HazardClass ]
6.1(a) | [PackingGroup ]
I | [HS Code ]
29419090 | [Hazardous Substances Data]
149-29-1(Hazardous Substances Data) | [Toxicity]
LD50 s.c. in mice: 10-15 mg/kg (Kinosita, Shikata) |
| Hazard Information | Back Directory | [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]
An inhibitor of protein prenylation | [Uses]
Patulin (PAT), a mycotoxin produced by certain species of Penicillium, Aspergillus, and Byssochlamys, is mainly found in ripe apple and apple products. | [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) 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 |
|
|