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149-29-1

149-29-1 Structure

149-29-1 Structure
IdentificationMore
[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 PropertiesBack 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.
[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 DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)
GHS06
[Signal word ]

Danger
[Hazard statements ]

H300-H315
[Precautionary statements ]

P264-P270-P280-P301+P310-P302+P352-P332+P313
[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
[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)
Hazard InformationBack 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
Spectrum DetailBack Directory
[Spectrum Detail]

PATULIN(149-29-1)1HNMR
PATULIN(149-29-1)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Patulin, 99%(149-29-1)
[Sigma Aldrich]

149-29-1(sigmaaldrich)
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