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

• ChemBase编号: 105386
• 分子式: C7H6O4
• 平均质量: 154.12014
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-hydroxy-2H,4H,6H-furo[3,2-c]pyran-2-one
• IUPAC传统名: patulin
• 别名: 4-羟基-4H-呋[3,2-c]吡喃-2(6H)-酮; 棒曲霉素; 棒曲霉素 溶液; 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

登记号

• CAS号: 149-29-1
• EC号: 200-835-2; 205-735-2
• MDL号: MFCD00005858
• Beilstein号: 149675
• PubChem SID: 24898227; 162092550; 24860920
• PubChem CID: 4696
• CHEMBL: 294018
• Chemspider ID: 4534
• KEGG ID: C16748
• 美国药典/FDA物质标识码: 95X2BV4W8R
• 维基百科标题: Patulin

理论计算性质

• Acid pKa: 11.653255
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -0.3772453
• LogD (pH = 7.4): -0.3772692
• Log P: -0.377245
• 摩尔折射率: 37.0348 cm^3
• 极化性: 13.874448 Å^3
• 极化表面积: 55.76 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; Soluble in water
• 外观: Compact prisms; Off-White Solid
• 熔点: 110°C; 97-99°C
• 闪点: 2 °C; 35.6 °F

安全信息

• 保存条件: 0°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS编号: LV2625000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1648; 2811; 3462
• 德国WGK号: 2; 3
• 联合国危险货物等级: 3; 6.1
• 联合国危险货物包装类别(PG): 2; II
• 澳大利亚Hazchem: 2XE
• 危险公开号: 11-20/21/22-36; 25-38; R:25
• 安全公开号: 16-36/37; 45; R; S:28-29-36/37/39-45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS02; GHS06; GHS07
• GHS警示词: Danger
• GHS危险声明: H225-H302-H312-H319-H332; H300-H315
• GHS警示性声明: P210-P280-P305 + P351 + P338; P264-P301 + P310
• 个人保护装置: 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
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (TLC)
• 浓度: 100 μg/mL in acetonitrile
• 级别: analytical standard, for environmental analysis
• 产品质量级别: PREMIUM
• Empirical Formula (Hill Notation): C7H6O4

详细说明

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.

参考文献

• 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 (