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

• ChemBase编号: 575
• 分子式: C20H12O5
• 平均质量: 332.30628
• 单一同位素质量: 332.06847348
• SMILES: O1C2(c3c(C1=O)cccc3)c1c(Oc3c2ccc(O)c3)cc(O)cc1
• Canonical SMILES: Oc1ccc2c(c1)Oc1c(C32OC(=O)c2c3cccc2)ccc(c1)O
• InChI: InChI=1S/C20H12O5/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,21-22H
• InChIKey: GNBHRKFJIUUOQI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC传统名: fluorescein
• 商标名: Acid Yellow 73; Eosin; Fluorescein Sodium salt; Fluorescein acid; Fluorescein disodium salt; Fluorescein disodium salt dihydrate; Fluorescein sodium; Fluorescein, Disodium Salt, Fluorescein, disodium salt; Fluorescite; Funduscein-25; Uranin; Uranine
• 别名: 酸性黄 73; 荧光素; 3',6'-Dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one; 3',6'-Dihydroxyfluoran; 2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic Acid; C.I. 45350:1; C.I. Solvent Yellow 94; D and C Yellow No. 7; D&C Yellow No. 7; Fluorescein Acid; Japan Yellow 201; Japan Yellow No. 201; NSC 667256; Yellow Fluorescein; 3',6'-Dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one; 3',6'-Fluorandiol; 3,6-Dihydroxyspiro[xanthene-9,3'-phthalide]; 9-(o-Carboxyphenyl)-6-hydroxy-3-isoxanthenone; C.I. 45350.1; Fluorescein; Deoxyribonucleic acid; Fluorescein Low Range DNA standard; Fluorescein; Fluorescein (free acid); Solvent Yellow 94; Acid Yellow 73; Fluorescein; resorcinolphthalein; C.I. 45350, solvent yellow 94, D & C yellow no. 7, angiofluon; Japan yellow 201, soap yellow

登记号

• CAS号: 2321-07-5
• EC号: 219-031-8
• MDL号: MFCD00005050
• Beilstein号: 94324
• 默克索引号: 144159
• PubChem SID: 24859566; 46504703; 24870483; 160964038; 24894822
• PubChem CID: 16850
• CHEBI ID: 31624
• CHEMBL: 177756
• Chemspider ID: 15968
• DrugBank ID: DB00693
• KEGG ID: D01261
• 医学主题词(MeSH): Fluorescein
• 美国药典/FDA物质标识码: TPY09G7XIR
• 维基百科标题: Fluorescein
• Color Index Number: 45350; 45350:1

理论计算性质

JChem

• Acid pKa: 8.719013
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.8800821
• LogD (pH = 7.4): 3.8598857
• Log P: 3.8803427
• 摩尔折射率: 91.2201 cm^3
• 极化性: 34.4024 Å^3
• 极化表面积: 75.99 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.64
• LOG S: -4.11
• 溶解度: 2.55e-02 g/l

分子性质

理化性质

• 溶解度: 600 mg/mL (sodium salt); DMSO; Slightly in water
• 外观: Red Solid
• 熔点: >300°C; 314 - 316°C; 320 °C(lit.); 320°C
• 密度: 1.602 g/mL
• 紫外吸收波长: λmax 496 nm
• 疏水性(logP): 3.4

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: LM5075000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36; R:36
• 安全公开号: 26; 26-60; S:26; S26 S36
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H319
• GHS警示性声明: P280-P264-P305+P351+P338-P337+P313; P305 + P351 + P338
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... PTPN1(5770), PTPRF(5792)

产品相关信息

• 纯度: ~96%; 90+%; 95+%
• 级别: Reag. Ph. Eur.
• 主要成分: Dye content, 95%
• 适用性: in accordance for electrophoresis test; in accordance for TLC; passes test for TLC; passes test for UV spectrum
• 燃烧残渣: ≤0.25% (as SO4)
• 使用说明: sufficient for 100 tests
• Empirical Formula (Hill Notation): C20H12O5

详细说明

MP Biomedicals - 02151155

C.I. 45350.1
Free Acid
Crystalline
Purity: ~96%

DrugBank - DB00693

• Drug Groups: approved
• Description: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium, such as the aqueous humor, and is used therapeutically as a diagnostic aid in corneal injuries and corneal trauma. It has been approved by FDA for use in externally applied drugs and cosmetics. (From Merck Index, 12th ed; American Medical Association Drug Evaluations; 1995, p2275)
• Indication: For diagnostic imaging. Primarily indicated in diagnostic fluorescein angiography or angioscopy of the fundus and of the iris vasculature.
• Affected Organisms: Humans and other mammals
• Absorption: Rapidly distributed
• Protein Binding: 85%
• Elimination: Fluorescein and its metabolites are mainly eliminated via renal excretion.
• Distribution: * 0.5 L/kg
• Clearance: * renal cl=1.75 mL/min/kg [After IV administration]; * hepatic cl=1.50 mL/min/kg [After IV administration]
• References: Noga EJ, Udomkusonsri P: Fluorescein: a rapid, sensitive, nonlethal method for detecting skin ulceration in fish. Vet Pathol. 2002 Nov;39(6):726-31. [Pubmed]
• External Links: Wikipedia; RxList

Sigma Aldrich - F2456

包装
2.5, 100, 500 g in glass bottle

Sigma Aldrich - 46978

Components
1 vial pBR 322 Hin F1 digest in 10 mM TRIS, pH 8.0, 1 mM EDTA (50 fmol/μl each fragment; 0.14 μg/μl), 200 μl1 vial 5× loading buffer (12.5% Ficoll, 0.05% bromophenol blue, 50 mM TRIS, pH 8.0, 5 mM EDTA), 500 μl
General description
pBR 322 Hin F1 digest, 10 Fluorescein end-labeled fragments: 75, 154, 220/221, 296, 334, 396, 504, 517, 1632 bpdetection: Exc.: 302 nm, Em.: 521 nm

Sigma Aldrich - 32615

General description
请访问 滴定中心 了解更多信息。

Toronto Research Chemicals - F485250

A fluorescent tracer used for many applications. It is used in ophthalmology as a tool in the diagnosis of corneal abrasions, corneal ulcers and herpetic corneal infections. It can attach to certain biologically active molecules, thus allowing biologists

参考文献

• Noga EJ, Udomkusonsri P: Fluorescein: a rapid, sensitive, nonlethal method for detecting skin ulceration in fish. Vet Pathol. 2002 Nov;39(6):726-31. Pubmed
• Drees, B.L. et al.: J. Biol. Chem., 271, 32168 (1996)
• Can. Med. Assoc. J., 80, 997 (1996)
• Taki, M. et al.: Prot. Eng. Des. Select., 17, 119 (1996)