4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one

• ChemBase ID: 105386
• Molecular Formular: C7H6O4
• Molecular Mass: 154.12014
• Monoisotopic Mass: 154.02660867
• SMILES: OC1OCC=C2OC(=O)C=C12
• Canonical SMILES: O=C1OC2=CCOC(C2=C1)O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one
• IUPAC Traditional name: patulin
• Synonyms: Patulin; PAT; 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one; Patulin solution; PATULIN; 2-Hydroxy-3,7-dioxabicyclo[4.3.0]nona-5,9-dien-8-one; Clairformin; Claviform; Expansine; Clavacin; Clavatin; Expansin; Gigantin; Leucopin; Patuline; Claviformin; DL-Patulin; Mycoin; Mycoin C; Mycoin C3; NSC 32951; NSC 8120; Penicidin; Terinin; 4-羟基-4H-呋[3,2-c]吡喃-2(6H)-酮; 棒曲霉素; 棒曲霉素 溶液

Database IDs

• CAS Number: 149-29-1
• EC Number: 200-835-2; 205-735-2
• MDL Number: MFCD00005858
• Beilstein Number: 149675
• PubChem SID: 162092550; 24898227; 24860920
• PubChem CID: 4696
• CHEMBL: 294018
• Chemspider ID: 4534
• KEGG ID: C16748
• Unique Ingredient Identifier: 95X2BV4W8R
• Wikipedia Title: Patulin

CALCULATED PROPERTIES

• Acid pKa: 11.653255
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.3772453
• LogD (pH = 7.4): -0.3772692
• Log P: -0.377245
• Molar Refractivity: 37.0348 cm^3
• Polarizability: 13.874448 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Soluble in water
• Apperance: Compact prisms; Off-White Solid
• Melting Point: 110°C; 97-99°C
• Flash Point: 2 °C; 35.6 °F

Safety Information

• Storage Condition: 0°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: LV2625000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1648; 2811; 3462
• German water hazard class: 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 11-20/21/22-36; 25-38; R:25
• Safety Statements: 16-36/37; 45; R; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H319-H332; H300-H315
• GHS Precautionary statements: P210-P280-P305 + P351 + P338; P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Eyeshields, Gloves
• RID/ADR: UN 1648 3/PG 2; UN 3462 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)
• Concentration: 100 μg/mL in acetonitrile
• Grade: analytical standard, for environmental analysis
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C7H6O4

DETAILS

MP Biomedicals - 02159989

A mycotoxin which blocks the farnesylation of proteins in a cell free assay. It inhibits the incorporation of ^3 H-mevalonate into proteins found in complete cells.

Sigma Aldrich - P1639

Application
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. It is used to study patulin contamination of bottled wine 1, DNA-damaging activity of patulin in Escherichia coli.2, and molecular cloning and functional characterization of two CYP619 cytochrome P450s involved in patulin biosynthesis3.
Biochem/physiol Actions
Patulin is genotoxic and may be carcinogenic. It is an inhibitor of potassium uptake and an inducer of ion flux across cell membranes, potentially involving Na+-K+ dependent ATPase. It induces intra- and intermolecular protein crosslinking. CYP619 cytochrome P450s are involved in biosynthesis of patulin in Aspergillus clavatus3.

Sigma Aldrich - 34127

General description
Certan Vial

Toronto Research Chemicals - P206500

Patulin (PAT), a mycotoxin produced by certain species of Penicillium, Aspergillus, and Byssochlamys, is mainly found in ripe apple and apple products. Patulin-induced genotoxicity and modulation of glutathione in Hep G2 cells. Antibiotic.

REFERENCES

• Miura, S., et al., FEBS Lett , 318 : 88 (1993).
• POSSIBLE CARCINOGEN!
• Scott, P., et al.: J. Agric. Food Chem., 20, 450 (1972)
• Aden, D., et al.: Nature, 282, 615 (1972)
• Surralles, J., et al.: Mutat. Res., 341, 169 (1972)
• Alves, I., et al.: Mutagenesis, 15, 229 (1972)
• Liu, B., et al.: Toxicol. Appl. Pharmacol., 191, 255 (