5-amino-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

• ChemBase编号: 102444
• 分子式: C20H13NO5
• 平均质量: 347.32092
• 单一同位素质量: 347.07937252
• SMILES: Nc1cc2c(cc1)C1(OC2=O)c2c(Oc3c1ccc(O)c3)cc(O)cc2
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3ccc(c2)N)ccc(c1)O
• InChI: InChI=1S/C20H13NO5/c21-10-1-4-14-13(7-10)19(24)26-20(14)15-5-2-11(22)8-17(15)25-18-9-12(23)3-6-16(18)20/h1-9,22-23H,21H2
• InChIKey: GZAJOEGTZDUSKS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-amino-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC传统名: 5-amino-3',6'-dihydroxyspiro[2-benzofuran-1,9'-xanthene]-3-one
• 别名: 5-Aminofluorescein; FLUORESCEIN AMINE ISOMER I; 1-AMINOFLUORESCEIN; Fluoresceinamine, Isomer 1; Fluoresceinamine isomer I; 5-Aminofluorescein; Fluoresceinamine, isomer I

登记号

• CAS号: 3326-34-9
• EC号: 222-043-6
• MDL号: MFCD00005052
• Beilstein号: 48395
• PubChem SID: 162088661; 24852015
• PubChem CID: 76845

理论计算性质

• Acid pKa: 8.719013
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 3.0507562
• LogD (pH = 7.4): 3.0309548
• Log P: 3.0514169
• 摩尔折射率: 95.9205 cm^3
• 极化性: 35.55254 Å^3
• 极化表面积: 102.01 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; Methanol
• 外观: Dark Red Solid
• 熔点: 223 °C (dec.)(lit.)
• 紫外吸收波长: λmax 496 nm

安全信息

• 保存条件: 2-8°C, Desiccate
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

产品相关信息

• 纯度: ≥90% (HPLC)
• 级别: for fluorescence; p.a.
• 杂质: ≤1% 6-isomer (HPLC)
• Empirical Formula (Hill Notation): C20H13NO5

详细说明

MP Biomedicals - 05209359

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101709

Dark Red (for synthesis of Fluorescein Isothiocyanate)

Sigma Aldrich - 201626

包装
1, 5 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 07980

Application
The two isomers are produced by the usual synthesis. Most publications imply they are interchangeable when used for the preparation of the isothiocyanate for fluorescent antibody work. In fact, most commercial preparations are not even labeled as to whether or not they are mixtures.
Other Notes
All known glycosaminoglycuronans react with this fluorescein derivative to yield fluorescent derivatives1
Note: Do not confuse with fluorescamine.

Toronto Research Chemicals - F485300

Fluorescent labeling reagent for proteins. Used in the fluorescent antibody technique for rapid identification of pathogens.

参考文献

• Riggs, H.J.L., et al.: Amer. J. Pathol., 34, 1081 (1958)
• Mann, K.G. and Fish, W.W., Methods in Enz., 26, 28 (1958)