2-(3,6-Diacetoxy-2,7-dichloro-9h-xanthen-9-yl)benzoic acid

Base Information

• Chemical Name: 2-(3,6-Diacetoxy-2,7-dichloro-9h-xanthen-9-yl)benzoic acid
• CAS No.: 4091-99-0
• Molecular Formula: C24H16 Cl2 O7
• Molecular Weight: 487.293
• Hs Code.: 29329990
• European Community (EC) Number: 685-843-8
• DSSTox Substance ID: DTXSID9063293
• Nikkaji Number: J413.059F
• Wikidata: Q3026532
• Mol file: 4091-99-0.mol

Synonyms:2',7'-dichlorodihydrofluorescein diacetate;DCDHF-DA;H2DCFDA

Chemical Property of 2-(3,6-Diacetoxy-2,7-dichloro-9h-xanthen-9-yl)benzoic acid

Chemical Property:

• Melting Point: 209-210 °C(lit.)
• Boiling Point: 593.5 °C at 760 mmHg
• PKA: 3.79±0.36(Predicted)
• Flash Point: 312.7 °C
• PSA: 99.13000
• Density: 1.463g/cm³
• LogP: 5.82810
• Storage Temp.: −20°C
• Solubility.: DMF: soluble
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 486.0273082
• Heavy Atom Count: 33
• Complexity: 717

Purity/Quality:

98%,99%, ^*data from raw suppliers

2′,7′-Dichlorofluorescin diacetate ≥97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1=C(C=C2C(C3=CC(=C(C=C3OC2=C1)OC(=O)C)Cl)C4=CC=CC=C4C(=O)O)Cl
• Description: DCFH (commonly known as dichlorofluorescin) is used as an indicator of peroxynitrite formation. DCFH is supplied as the diacetate ester. Following enzymatic or base-catalyzed cleavage of the diacetate groups, it is readily oxidized to the highly fluorescent product dichlorofluorescein (DHF). Peroxynitrite is an efficient mediator of this oxidation and neither NO, superoxide, nor hydrogen peroxide alone appear to oxidize DCFH. Formation of DHF can be monitored by fluorescence spectroscopy using excitation and emission wavelengths of 502 and 523 nm, respectively, or by absorbance spectroscopy at 500 nm (ε = 59,500 M?1cm?1).
• Uses: Cell-permeable fluorogenic probe used to measure reactive oxygen species (ROS) within cells by detection of enzymatically formed hydrogen peroxide. 2',7'-Dichlorodihydrofluorescein as a cell-permeable non-fluorescent probe. It is de-esterified intracellularly and turns to highly fluorescent 2’7’dichlorofluorescein upon oxidation. 2′,7′-Dichlorofluorescin diacetate is a cell-permeable non-fluorescent probe. 2′,7′-Dichlorofluorescin diacetate is de-esterified intracellularly and turns to highly fluorescent 2′,7′-dichlorofluorescein upon oxidation.Applications include sensitive and rapid quantitation of oxygen-reactive species in response to oxidative metabolism; microplate assay for detecting oxidative products in phagocytic cells, and quantitative multiwell myeloid differentiation assay.

Technology Process of 2-(3,6-Diacetoxy-2,7-dichloro-9h-xanthen-9-yl)benzoic acid

There total 1 articles about 2-(3,6-Diacetoxy-2,7-dichloro-9h-xanthen-9-yl)benzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2',7'-dichlorodihydrofluorescein diacetate (2044-85-1) → 2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid (4091-99-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 18h; under 760.051 Torr;

DOI:10.1039/c5cc02192h

Reference yield: 61.0%

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid (4091-99-0) + propargyl alcohol (107-19-7) → C27H18Cl2O7

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/bkcs.12181

Reference yield:

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid (4091-99-0) → 2',7'-dichlorofluorescein (76-54-0)

Guidance literature:

With hemin; d(ATTGTGCGTCATCCCTTACGTCAGTGGAG), screened from Cauliflower mosaic virus (CaMV) 35S promoter; d(CTCCACTGACGTAATGGGTAGGG); d(GGGTTGGGCGGATGACGCACAAT); potassium chloride; ammonium acetate; In water; at 20 ℃; for 0.166667h; pH=7; aq. buffer;

DOI:10.1039/c0cc02933e

upstream raw materials:

2',7'-dichlorodihydrofluorescein diacetate

Downstream raw materials:

2,7-dichlorofluorescein

2-(2,7-dichloro-3,6-dihydroxy-9H-xanthen-9-yl)benzoic acid

2',7'-dichlorofluorescein

Refernces