4-methoxy-7H-furo[3,2-g]chromen-7-one

• ChemBase编号: 104315
• 分子式: C12H8O4
• 平均质量: 216.18952
• 单一同位素质量: 216.04225874
• SMILES: COc1c2ccc(=O)oc2cc2c1cco2
• Canonical SMILES: COc1c2ccc(=O)oc2cc2c1cco2
• InChI: InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
• InChIKey: BGEBZHIAGXMEMV-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-methoxy-7H-furo[3,2-g]chromen-7-one
• IUPAC传统名: 4-methoxy-7H-furo[3,2-g]chromen-7-one; bergapten
• 别名: 4-甲氧基-7H-呋喃并[3,2-g]苯并吡喃-7-酮; 佛手柑内酯; 5-甲氧基补骨脂素; 4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one; Bergaptan; Bergaptene; Heraclin; Majudin; 5-MOP, Psoraderm-5; 5-METHOXYPSORALEN; Bergapten; 5-Methoxypsoralen; Bergapten; 4-Methoxyfuro[3,2-g]benzopyrane-7-one; Bergapten; 5-Methoxypsoralen; 4-Methoxy-7H-furo[3,2-g]chromen-7-one

登记号

• CAS号: 484-20-8
• EC号: 207-604-5
• MDL号: MFCD00010272
• Beilstein号: 19560
• PubChem SID: 162093037; 24856667; 24883936
• PubChem CID: 2355
• ATC码: D05BA03
• CHEMBL: 24171
• Chemspider ID: 2265
• KEGG ID: D07521
• 美国药典/FDA物质标识码: 4FVK84C92X
• 维基百科标题: Bergapten

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.7848117
• LogD (pH = 7.4): 1.7848117
• Log P: 1.7848117
• 摩尔折射率: 56.8529 cm^3
• 极化性: 22.595345 Å^3
• 极化表面积: 48.67 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Powder; White to Off-White Solid
• 熔点: 156-158°C; 189-193 °C; 190-193 °C; 190-193 °C(lit.)
• 荧光: λex 352 nm; λem 480 nm in methanol

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: LV1300000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 2
• 危险公开号: 45-43; R:45
• 安全公开号: 53-36/37-45; S:28-36/37/39-45-53
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H334-H340-H350
• GHS警示性声明: P201-P261-P308 + P313
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• 保存温度: 2-8°C

药理学性质

• 作用靶点: Others
• 给药途径: Oral
• 生物活性机理: Radiosensitizer; Spasmolytic

产品相关信息

• 纯度: ≥98.0% (HPLC); ≥99.0% (HPLC); 95+%; 97%; 99%
• 级别: analytical standard; for fluorescence
• 成盐信息: Free Base
• 生物来源: Major constit. of bergamot oil (Citrus bergamia), also from Heracleum giganteum and Ammi majus. Widely distributed in the Rutaceae and Umbelliferae
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antihistamine agent; Antiinflammatory; Antipsoriatic; Show spasmolytic props; Used in the treatment of vitiligo
• Empirical Formula (Hill Notation): C12H8O4

详细说明

Sigma Aldrich - 275727

包装
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 65320

Other Notes
DNA 嵌入剂，经紫外辐射形成共价交联1,2,3

Toronto Research Chemicals - B318500

Naturally occurring analog of Psoralen ( P839800) and metabolite of 8-Methoxy Psoralen (M260795). Antipsoriatic.

参考文献

• Honigsmann, H., et al.: Br. J. Dermatol., 101, 369 (1979)
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• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MFN275
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1321A, (nmr)
• Baetcke, E. et al., Ber., 1912, 45, 3705, (struct)
• Glatfelder, A. et al., Helv. Chim. Acta, 1920, 3, 541; 1921, 4, 718, (synth)
• Socias, L. et al., Ber., 1934, 67, 59, (isol)
• Kubiczek, G. et al., Ber., 1937, 70, 1253, (synth)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1369, (occur, deriv)
• Austin, D.J. et al., Phytochemistry, 1973, 12, 1657, (biosynth)
• Boyd, R.K. et al., Can. J. Chem., 1979, 57, 1995, (ms)
• Duddeck, H. et al., Phytochemistry, 1979, 18, 139, (cmr)
• IARC Monog., 1986, 40, 327, (tox, rev)
• Gu, Z. et al., Chem. Pharm. Bull., 1990, 38, 2498, (deriv)
• Ginderow, D., Acta Cryst. C, 1991, 47, 2144, (cryst struct)
• Diawara, M.M. et al., J. Agric. Food Chem., 1995, 43, 723-727, (occur)
• Masuda, T. et al., Phytochemistry, 1998, 47, 13-16, (Bergapten, isol, pmr, cmr)